San Gimignano • Volterra • Montepulciano • Pienza • Montalcino • Cortona • More Tuscan Sights
Map: Tuscan Hill Towns Public Transportation
Sights and Experiences in Montepulciano
Tuscany is rich in history, and proud locals will remind you that their ancestors, the Etruscans, were thriving long before anyone had heard of Julius Caesar. The region offers a delightful mix of scenic beauty and rich history...and a taste of the rustic Italian good life.
Many of the hill towns—so emblematic of Tuscany—trace their roots to Etruscan times (well before ancient Rome). Others date from the fall of Rome, when barbarian invasions chased lowland townsfolk to the hills, where they built fortified communities. The Middle Ages were formative times for many cities, when warring factions divided towns between those loyal to the pope (Guelphs) and to the Holy Roman Emperor (Ghibellines). Cities developed monumental defensive walls and built great towers. Then, the Black Death swept through Tuscany in 1348 and devastated the region. The plague, plus the increasing dominance of Florence, turned many bustling cities into docile backwaters. Ironically, what was bad news in the 14th century is good news today: The hill towns enjoy a tourist-fueled affluence and retain a unique, medieval charm.
Tuscan towns are best enjoyed by adapting to the pace of the countryside. So, slow...down...and savor the delights that this region offers. Spend the night if you can, as many hill towns are mobbed by day-trippers from Florence and Siena.
But how in Dante’s name does a traveler choose from Italy’s hundreds of hill towns? I’ve listed some of my favorites in this chapter. The one(s) you visit will depend on your interests, time, and mode of transportation.
Multitowered San Gimignano is a classic, but because it’s such an easy hill town to visit (about 1.5 hours by bus from Florence), peak-season crowds can overwhelm its charms. For rustic vitality not completely trampled by tourist crowds, out-of-the-way Volterra is the clear winner. Wine aficionados head for Montalcino and Montepulciano—each a happy gauntlet of wine shops and art galleries (Montepulciano being my favorite). Fans of architecture and urban design appreciate Pienza’s well-planned streets and squares. Those enamored by Frances Mayes’ memoir (Under the Tuscan Sun) make the pilgrimage to Cortona.
One of the greatest Tuscan treats—the food—varies wildly depending on where you are. The areas around Florence and Siena are famed for serving hearty “farmer food,” but as you move west, dishes become lighter, based more on seafood and grains. Each town proudly boasts local specialties—ask for the specialità della città. While Siena is the town that excels at sweets, you can find good local desserts anywhere (watch for the phrase “fatta in casa,” which means it’s homemade). Wine is good throughout Tuscany, with pleasing selections for both amateurs and connoisseurs. (See “Wine Labels and Lingo” on here for a description of Tuscan wines.)
Most hill towns are easier and more efficient to visit by car.
Traveling by public transportation is cheap and connects you with the locals. While trains link some of the towns, hill towns—being on hills—don’t quite fit the railroad plan. Stations are likely to be in the valley a couple of miles from the town center, usually connected efficiently by a local bus.
Buses are often the only public-transportation choice to get between small hill towns. But, as with trains, they don’t always drive up into the town itself. Fortunately, bus stations are sometimes connected to the town by escalator or elevator.
Buy bus tickets at newsstands or tobacco shops (with the big T signs). Confirm the departure point (“Dov’è la fermata?”)—some piazzas have more than one bus stop, so double-check that the posted schedule lists your destination and departure time. In most cases, orange buses are local city buses, and blue buses are for long distances.
Once the bus arrives, confirm the destination with the driver. You are expected to stow big backpacks underneath the bus (open the luggage compartment yourself if it’s closed).
Sundays and holidays are problematic; even from cities such as Siena, schedules are sparse, departing buses are jam-packed, and ticket offices are often closed. Plan ahead and buy your ticket in advance. Most travel agencies book bus and train tickets with little or no commission.
If you’re pinched for time, it makes sense to narrow your focus to one or two hill towns, or rent a car to see more.
Exploring small-town Tuscany by car can be a great experience. But since a car is an expensive, worthless headache in Florence and Siena, wait to pick up your car until the last big city you visit (or pick it up at the nearest airport to avoid big-city traffic). Then use the car for lacing together the hill towns and exploring the countryside. For more on car rentals and driving in Italy, see the appendix.
A big, detailed regional road map (buy one at a newsstand or gas station) and a semiskilled navigator are essential. Freeways (such as the toll autostrada and the non-toll superstrada) provide the fastest way to connect two points, but the smaller roads, including the super-scenic S-222, which runs through the heart of the Chianti region (connecting Florence and Siena), are more rewarding. For more joyrides—from Siena to Montalcino, and from Montalcino to Montepulciano—see “The Crete Senese” on here.
Parking throughout this region can be challenging. Some towns don’t allow visitors to park in the city center, so you’ll need to leave your car outside the walls and walk into town. Signs reading Zona Traffico Limitato (ZTL)—often above a red circle—mark areas where no driving or parking is allowed. Parking lots, indicated by big blue P signs, are usually free and plentiful outside city walls (and in some cases, are linked to the town center by elevators or escalators). In some towns, you can park on the street; nearby kiosks sell “pay and display” tickets. In general, white lines indicate free parking, blue lines mean you have to pay, and yellow lines are spaces reserved for local residents. To reduce the threat of theft (no guarantees, though), choose a parking lot over street parking when possible. Your hotelier can also recommend safe parking options.
Smaller towns offer few hotels to choose from. Prices are lower than in Florence, but a nice double will still run about €80, including breakfast. Many towns have an abundance of affitta camere, or rental rooms. This can be anything from a set of keys and a basic bed to a cozy B&B with your own Tuscan grandmother. TIs book rooms and apartments and have lists of each. Private rooms are generally a good budget option, but since they vary in quality, shop around to find the best value. It’s always OK to ask to see the room before you commit. Apartments usually offer a couple of bedrooms, a sitting area, and a teensy cucinetta, typically stocked with dishes and flatware—a great value for families traveling together who’d rather cook than eat out all the time.
Agriturismo (agricultural tourism), or rural B&Bs, began in the 1980s as a way to allow small farmers in the countryside to survive in a modern economy where, like in the US, so many have been run out of business by giant agricultural corporations. By renting rooms to travelers, farmers can remain on their land and continue to produce food. A peaceful home base for exploring the region, these rural Italian B&Bs are ideal for those traveling by car—especially families.
It’s wise to book several months in advance for high season (May-Sept). Weeklong stays are preferred in July and August, but shorter stays are possible off-season. To sleep cheaper, avoid peak season. A farmhouse that rents for as much as $2,000 a week in July can go for as little as $700 in late September or October. In the winter, you might be charged extra for heat, so confirm the price ahead of time. Payment policies vary, but generally a 25 percent deposit is required (lost if you cancel), and the balance is due one month before arrival.
As the name implies, agriturismi are in the countryside, although some are located within a mile of town. Most are family-run. Agriturismi vary dramatically in quality—some properties are rustic, while others are downright luxurious, offering amenities such as swimming pools and riding stables. The rooms are usually clean and comfortable. Breakfast is often included, and mezza pensione (half-pension, which in this case means a home-cooked dinner) might be built into the price whether you want it or not. Most places serve tasty homegrown food; some are vegetarian or organic, others are gourmet. Kitchenettes are often available to cook up your own feast.
To qualify officially as an agriturismo, the farm must still generate more money from its farm activities, thereby ensuring that the land is worked and preserved. Some farmhouse B&Bs aren’t working farms, but are still fine places to stay. Many people who think they want agriturismi are really looking for countryside B&Bs and villas that offer a bit more upscale comfort (while skipping the farm smells and sounds). If you want the real thing, make sure the owners call their place an agriturismo.
• To sleep cheap, avoid peak season. Rental prices follow the old rule of supply and demand. Prices that are sky-high in summer can drop dramatically in fall.
• Make sure your trip fits their requirements. Many properties rent on a traditional Saturday-to-Saturday time period. You might be unable to rent for a different or shorter time, especially during peak season.
• If you want amenities, be willing to pay more. A swimming pool can add substantially to the cost, but at the height of summer, could be worth every extra euro, particularly if you’re bringing kids.
• Consider renting a rural apartment rather than an entire villa or farmhouse. Often the owners have renovated an original rambling farmhouse or medieval estate into a series of well-constructed apartments with private kitchens, bathrooms, living areas, and outdoor terraces. They usually share a common pool.
• You will need private transportation, such as a rental car, to fully enjoy—or even reach—your accommodations.
• To make the most of your time, ask an expert—the owner—for suggestions on restaurants, sights, and activities. Make sure you know how to operate the appliances.
• Slow down. One of the joys of staying for at least a week in one location is you can develop a true dolce far niente (sweetness of doing nothing) attitude. If it rains, grab a book from the in-house library and curl up on the sofa.
• While your time in the countryside may not be action-packed, staying put in one spot leaves you open to the unexpected pleasures that come when you just let the days unwind without a plan.
In this chapter, I’ve listed a broad range of options under the towns that they’re nearest to, but there are many, many more. Local TIs can give you a list of places in their area, and many agriturismi now have their own websites. For a sampling, visit www.agriturismoitaly.it or search online for agriturismo. One booking agency among many is Farm Holidays in Tuscany (closed Sat-Sun, tel. 0564-417-418, www.byfarmholidays.com, info@byfarmholidays.com).
Two fine hill towns—one famous, the other underrated—sit in the middle of the triangle formed by three major destinations: Florence, Siena, and Pisa. If driving between those cities, it makes sense to detour either to picturesque but touristy San Gimignano, or charming and authentic-feeling Volterra. (Or you could use one of them as a home base for reaching the bigger towns.) While they’re only about a 30-minute drive apart, they’re poorly connected to each other by public transit (requiring an infrequent two-hour connection); if you’re relying on buses, San Gimignano is easier to reach, but Volterra rewards the additional effort.
The epitome of a Tuscan hill town, with 14 medieval towers still standing (out of an original 72), San Gimignano (sahn jee-meen-YAH-noh) is a perfectly preserved tourist trap. There are no important interiors to sightsee, and the town is packed with crass commercialism. The locals seem spoiled by the easy money of tourism, and most of the rustic is faux. The fact that this small town supports two torture museums is a comment on the caliber of the masses who choose to visit. But San Gimignano is so easy to reach and visually so beautiful that it remains a good stop. It’s enchanting at night, when it’s yours alone. For this reason, San Gimignano is an ideal place to go against the touristic flow—arrive late in the day, enjoy it at twilight, then take off in the morning before the deluge begins.
In the 13th century—back in the days of Romeo and Juliet—feuding noble families ran the hill towns. They’d periodically battle things out from the protection of their respective family towers. Pointy skylines, like San Gimignano’s, were the norm in medieval Tuscany.
San Gimignano’s cuisine is mostly what you might find in Siena—typical Tuscan home cooking. Cinghiale (cheeng-GAH-lay, boar) is served in almost every way: stews, soups, cutlets, and, my favorite, salami. Most shops will give you a sample before you commit to buying. The area is well known for producing some of the best saffron in Italy (collected from the purple flowers of Crocus sativus); you’ll find the spice for sale in shops (it’s fairly expensive) and as a flavoring in meals at finer restaurants. Although Tuscany is normally a red-wine region, the most famous Tuscan white wine comes from here: the inexpensive, light, and fruity Vernaccia di San Gimignano. Look for the green “DOCG” label around the neck for the best quality (see “Wines Labels and Lingo” on here).
While the basic ▲▲▲ sight here is the town of San Gimignano itself, there are a few worthwhile stops. From the town gate, head straight up the traffic-free town’s cobbled main drag to Piazza della Cisterna (with its 13th-century well). The town sights cluster around the adjoining Piazza del Duomo.
The helpful TI is in the old center on Piazza del Duomo (daily March-Oct 10:00-13:00 & 15:00-19:00, Nov-Feb 10:00-13:00 & 14:00-18:00, free maps, sells bus tickets, books rooms, handles VAT refunds, tel. 0577-940-008, www.sangimignano.com).
If interested, ask if the TI is still offering a two-hour guided walk in English and Italian on weekends; if they are, book it the day before by 18:00 (April-Oct Sat-Sun at 11:00, €20; includes admission either to the Duomo or to the Civic Museum and Tower; pay and meet at TI). They also offer a two-hour minibus tour to a countryside winery (€20, April-Oct Tue and Thu at 17:00).
The bus stops at the main town gate, Porta San Giovanni. There’s no baggage storage anywhere in town, so you’re better off leaving your bags in Siena or Florence.
You can’t drive within the walled town. There are three pay lots a short walk outside the walls: The handiest is Parcheggio Montemaggio, just outside Porta San Giovanni (€2/hour, €20/day). The one below the roundabout and Co-op supermarket, called Parcheggio Giubileo, is least expensive (€1.50/hour, €6/day). And at the north end of town, by Porta San Jacopo, is Parcheggio Bagnaia (€2/hour, €15/day). Note that some lots—including the one directly in front of the Co-op and the one just outside Porta San Matteo—are designated for locals and have a one-hour limit for tourists.
Market Day: Thursday is market day on Piazza del Duomo (8:00-13:00), but for local merchants, every day is a sales frenzy.
Services: A public WC is just off Piazza della Cisterna (€0.50); others are at the Rocca fortress, just outside Porta San Matteo, and at the Parcheggio Bagnaia parking lot.
Shuttle Bus: A little electric shuttle bus does its laps all day from Porta San Giovanni to Piazza della Cisterna to Porta San Matteo. Route #1 runs back and forth through town; route #2—which runs only in summer—conveniently connects the three parking lots to the town center. Each route runs about hourly (€0.75 one-way, €1.50 for all-day pass, buy ticket in advance from TI or tobacco shop, possible to buy all-day pass on bus).
(See “San Gimignano” map, here.)
This quick walking tour will take you across town, from the bus stop at Porta San Giovanni through the town’s main squares to the Duomo, and on to the Sant’Agostino Church.
• Start, as most tourists do, at the Porta San Giovanni gate at the bottom end of town.
Porta San Giovanni: San Gimignano lies about 25 miles from both Siena and Florence, a good stop for pilgrims en route to those cities, and on a naturally fortified hilltop that encouraged settlement. The town’s walls were built in the 13th century, and gates like this helped regulate who came and went. Today, modern posts keep out all but service and emergency vehicles. The small square just outside the gate features a memorial to the town’s WWII dead. Follow the pilgrims’ route (and flood of modern tourists) through the gate and up the main drag.
About 100 yards up, on the right, is a pilgrims’ shelter (12th-century, Pisan Romanesque). The eight-pointed Maltese cross indicates that this was built by the Knights of Malta, whose early mission (before they became a military unit) was to provide hospitality for pilgrims. It was one of 11 such shelters in town. Today, only the wall of this shelter remains.
• Carry on past all manner of touristy rip-off shops, up to the town’s central Piazza della Cisterna. Sit on the steps of the well.
Piazza della Cisterna: The piazza is named for the cistern that is served by the old well standing in the center of this square. A clever system of pipes drained rainwater from the nearby rooftops into the underground cistern. This square has been the center of the town since the ninth century. Turn in a slow circle and observe the commotion of rustic-yet-proud facades crowding in a tight huddle around the well. Imagine this square in pilgrimage times, lined by inns and taverns for the town’s guests. Now finger the grooves in the lip of the well and imagine generations of maids and children fetching water. Each Thursday, the square fills with a market—as it has for more than a thousand years.
• Notice San Gimignano’s famous towers.
The Towers: Of the original 72 towers, only 14 survive. Before effective city walls were developed, rich people fortified their own homes with these towers: They provided a handy refuge when ruffians and rival city-states were sacking the town. If under attack, tower owners would set fire to the external wooden staircase, leaving the sole entrance unreachable a story up; inside, fleeing nobles pulled up behind them the ladders that connected each level, leaving invaders no way to reach the stronghold at the tower’s top. These towers became a standard part of medieval skylines. Even after town walls were built, the towers continued to rise—now to fortify noble families feuding within a town (Montague and Capulet-style).
In the 14th century, San Gimignano’s good times turned very bad. In the year 1300, about 13,000 people lived within the walls. Then in 1348, a six-month plague decimated the population, leaving the once-mighty town with barely 4,000 survivors. Once fiercely independent, now crushed and demoralized, San Gimignano came under Florence’s control and was forced to tear down its towers. (The Banca CR Firenze building occupies the remains of one such toppled tower.) And, to add insult to injury, Florence redirected the vital trade route away from San Gimignano. The town never recovered, and poverty left it in a 14th-century architectural time warp. That well-preserved cityscape, ironically, is responsible for the town’s prosperity today.
• From the well, walk 30 yards uphill to the adjoining square with the cathedral.
Piazza del Duomo: The square faces the former cathedral. The twin towers to the right are 10th century, among the first in town. The stubby tower opposite the church is typical of a merchant’s tower: main door on ground floor, warehouse upstairs, holes to hold beams that once supported wooden balconies and exterior staircases, heavy stone on the first floor, cheaper and lighter brick for upper stories.
• On the piazza are the Civic Museum and Tower, worth checking out (see “Sights in San Gimignano,” later). You’ll also see the...
Duomo (or Collegiata): Inside San Gimignano’s Romanesque cathedral, Sienese Gothic art (14th century) lines the nave with parallel themes—Old Testament on the left and New Testament on the right. (For example, from back to front: Creation facing the Annunciation, the birth of Adam facing the Nativity, and the suffering of Job opposite the suffering of Jesus.) This is a classic use of art to teach. Study the fine Creation series (top left). Many scenes are portrayed with a local 14th-century “slice of life” setting, to help lay townspeople relate to Jesus—in the same way that many white Christians are more comfortable thinking of Jesus as Caucasian (€3.50, €5.50 combo-ticket includes mediocre Religious Art Museum—skip it; April-Oct Mon-Fri 10:00-19:10, Sat 10:00-17:10, Sun 12:30-19:10; Nov-March Mon-Sat 10:00-16:40, Sun 12:30-16:40; last entry 20 minutes before closing, buy ticket and enter from the courtyard around the left side).
• From the church, hike uphill (passing the church on your left) following signs to Rocca e Parco di Montestaffoli. Keep walking until you enter a peaceful hilltop park and olive grove within the shell of a 14th-century fortress.
Hilltop Views at the Rocca: On the far side, 33 steps take you to the top of a little tower (free) for the best views of San Gimignano’s skyline; the far end of town and the Sant’Agostino Church (where this walk ends); and a commanding 360-degree view of the Tuscan countryside. San Gimignano is surrounded by olives, grapes, cypress trees, and—in the Middle Ages—lots of wild dangers. Back then, farmers lived inside the walls and were thankful for the protection.
• Return to the bottom of Piazza del Duomo, turn left, and continue your walk across town, cutting under the double arch (from the town’s first wall). In around 1200, this defined the end of town. The Church of San Bartolo stood just outside the wall (on the right). The Maltese cross over the door indicates that it likely served as a hostel for pilgrims. As you continue down Via San Matteo, notice that the crowds have dropped by at least half. Enjoy the breathing room as you pass a fascinating array of stone facades from the 13th and 14th centuries—now a happy cancan of wine shops and galleries. Reaching the gateway at the end of town, follow signs to the right to reach...
Sant’Agostino Church: This tranquil church, at the far end of town (built by the Augustinians who arrived in 1260), has fewer crowds and more soul. Behind the altar, a lovely fresco cycle by Benozzo Gozzoli (who painted the exquisite Chapel of the Magi in the Medici-Riccardi Palace in Florence) tells of the life of St. Augustine, a North African monk who preached simplicity. The kind, English-speaking friars (from Britain and the US) are happy to tell you about their church and way of life, and also have Mass in English on Sundays at 11:00. Pace the peaceful cloister before heading back into the tourist mobs (free, €0.50 lights the frescoes; April-Oct daily 7:00-12:00 & 15:00-19:00; Nov-March Tue-Sun 7:00-12:00 & 15:00-18:00, Mon 16:00-18:00). Their fine little shop, with books on the church and its art, is worth a look.
This small, fun museum, consisting of just three unfurnished rooms and a tower, is inside City Hall (Palazzo Comunale). The main room (across from the ticket desk), called the Sala di Consiglio (a.k.a. Dante Hall), is covered in festive frescoes, including the Maestà by Lippo Memmi. This virtual copy of Simone Martini’s Maestà in Siena proves that Memmi didn’t have quite the same talent as his famous brother-in-law.
Upstairs, the Pinacoteca displays a classy little painting collection of mostly altarpieces. The highlight is a 1422 altarpiece by Taddeo di Bartolo honoring St. Gimignano (far end of last room). You can see the saint, with the town—bristling with towers—in his hands, surrounded by events from his life.
Before going back downstairs, be sure to stop by the Mayor’s Room (Camera del Podestà, across the stairwell from the Pinacoteca). Frescoed in 1310 by Memmo di Filippuccio, it offers an intimate and candid peek into the 14th century. The theme: profane love. As you enter, look to the left corner where a young man is ready to experience the world. He hits his parents up for a bag of money and is free. On the opposite wall (above the window), you’ll see a series of bad decisions: Almost immediately he’s entrapped by two prostitutes, who lead him into a tent where he loses his money, is turned out, and is beaten. Above the door, from left to right, you see a parade of better choices: marriage, the cradle of love, the bride led to the groom’s house, and newlyweds bathing together and retiring happily to their bed.
The highlight for most visitors is a chance to climb the Tower (Torre Grossa, entrance halfway down the stairs from the Pinacoteca). The city’s tallest tower, 200 feet and 218 steps up, rewards those who climb it with a commanding view. See if you can count the town’s 14 towers (yes, that includes the stubby little one just below this tower). It’s a sturdy, modern staircase most of the way, but the last stretch is a steep, ladder-like climb.
Coming back down to earth, you leave the complex via a delightful stony loggia and courtyard out back.
Cost and Hours: €5 includes museum and tower, daily April-Sept 9:30-19:00, Oct-March 11:00-17:30, Piazza del Duomo, tel. 0577-990-312.
This small but interesting attraction, located inside the Palazzo Ficarelli on a quiet street a block over from the main street, is a trip back in time. When possible, attendants like to lead visitors on individual tours around the small exhibit. The highlight is a painstakingly rendered 1:100 scale clay model of San Gimignano at the turn of the 14th century. You can see the 72 original “tower houses,” and marvel at how unchanged the street plan remains today. You’ll peek into cross-sections of buildings, view scenes of medieval life both within and outside the city walls, and watch videos about town history and the making of the model. After walking through a gallery of modern Italian sculpture, your visit ends in the ceramics workshop next door, where models like this one are created from wet lumps of clay. (Conveniently, the “workshop” is one corner of a ceramics shop.) While cynics might view this as little more than a gimmick to sell more little ceramic buildings, the detail of the model is truly enchanting.
Cost and Hours: €5; April-Oct daily 10:00-19:00; Nov-March Mon-Fri 10:00-17:00, Sat-Sun until 18:00; Via Berignano 23, tel. 0577-941-078, www.sangimignano1300.com.
Although the town is a zoo during the daytime, locals outnumber tourists when evening comes, and San Gimignano becomes mellow and enjoyable. Drivers can unload near their hotels, then park outside the walls in recommended lots. Hotel websites provide instructions.
$$$ Hotel l’Antico Pozzo is an elegantly restored, 15th-century townhouse with 18 tranquil, comfortable rooms, a peaceful interior courtyard terrace, and an elite air (Sb-€95, small Db-€120, standard Db-€140, big Db-€180, includes breakfast, air-con, elevator, free Wi-Fi, near Porta San Matteo at Via San Matteo 87, tel. 0577-942-014, www.anticopozzo.com, info@anticopozzo.com; Emanuele, Elisabetta, and Mariangela). If arriving by bus, save a crosstown walk by asking for the Porta San Matteo stop (rather than getting off at the main stop near Porta San Giovanni).
$$$ Hotel la Cisterna, right on Piazza della Cisterna, feels old and stately, with 49 predictable rooms, some with panoramic view terraces—a scene from the film Tea with Mussolini was filmed from one (Sb-€78, Db-€100, Db with view-€125, Db with view terrace—€140, 10 percent discount with this book when you book direct, includes buffet breakfast, air-con, elevator, free Wi-Fi, good restaurant with great view, closed Jan-Feb, Piazza della Cisterna 23, tel. 0577-940-328, www.hotelcisterna.it, info@hotelcisterna.it, Alessio).
$$$ Ponte a Nappo, run by enterprising Carla Rossi (who doesn’t speak English) and her sons Francesco and Andrea (who do), has seven comfortable rooms and two apartments in a kid-friendly farmhouse. Located a long half-mile below town (best for drivers, but doable for hardy walkers), this place has killer views. A picnic dinner lounging on their comfy garden furniture as the sun sets is good Tuscan living (Db-€100-130, 2- to 6-person apartment-€130-250, price depends on season and length of stay, for best price book direct and mention Rick Steves, air-con mid-June-mid-Sept only, free Wi-Fi, free parking, pool, free loaner bikes, lunch and dinner sometimes available to guests, 15-minute walk or 5-minute drive from Porta San Giovanni, tel. 0577-907-282, mobile 349-882-1565, www.accommodation-sangimignano.com, info@rossicarla.it). About 100 yards below the monument square at Porta San Giovanni, find Via Vecchia (not left or right, but down a tiny road) and follow it down a dirt road for five minutes by car. They also rent a dozen or so rooms and apartments in town (including some in the Palazzo Tortoli, a stone tower right on the main square, Db-€75-110, pay Wi-Fi, each room is described on their website).
$$ Palazzo al Torrione, on an untrampled side street just inside Porta San Giovanni, is quiet and handy, and generally better than most hotels (even though they don’t have a full-time reception). Their 10 modern rooms are spacious and tastefully appointed (Db-€90, terrace Db-€110, Tb-€100, terrace Tb-€120, Qb-€120-130, 10 percent discount with this book when you book direct, breakfast-€7, communal kitchen with Wi-Fi, parking-€6/day, inside and left of gate at Via Berignano 76; operated from tobacco shop 2 blocks away, on the main drag at Via San Giovanni 59; tel. 0577-940-480, mobile 338-938-1656, www.palazzoaltorrione.com, palazzoaltorrione@palazzoaltorrione.com, Vanna and Francesco).
$ Le Vecchie Mura Camere offers three good rooms above their restaurant in the old town (Db-€65, no breakfast, air-con, free Wi-Fi, Via Piandornella 15, tel. 0577-940-270, www.vecchiemura.it, info@vecchiemura.it, Bagnai family).
$ Locanda il Pino has just seven rooms and a big living room. It’s dank but clean and quiet. Run by English-speaking Elena and her family, it sits above their elegant restaurant just inside Porta San Matteo (Db-€55, no breakfast, free Wi-Fi in lobby, easy parking just outside the gate, Via Cellolese 4, tel. 0577-940-415, locanda@ristoranteilpino.it). If you’re arriving by bus, ask for the Porta San Matteo stop, rather than the main stop near Porta San Giovanni.
My first two listings cling to quiet, rustic lanes overlooking the Tuscan hills (yet just a few steps off the main street); the rest are buried deep in the old center.
Dulcis in Fundo Ristorante, small and family-run, proudly serves modest portions of “revisited” Tuscan cuisine (with a modern twist and gourmet presentation) in a jazzy ambience. This enlightened place, whose menu identifies the sources of their ingredients, offers lots of vegetarian options and gladly caters to gluten-free diets—rare in Tuscany (€12 pastas, €13-16 secondi, meals served 12:30-14:30 & 19:15-21:30, closed Wed, Vicolo degli Innocenti 21, tel. 0577-941-919, Roberto and Cristina).
Le Vecchie Mura Ristorante has good and fast service, great prices, tasty if unexceptional home cooking, and the ultimate view. It’s romantic indoors or out. They have a dressy, modern interior where you can dine with a view of the busy stainless-steel kitchen under rustic vaults, but the main reason to come is for the incredible cliffside garden terrace. Cliffside tables are worth reserving in advance by calling or dropping by: Ask for “front view” (€8-11 pastas, €12-15 secondi, open only for dinner from 18:00, last order at 22:00, closed Tue, Via Piandornella 15, tel. 0577-940-270, Bagnai family).
Cum Quibus (“In Company”), tucked away near Porta San Matteo, has a smallish dining room with soft music, beamed ceilings, and modern touches; it also offers al fresco tables in its interior patio in summer. Lorenzo and Fabiana produce tasty Tuscan cuisine, fresh truffle specialties, and artistic desserts (€10 pastas, €15 secondi, truffle dishes more expensive, Wed-Mon 12:30-14:30 & 19:00-22:00, closed Tue, reservations advised, Via San Martino 17, tel. 0577-943-199, www.cumquibus.it).
Trattoria Chiribiri, just inside Porta San Giovanni on the left, serves homemade pastas and desserts at remarkably fair prices. While its petite size and tight seating make it hot in the summer, it’s a good budget option—and as such, it’s in all the guidebooks (€8 pastas, €10 secondi, daily 11:00-23:00, Piazza della Madonna 1, tel. 0577-941-948, Maria and Maurizio).
Locanda di Sant’Agostino spills out onto the peaceful square, facing Sant’Agostino Church. It’s cheap and cheery, serving lunch and dinner daily—big portions of basic food in a restful setting. Dripping with wheat stalks and atmosphere on the inside, there’s shady on-the-square seating outside (€8 pizzas, pastas, and bruschette; €9-15 secondi, daily 11:00-22:00, closed Tue off-season and Jan-Feb, Piazza Sant’Agostino 15, tel. 0577-943-141, Genziana and sons).
Enoteca: diVinorum, a cool wine bar with a small entrance right on Piazza Cisterna, has a contemporary cellar atmosphere and—best of all—a row of tables out back overlooking rolling Tuscan hills (just downhill and toward the main drag from Dulcis in Fundo, recommended above; at mealtimes, you’ll have to order food to sit at the outdoor tables). They have local wines by the glass (€3-5) as well as snacks that can easily make a light meal (€10-15 antipasti plates, €7-8 bruschette and warm plates, daily 11:00-21:30, Nov-April until 20:00, Piazza Cisterna 30 or Via degli Innocenti 5, tel. 0577-907-192, Matteo).
Picnics: The big, modern Co-op supermarket sells all you need for a nice spread (Mon-Sat 8:30-20:00, Sun 8:30-12:30 except closed Sun Nov-March, at parking lot below Porta San Giovanni). Or browse the little shops guarded by boar heads within the town walls; they sell pricey boar meat (cinghiale). Pick up 100 grams (about a quarter pound) of boar, cheese, bread, and wine and enjoy a picnic in the garden at the Rocca or the park outside Porta San Giovanni.
Gelato: To cap the evening and sweeten your late-night city stroll, stop by Gelateria Dondoli on Piazza della Cisterna (at #4). Gelato-maker Sergio was a member of the Italian team that won the official Gelato World Cup—and his gelato really is a cut above (daily 8:00-24:00, closes at 19:00 off-season, tel. 0577-942-244, Dondoli family).
Bus tickets are sold at the bar just inside the town gate or at the TI. Many connections require a change at Poggibonsi (poh-jee-BOHN-see, with a soft “g”), which is also the nearest train station.
From San Gimignano by Bus to: Florence (hourly, less on Sun, 1.5-2 hours, change in Poggibonsi, €6.80), Siena (8/day direct, on Sun must change in Poggibonsi, 1.25 hours, €6), Volterra (4/day Mon-Sat; on Sun only 1/day—in the late afternoon and usually crowded—with no return to San Gimignano; 2 hours, change in Colle Val d’Elsa, €6.15). Note that the bus connection to Volterra is four times as long as the drive; if you’re desperate to get there faster, you can pay about €70 for a taxi.
By Car: San Gimignano is an easy 45-minute drive from Florence (take the A-1 exit marked Firenze Certosa, then a right past tollbooth following Siena per 4 corsie sign; exit the freeway at Poggibonsi). From San Gimignano, it’s a scenic and windy half-hour drive to Volterra.
Encircled by impressive walls and topped with a grand fortress, Volterra sits high above the rich farmland surrounding it. More than 2,000 years ago, Volterra was one of the most important Etruscan cities, and much larger than we see today. Greek-trained Etruscan artists worked here, leaving a significant stash of art, particularly funerary urns. Eventually Volterra was absorbed into the Roman Empire, and for centuries it was an independent city-state. Volterra fought bitterly against the Florentines, but like many Tuscan towns, it lost in the end and was given a fortress atop the city to “protect” its citizens.
Unlike other famous towns in Tuscany, Volterra feels neither cutesy nor touristy...but real, vibrant, and almost oblivious to the allure of the tourist dollar. This probably stems from the Volterrans’ feisty resistance to change. (At a recent town meeting about whether to run high-speed Internet cable to the town, a local grumbled, “The Etruscans didn’t need it—why do we?”) This stubbornness helps make Volterra a refreshing change of pace from its more commercial neighbors. It also boasts some particularly fine sights for a small town, from a remarkably intact ancient Roman theater, to a finely decorated Pisan Romanesque cathedral, to an excellent museum of Etruscan artifacts. All in all, Volterra is my favorite small town in Tuscany.
Compact and walkable, the city stretches out from the pleasant Piazza dei Priori to the old city gates.
The helpful TI is on the main square, at Piazza dei Priori 19 (daily 9:00-13:00 & 14:00-18:00, tel. 0588-87257, www.volterratur.it). The TI’s excellent €5 audioguide narrates 20 stops (2-for-1 discount on audioguides with this book).
By Public Transport: Buses stop at Piazza Martiri della Libertà in the town center. Train travelers can reach the town with a short bus ride (see “Volterra Connections,” later.)
By Car: Drivers will find the town ringed with easy numbered parking lots (#5, #6, and #8 are free; #3 is for locals only). The most central lots are the pay lots at Porta Fiorentina and underground at Piazza Martiri della Libertà (€1.50/hour, €11/24 hours).
Market Day: The market is on Saturday morning near the Roman Theater (8:00-13:00, at parking lot #5; in winter, it’s right on Piazza dei Priori). The TI hands out a list of other market days in the area.
Festivals: Volterra’s Medieval Festival takes place the third and fourth Sundays of August. Fall is a popular time for food festivals—check with the TI for dates and events planned.
Internet Access: Web & Wine has a few terminals, fine wine by the glass, and organic vegetarian food (€3/hour, no minimum, summer daily 9:30-1:00 in the morning, closed Thu in Sept-May, Via Porta all’Arco 11-15, tel. 0588-81531, Lallo speaks English). Enjoy Café Internet Point has a couple of terminals in their basement (€3/hour, daily 6:30-1:00 in the morning, Piazza dei Martiri 3, tel. 0588-80530).
Laundry: The handy self-service Lavanderia Azzurra is just off the main square (€4 wash, €4 dry, daily 7:00-23:00, Via Roma 7, tel. 0588-80030).
Annie Adair (also listed individually, next) and her colleagues offer a great one-hour, English-only introductory walking tour of Volterra for €10. The walk touches on Volterra’s Etruscan, Roman, and medieval history, as well as the contemporary cultural scene (April-July and Sept-Oct daily, rain or shine, at 18:00; meet in front of alabaster shop on Piazza Martiri della Libertà, no need to reserve—just show up, they need a minimum of 3 people, or €30—to make the tour go, www.volterrawalkingtour.com or www.tuscantour.com, info@volterrawalkingtour.com). There’s no better way to spend €10 and one hour in this city.
American Annie Adair is an excellent city guide. She and her husband Francesco, a sommelier, organize private history and wine tours and even Tuscan weddings for Americans (€50/hour, minimum 2 hours, tel. 0588-086-201, mobile 347-143-5004, www.tuscantour.com, info@tuscantour.com). Francesco leads a one-hour “Wine Tasting 101” crash course in sampling Tuscan wines, held at a local wine bar (€50 per group plus cost of wine).
▲Etruscan Arch (Porta all’Arco)
“Artisan Lane”(Via Porta all’Arco)
Pinacoteca and Alabaster Museum
▲▲Etruscan Museum (Museo Etrusco Guarnacci)
▲La Vena di Vino (Wine-Tasting with Bruno and Lucio)
Medici Fortress and Archaeological Park
I’ve arranged these sights as a handy little town walk, connected by directions on foot. Not all the sights will interest everyone, so skim the listings to decide which detours appeal to you.
• Begin your visit of town at the Etruscan Arch. To find it, go all the way down to the bottom of Via Porta all’Arco (you’ll find the top of this street between Piazza Martiri della Libertà, with the town bus stop, and the main square, Piazza dei Priori).
Volterra’s most famous sight is its Etruscan arch, built of massive, volcanic tuff stones in the fourth century B.C. (for more information on tuff, see the sidebar on here). Volterra’s original wall was four miles around—twice the size of the wall that encircles it today. With 25,000 people, Volterra was a key trading center and one of 12 leading towns in the confederation of Etruria Propria. The three seriously eroded heads, dating from the first century B.C., show what happens when you leave something outside for 2,000 years. The newer stones are part of the 13th-century city wall, which incorporated parts of the much older Etruscan wall.
A plaque just outside remembers June 30, 1944. That night, Nazi forces were planning to blow up the arch to slow the Allied advance. To save their treasured landmark, Volterrans ripped up the stones that pave Via Porta all’Arco and plugged the gate, managing to convince the Nazi commander that there was no need to blow up the arch. Today, all the stones are back in their places, and like silent heroes, they welcome you through the oldest standing Etruscan gate into Volterra. Locals claim this as the only surviving round arch of the Etruscan age; most experts believe this is where the Romans got the idea for using a keystone in their arches.
• Go through the arch and head up Via Porta all’Arco, which I like to call...
This steep and atmospheric strip is lined with interesting shops featuring the work of artisans and producers. Because of its alabaster heritage, Volterra attracted craftsmen and artists, who brought with them a rich variety of handiwork (shops generally open Mon-Sat 10:00-13:00 & 16:00-19:00, closed Sun; the TI produces a free booklet called Handicraft in Volterra).
From the Etruscan Arch, browse your way up the hill, checking out these shops and items (listed from bottom to top): La Mia Fattoria—a co-op of producers of cheese, salami, and olive oil lets you buy direct at farm prices (just up Via Laberinti near #52); alabaster shops (#57, #50, and #45); book bindery and papery (#26); jewelry (#25); etchings (#23); Web & Wine (Internet access; #11-15); and bronze work (#6).
• Reaching the top of Via Porta all’Arco, turn left and walk a few steps into Volterra’s main square, Piazza dei Priori. It’s dominated by the...
Volterra’s City Hall (c. 1209) claims to be the oldest of any Tuscan city-state. It clearly inspired the more famous Palazzo Vecchio in Florence. Town halls like this are emblematic of an era when city-states were powerful. They were architectural exclamation points declaring that, around here, no pope or emperor called the shots. Towns such as Volterra were truly city-states—proudly independent and relatively democratic. They had their own armies, taxes, and even weights and measures. Notice the horizontal “cane” cut into the City Hall wall (right of the door). For a thousand years, this square hosted a market, and the “cane” was the local yardstick. When not in use for meetings or weddings, the city council chambers—lavishly painted and lit with fun dragon lamps, as they have been for centuries of town meetings—are open to visitors.
The tower was recently opened to the public. For the adventurous, 70 or so steps take you up a tight, winding, metal staircase to a small platform with great panoramic views of the city and surrounding countryside. Be aware that this is the bell tower; expect loud chimes if you visit on the hour or half-hour.
Cost and Hours: €1.50, €2.00 additional for tower, mid-March-Oct daily 10:30-17:30, Nov-mid-March Sat-Sun only 10:00-17:00.
• Facing the City Hall, notice the black-and-white-striped wall to the right (set back from the square). The door in that wall leads into Volterra’s...
Tuff (tufo in Italian) is a light-colored volcanic rock that is common in Italy. A part of Tuscany is even called the “Tuff Area.” The seven hills of Rome are made of tuff, and quarried blocks of this stone can be seen in the Colosseum, Pantheon, and Castel Sant’Angelo. Just outside of Rome, the catacombs were carved from tuff. Sorrento rises above the sea on a tuff outcrop. Orvieto, Civita di Bagnoregio (pictured), and many other hill towns perch on bluffs of tuff.
Italy’s early inhabitants, including the Etruscans and Romans, carved caves, tunnels, burial niches, and even roads out of tuff. Blocks of this rock were quarried to make houses and walls. Tuff is soft and easy to carve when it’s first exposed to air, but hardens later, which makes it a good building stone.
Italy’s tuff-producing volcanoes resulted from a lot of tectonic-plate bumping and grinding. This violent geologic history is reflected in Italy’s volcanoes, like Vesuvius and Etna, and earthquakes such as the 2009 quake in the L’Aquila area northeast of Rome.
Tuff is actually just a big hardened pile of old volcanic ash. When volcanoes hold magma that contains a lot of water, they erupt explosively (think heat + water = steam = POW!). The exploded rock material gets blasted out as hot volcanic ash, which settles on the surrounding landscape, piles up, and over time welds together into the rock called tuff.
So when you’re visiting an area in Italy of ancient caves or catacombs built out of this material, you’ll know that at least once (and maybe more) upon a time, it was a site of a lot of volcanic activity.
This church is not as elaborate as its cousin in Pisa, but the simple 13th-century facade and the interior (rebuilt in the late 16th century), with its central nave flanked by monolithic stone columns, are beautiful examples of the Pisan Romanesque style.
Cost and Hours: Free, daily 8:00-12:30 & 15:00-18:00, Nov-March until 17:00, closed Fri 15:00-16:00 while the cleaners religiously perform their duties.
Visiting the Church: Enter through the door off Piazza dei Priori (technically the back door), and take a moment to let your eyes adjust to this dark, Romanesque space. (If you come through the main door around on Piazza San Giovanni, do this tour in reverse.) The interior was decorated mostly in the late 16th century, during Florentine rule under the Medici family. Their coat of arms, with its distinctive balls (called palle), is repeated multiple times throughout the building.
Head down into the nave to face the main altar. Up the stairs just to the right is a dreamy painted and gilded-wood Deposition (Jesus being taken down from the cross), restored to its original form. Carved in 1228, a generation before Giotto, it shows emotion and motion way ahead of its time (€1 buys some light).
The glowing windows in the transept and behind the altar are sheets of alabaster. These, along with the recorded Gregorian chants, add to the church’s wonderful ambience.
The 12th-century marble pulpit is also beautifully carved. In the relief panel of the Last Supper, all the apostles are together except Judas, who’s under the table with the evil dragon (his name is the only one not carved into the relief).
Just past the pulpit on the right (at the Rosary Chapel), check out the Annunciation by Fra Bartolomeo (who was a student of Fra Angelico and painted this in 1497). Bartolomeo delicately gives worshippers a way to see Mary “conceived by the Holy Spirit.” Note the vibrant colors, exaggerated perspective, and Mary’s contrapposto pose—all attributes of the Renaissance.
At the end of the nave, the chapel to the right of the doors has painted terra-cotta statue groups of the Nativity and the Adoration of the Magi, thought to be the work of master ceramists Luca and Andrea della Robbia. Luca is credited with inventing the glazing formula that makes his inventive sculptures shine even in poorly lit interiors.
To see a classically Pisan space, step outside the door into Piazza San Giovanni. A common arrangement in the Middle Ages was for the church to face the baptistery (you couldn’t enter the church until you were baptized)...and for the hospital to face the cemetery (now the site of the local ambulance corps). These buildings all overlooked the same square. That’s how it is in Pisa, and that’s how it is here.
• Exit the cathedral out the back door into the main square, Piazza dei Priori. Face the City Hall, and go down the street to the left; after one short block, you’re standing at the head (on the left) of...
The town’s main drag, named after the popular Socialist leader Giacomo Matteotti (killed by the Fascists in 1924), provides a good cultural scavenger hunt.
At #1 is a typical Italian bank security door. (Step in and say, “Beam me up, Scotty.”) Back outside, stand at the corner, and look up and all around. Find the medieval griffin torch holder—symbol of Volterra—and imagine it holding a lit torch. The pharmacy sports the symbol of its medieval guild. Across the street from the bank, #2 is the base of what was a San Gimignano-style fortified Tuscan tower. Look up and imagine heavy beams cantilevered out, supporting extra wooden rooms and balconies crowding out over the street. Throughout Tuscany, today’s stark and stony old building fronts once supported a tangle of wooden extensions.
As you head down Via Matteotti, notice how the doors show centuries of refitting work. Doors that once led to these extra rooms are now partially bricked up to make windows. Contemplate urban density in the 14th century, before the plague thinned out the population. Be careful: There’s a wild boar (a local delicacy) at #10.
At #12, notice the line of doorbells: This typical palace, once the home of a single rich family, is now occupied by many middle-class families. After the social revolution in the 18th century and the rise of the middle class, former palaces were condominium-ized. Even so, like in Dr. Zhivago, the original family still lives here. Apartment #1 is the home of Count Guidi.
At #16, pop in to an alabaster showroom. Alabaster, mined nearby, has long been a big industry here. Volterra alabaster—softer and more porous than marble—was sliced thin to serve as windows for Italy’s medieval churches.
At #19, the recommended La Vecchia Lira is a lively cafeteria. The Bar L’Incontro across the street is a favorite for pastries; in the summer, they sell homemade gelato, while in the winter they make chocolates.
Across the way, up Vicolo delle Prigioni, is a fun bakery (panificio). They’re happy to sell small quantities if you want to try the local cantuccini (almond biscotti) or another treat (closed 14:00-17:30, Sat after 14:00, and all day Sun).
Continue to the end of the block. At #51, a bit of Etruscan wall is artfully used to display more alabaster art. And #56A is the alabaster art gallery of Paolo Sabatini.
Locals gather early each evening at Osteria dei Poeti (at #57) for some of the best cocktails in town—served with free munchies. The cinema is across the street. Movies in Italy are rarely in versione originale; Italians are used to getting their movies dubbed into Italian. To bring some culture to this little town, they also show live transmissions of operas and concerts (advertised in the window).
At #66, another Tuscan tower marks the end of the street. This noble house has a ground floor with no interior access to the safe upper floors. Rope ladders were used to get upstairs. The tiny door was wide enough to let in your skinny friends...but definitely not anyone wearing armor and carrying big weapons.
Across the street stands the ancient Church of St. Michael. After long years of barbarian chaos, the Lombards moved in from the north and asserted law and order in places like Volterra. That generally included building a Christian church on the old Roman forum to symbolically claim and tame the center of town. (Locals still call this San Michele in Foro—“in the forum.”) The church standing here today is Romanesque, dating from the 12th century. Around the right side, find the crude little guy and the smiling octopus under its eaves—they’ve been making faces at the passing crowds for 800 years.
• Three more sights—Palazzo Viti (fancy old palace), the Pinacoteca (gallery of gilded altarpieces), and the Alabaster Museum (within the Pinacoteca building)—are a short stroll down Via dei Sarti: From the end of Via Matteotti, turn left. If you want to skip straight down to the Roman Theater, just head straight from the end of Via Matteotti onto Via Guarnacci, then turn left when you get to the Porta Fiorentina gate. To head directly to Volterra’s top sight, the Etruscan Museum, just turn around, walk a block back up Via Matteotti, turn left on Via Gramsci, and follow it all the way through Piazza XX Settembre up Via Don Minzoni to the museum.
Go behind the rustic, heavy stone walls of the city and see how the nobility lived (in this case, rich from 19th-century alabaster wealth). One of the finest private residential buildings in Italy, with 12 rooms open to the public, Palazzo Viti feels remarkably lived in—because it is. You’ll also find Signora Viti herself selling admission tickets. It’s no wonder this time warp is so popular with Italian movie directors. Remember, you’re helping keep a noble family in leotards.
Cost and Hours: €5, pick up the loaner English description, April-Oct daily 10:00-13:00 & 14:30-18:30, closed Nov-March, Via dei Sarti 41, tel. 0588-84047, www.palazzoviti.it.
• A block past Palazzo Viti, also on Via dei Sarti, is the...
The Pinacoteca fills a 15th-century palace with fine paintings that feel more Florentine than Sienese—a reminder of whose domain this town was in. You’ll see roomfuls of gilded altarpieces and saintly statues. Head upstairs to the first floor. If you go left, you’ll circle all the way around and save the best for last—but to cut to the chase, turn right at the landing and go directly into the best room, with Luca Signorelli’s beautifully lit Annunciation (1491), an example of classic High Renaissance (from the town cathedral), and (to the right) Deposition from the Cross (1521), the groundbreaking Mannerist work by Rosso Fiorentino (note the elongated bodies and harsh emotional lighting and colors). In the adjacent room, see Ghirlandaio’s Christ in Glory (1492). The two devout-looking kneeling women are actually pagan, pre-Christian Etruscan demigoddesses, Attinea and Greciniana, but the church identified them as obscure saints to make the painting acceptable. Rather than attempt to get locals to stop venerating them (as their images were all over town), the church simply sainted them. Upstairs, the second floor has three more rooms of similar art.
A new staircase leads down to the recently opened Alabaster Museum. With alabaster sculptures spread over four floors, the museum contains examples from Etruscan times until the present (and lacked English descriptions when I visited). The top floor shows tools used to work the stone. Etruscan pieces are on the third floor, and modern sculptures—including an intriguing alabaster fried egg—are on the lower floors. As you leave, note the fine, tranquil, cloister-like courtyard with the remains of its original well.
Cost and Hours: €6 for Pinacoteca, €8 for Alabaster, €10 combo-ticket covers both museums plus Etruscan Museum, daily 9:00-18:45, Nov-mid-March until 13:45, Via dei Sarti 1, no photos permitted, tel. 0588-87580.
• Exiting the Pinacoteca, turn right, then right again down the Passo del Gualduccio passage into the parking-lot square; at the end of this square, turn right and walk along the wall, with fine views of the...
Built in about 40 B.C., this well-preserved theater has good acoustics. Because a fine aerial view is available from the city wall promenade, you may find it unnecessary to pay admission to enter. Belly up to the 13th-century wall and look down. The wall that you’re standing on divided the theater from the town center...so, naturally, the theater became the town dump. Over time, the theater was forgotten—covered in the garbage of Volterra. Luckily, it was rediscovered in the 1950s, by an administrator (and armchair historian) at the local mental hospital. Since they couldn’t secure government funding for the dig, the theater was first excavated by mental patients who found the activity therapeutic.
The stage wall was standard Roman design—with three levels from which actors would appear: one level for mortals, one for heroes, and the top one for gods. Parts of two levels still stand. Gods leaped out onto the third level for the last time around the third century A.D., which is when the town began to use the theater stones to build fancy baths instead. You can see the remains of the baths behind the theater, including the round sauna with brick supports that raise the heated floor.
From the vantage point on the city wall promenade, you can trace Volterra’s vast Etruscan wall. Find the church in the distance, on the left, and notice the stones just below. They are from the Etruscan wall that followed the ridge into the valley and defined Volterra in the fourth century B.C.
Cost and Hours: €3.50, but you can view the theater free from Via Lungo le Mure; the entrance is near the little parking lot just outside Porta Fiorentina—you can see the entry to the right as you survey the theater from above; mid-March-Oct daily 10:30-17:30, Nov-mid-March Sat-Sun only 10:00-16:00, may be closed in bad weather.
• From the Roman Theater, make your way back to Via Matteotti (follow Via Guarnacci straight up from Porta Fiorentina). A block down Via Matteotti, you can’t miss the wide, pedestrianized shopping street called Via Gramsci. Follow this up to Piazza XX Settembre, walk through that leafy square, and continue uphill on Via Don Minzoni. Watch on your left for the...
Filled top to bottom with rare Etruscan artifacts, this museum—even with few English explanations and its dusty, almost neglectful, old-school style—makes it easy to appreciate how advanced this pre-Roman culture was.
Cost and Hours: €8, €10 combo-ticket includes the Pinacoteca and Alabaster Museum; daily mid-March-Oct 9:00-19:00, Nov-mid-March 10:00-16:00; ask at the ticket window for mildly interesting English pamphlet, audioguide-€3, Via Don Minzoni 15, tel. 0588-86347, www.comune.volterra.pi.it/english.
Visiting the Museum: The museum’s three floors feel dusty and disorganized. As there are scarcely any English explanations, consider the serious but interesting €3 audioguide; the information below hits the highlights.
Ground Floor: The collection starts with a small gathering of pre-Etruscan Villanovian artifacts (c. 1500 B.C., to the left as you enter), but its highlight is straight ahead, sprawling through several rooms: a seemingly endless collection of Etruscan funerary urns (dating from the seventh to the first century B.C.). Designed to contain the ashes of cremated loved ones, each urn is tenderly carved with a unique scene, offering a peek into the still-mysterious Etruscan society. Etruscan urns have two parts: The casket on the bottom contained the remains (with elaborately carved panels), while the lid was decorated with a sculpture of the departed.
First pay attention to the people on top. While contemporaries of the Greeks, the Etruscans were more libertine. Their religion was less demanding, and their women were a respected part of both the social and public spheres. Women and men alike are depicted lounging on Etruscan urns. While they seem to be just hanging out, the lounging dead were actually offering the gods a banquet—in order to gain their favor in the transition to the next life. The banquet—where Etruscans really did lounge like this in front of a table—was the epitome of their social structure. But the outcome of this particular banquet had eternal consequences. The dearly departed are often depicted holding scrolls, blank wax tablets (symbolizing blank new lives in the next world), and containers that would generally be used at banquets, including libation cups for offering wine to the gods. The women in particular are finely dressed, sometimes holding a pomegranate (symbolizing fertility) or a mirror. Look at the faces, and imagine the lives they lived and the loved ones they left behind.
Around 550 B.C.—just before the Golden Age of Greece—the Etruscan people of central Italy had their own Golden Age. Though their origins are mysterious, their mix of Greek-style art with Roman-style customs helped lay a civilized foundation for the rise of the Roman Empire. As you travel through Italy—particularly in Tuscany (from “Etruscan”), you’ll find traces of this long-lost people.
Etruscan tombs and artifacts are still being discovered, often by farmers in the countryside. Museums in Volterra and Cortona house fine collections of urns, pottery, and devotional figures. You can visit several domed tombs outside Cortona.
The Etruscans first appeared in the ninth century B.C., when a number of cities sprouted up in sparsely populated Tuscany and Umbria, including today’s hill towns of Cortona, Chiusi, and Volterra. Possibly immigrants from Turkey, but more likely local farmers who moved to the city, they became traders and craftsmen, and welcomed new ideas from Greece.
More technologically advanced than their neighbors, the Etruscans mined metal, exporting it around the Mediterranean, both as crude ingots and as some of the finest-crafted jewelry in the known world. They drained and irrigated large tracts of land, creating the fertile farmland of central Italy’s breadbasket. With their disciplined army, warships, merchant vessels, and (from the Greek perspective) pirate galleys, they ruled central Italy and the major ports along the Tyrrhenian Sea. For nearly two centuries (c. 700-500 B.C.), much of Italy lived a Golden Age of peace and prosperity under the Etruscan sun.
Judging from the frescoes and many luxury items that have survived, the Etruscans enjoyed the good life: They look healthy and vibrant as they play flutes, dance with birds, or play party games. Etruscan artists celebrated individual people, showing their wrinkles, crooked noses, silly smiles, and funny haircuts.
Thousands of surviving ceramic plates and cups attest to the importance of food. Men and women ate together, propped on their elbows on dining couches, surrounded by colorful decor. According to contemporary accounts, the Etruscans, even their slaves, were Europe’s best-dressed people. The banqueters were entertained with music and dancing, and served by elegant and well-treated slaves.
Scholars today have deciphered the Etruscans’ Greek-style alphabet and some individual words, but they have yet to fully crack the code. Much of what we know of the Etruscans comes from their tombs. The tomb was a home in the hereafter, complete with all of the deceased’s belongings. The sarcophagus might have a statue on the lid of the deceased at a banquet—lying across a dining couch, spooning with his wife, smiles on their faces, living the good life for all eternity.
Seven decades of wars with the Greeks (545-474 B.C.) disrupted their trade routes and drained the Etruscan League, just as a new Mediterranean power was emerging: Rome. In 509 B.C., the Romans overthrew their Etruscan king, and Rome expanded, capturing Etruscan cities one by one (the last in 264 B.C.). Etruscan resisters were killed, the survivors intermarried with Romans, and their kids grew up speaking Latin. By Julius Caesar’s time, the only remnants of Etruscan culture were its priests, who became Rome’s professional soothsayers. Interestingly, the Etruscan prophets had foreseen their own demise, having predicted that Etruscan civilization would last 10 centuries.
But Etruscan culture lived on in Roman religion (pantheon of gods, household gods, and divination rituals), art (realism), lifestyle (the banquet), and in a taste for Greek styles—the mix that became our “Western civilization.”
Now tune into the reliefs carved into the fronts of the caskets. The motifs vary widely, from floral patterns to mystical animals (such as a Starbucks-like mermaid) to parades of magistrates. Most show journeys on horseback—appropriate for someone leaving this world and entering the next. The most evocative scenes show the fabled horseback-and-carriage ride to the underworld, where the dead are greeted by Charon, an underworld demon, with his hammer and pointy ears.
While the finer urns are carved of alabaster, most are made of limestone. Originally they were colorfully painted. Many lids are mismatched—casualties of reckless 18th- and 19th-century archaeological digs.
First Floor: You’ll enter a room with a circular mosaic in the floor (a Roman original, found in Volterra and transplanted here). Turn left into a series of green rooms—the best presented (and most important) of the museum.
The first room, Sala XIV, collects scenes of Ulysses carved into the fronts of caskets. Turn left and head into Sala XV, with the museum’s prize piece. Fans of Alberto Giacometti will be amazed at how the tall, skinny figure called The Evening Shadow (L’Ombra della Sera, third century B.C.) looks just like the modern Swiss sculptor’s work—but is 2,500 years older. This is an exceptional example of the ex-voto bronze statues that the Etruscans created in thanks to the gods. With his supremely lanky frame, distinctive wavy hairdo, and inscrutable Mona Lisa smirk, this Etruscan lad captures the illusion of a shadow stretching long late in the day. Admire the sheer artistry of the statue; with its right foot shifted slightly forward, it even hints at the contrapposto pose that would become common in this same region during the Renaissance, two millennia later.
Continue circling clockwise, through Sala XVI (alabaster urns with more Greek myths), Sala XVII (ex-voto water-bearer statues, kraters—vases with handles, and bronze hand mirrors), and Sala XVIII (golden jewelry). Sala XIX shows off the museum’s other top piece, the Urn of the Spouses (Urna degli Sposi, first century B.C.). It’s unique for various reasons, including its material (it’s in terra-cotta—a relatively rare material for these funerary urns) and its depiction of two people rather than one. Looking at this elderly couple, it’s easy to imagine the long life they spent together and their desire to pass eternity lounging with each other at a banquet for the gods.
The rest of this floor has black glazed pottery; thousands of Etruscan, Greek, and Roman coins; and many more bronze exvotos and jewelry.
Top Floor: From the top of the stairs, turn right, then immediately right again to find a re-created grave site, with several neatly aligned urns and artifacts that would have been buried with the deceased. Some of these were funeral dowries (called corredo) that the dead would pack along. You’ll see artifacts such as mirrors, coins, hardware for vases, votive statues, pots, pans, and jewelry. On the landing are fragments from Volterra’s acropolis—a site now occupied by the Medici Fortress.
• After your visit, duck across the street to the alabaster showroom and the wine bar (both described next).
Alab’Arte offers a fun peek into the art of alabaster. Their showroom is across from the Etruscan Museum, but to find their powdery workshop, go a block downhill, in front of Porta Marcoli, where you can watch Roberto Chiti and Giorgio Finazzo at work. They are delighted to share their art with visitors. (Everything—including Roberto and Giorgio—is covered in a fine white dust.) Lighting shows off the translucent quality of the stone and the expertise of these artists. This is not a touristy guided visit, but something far more special: the chance to see busy artisans practicing their craft. For more such artisans in action, visit “Artisan Lane” (Via Porta all’Arco) described earlier, or ask the TI for their list of the town’s many workshops open to the public.
Cost and Hours: Free, showroom—daily 10:30-13:00 & 15:30-19:00, Via Don Minzoni 18; workshop—March-Oct Mon-Sat 9:30-13:00 & 15:00-19:00, closed Sun, usually closed Nov-Feb—call ahead, Via Orti Sant’Agostino 28; tel. 0588-87968, www.alabarte.com.
La Vena di Vino, also just across from the Etruscan Museum, is a fun enoteca where two guys who have devoted themselves to the wonders of wine share it with a fun-loving passion. Each day Bruno and Lucio open six or eight bottles, serve your choice by the glass, pair it with characteristic munchies, and offer fine music (guitars available for patrons) and an unusual decor (the place is strewn with bras). Hang out here with the local characters. This is your chance to try the Super Tuscan wine—a creative mix of international grapes grown in Tuscany. According to Bruno, the Brunello (€7/glass) is just right with wild boar, and the Super Tuscan (€6) is perfect for meditation. Food is served all day, including some microwaved hot dishes or a plate of meats and cheeses. Although Volterra is famously quiet late at night, this place is full of action. Downstairs is a rustic cellar that doubles on weekend nights as a sort of disco.
Cost and Hours: Pay per glass, open Wed-Mon 11:30-1:00 in the morning, closed Tue, 3- to 5-glass wine tastings, shipping options available, Via Don Minzoni 30, tel. 0588-81491, www.lavenadivino.com.
• Volterra’s final sight is perched atop the hill just above the wine bar. Climb up one of the lanes nearby, then walk (to the right) along the formidable wall to find the park.
The Parco Archeologico marks what was the acropolis of Volterra from 1500 B.C. until A.D. 1472, when Florence conquered the pesky city and burned its political and historic center, turning it into a grassy commons and building the adjacent Medici Fortezza. The old fortress—a symbol of Florentine dominance—now keeps people in rather than out. It’s a maximum-security prison housing only about 150 special prisoners. (When you’re driving from San Gimignano to Volterra, you pass another big, modern prison—almost surreal in the midst of all the Tuscan wonder.) Authorities prefer to keep organized crime figures locked up far away from their family ties in Sicily.
The park sprawling next to the fortress (toward the town center) is a rare, grassy meadow at the top of a rustic hill town—a favorite place for locals to relax and picnic on a sunny day. Nearby are the remains of the acropolis (€3.50 to enter, ticket also includes the Roman Theater), but these can be viewed through a fence for free.
Cost and Hours: Park—free to enter, closes at 20:00 in summer, 17:00 in winter.
All the sights listed above are in a tight little zone of the old town, about a 10-minute walk from each other. But if you have time for a stroll, Volterra—perched on a ridge overlooking pristine Tuscan hills—has countryside galore to explore. Get some advice from the TI.
One popular walk is to head to the west end of town, out Porta San Francesco, into a workaday area (dubbed “Borghi,” literally “neighborhoods”) that sees few tourists. Continuing downhill (past the Church of San Giusto), you’ll come to a cliff with a stretch of the original fourth-century B.C. Etruscan wall. Peering over the cliff from here, you can see that Volterra sits upon orange sandy topsoil packed onto clay cliffs, called Le Balze. At various points in its history, the town has been threatened by landslides, and parts of its hilltop have simply disappeared. The big church you see in the distance was abandoned in the late 1800s for fear that it would be swallowed up by the land. The distinctive cliffs surrounding Volterra are called calanchi (similar to the French calanques that slash the Mediterranean coast).
Predictably for a small town, Volterra’s accommodations are limited, and all have their quirks—but there are plenty of places offering a good night’s sleep at a fair price. While it’s convenient to stay inside the old town, the lodgings that are a short walk away are generally a bit cheaper (and much easier for drivers).
$$$ Hotel La Locanda feels stately and old-fashioned. This well-located place (just inside Porta Fiorentina) rents 18 decent rooms with flowery decor and modern comforts (Db-€104, less off-season, 10 percent Rick Steves discount, includes breakfast, air-con, free Wi-Fi, Via Guarnacci 24/28, tel. 0588-81547, www.hotel-lalocanda.com, staff@hotel-lalocanda.com, Giulia, Stefania, and Irina).
$$ Albergo Etruria, on Volterra’s main drag, rents 21 fresh, modern, and spacious rooms within an ancient stone structure. They have a welcoming TV lounge and a peaceful rooftop garden (Sb-€75, Db-€95, Tb-€115, 10 percent discount with cash and this book when you book direct, includes breakfast, fans, free but spotty Wi-Fi, Via Matteotti 32, tel. 0588-87377, www.albergoetruria.it, info@albergoetruria.it, Lisa and Giuseppina are fine hosts).
$$ Albergo Nazionale, with 38 big rooms, is simple, a little musty, short on smiles, popular with school groups, and steps from the bus stop. While the place feels dated, it’s an exceptionally handy location (Sb-€55-70, Db-€70-90, Tb-€90-105, 10 percent discount with cash and this book if you book direct, reception closes at midnight, includes breakfast, free Wi-Fi, Via dei Marchesi 11, tel. 0588-86284, fax 0588-84097, www.hotelnazionale-volterra.it, info@hotelnazionale-volterra.it).
These accommodations are within a 5- to 15-minute walk of the city walls.
$$$ Park Hotel Le Fonti, a dull 10-minute walk downhill from Porta all’Arco, can’t decide whether it’s a business hotel or a resort. The spacious, imposing building feels old and stately, and has 64 rooms, many with views. While generally overpriced (the management knows it’s the only hotel of its kind in Volterra), it can be a good value if you manage to snag a deal. In addition to the swimming pool, guests can use a small spa with sauna, hot tub, and an intriguing “emotional shower” (Db-€89-165, average is about Db-€129 but prices vary wildly depending on season, “superior” room is identical to others but has a view for €20 extra, “deluxe” room with terrace costs €30 extra, includes breakfast, elevator, pay Wi-Fi in lobby, on-site restaurant, wine bar, free parking, Via di Fontecorrenti 5, tel. 0588-85219, www.parkhotellefonti.com, info@hotellefonti.com).
$$ Albergo Villa Nencini, just outside of town, is big, professional, and older-feeling, with 36 cheaply furnished rooms. A few rooms have terraces and many have views. Guests also enjoy the large pool and free parking (Sb-€67, Db-€88, Tb-€115, 10 percent discount with cash and this book, includes breakfast, pay Wi-Fi, Borgo Santo Stefano 55, a 15-minute uphill walk to main square, tel. 0588-86386, www.villanencini.it, info@villanencini.it, Nencini family).
$ La Primavera B&B is a great value just a few minutes’ walk outside Porta Fiorentina (near the Roman Theater). Silvia rents five charming, tidy rooms that share a cutesy-country, heavily perfumed lounge. The house is along a fairly busy road, but set back along a pleasant courtyard (Db-€75, Tb-€100, includes breakfast, free Wi-Fi, free parking, Via Porta Diana 15, tel. 0588-87295, mobile 328-865-0390, www.affittacamere-laprimavera.com, info@affittacamere-laprimavera.com).
$ Seminario Vescovile Sant’Andrea has been training priests for more than 500 years. Today, the remaining eight priests still train students, but when classes are over, their 16 rooms—separated by vast and holy halls in an echoing old mansion—are rented very cheaply. Look for the 15th-century Ascension ceramic by Andrea della Robbia, tucked away in a corner upstairs (S-€17, Sb-€22, D-€32, Db-€40, T-€48, Tb-€60, no breakfast, closed Oct-March, elevator, closes at 24:00, groups welcome, free parking, 10-minute walk from Etruscan Museum, Viale Vittorio Veneto 2, tel. 0588-86028, semvescovile@diocesivolterra.it; Alberto, Angela, and Sergio).
$ Chiosco delle Monache, Volterra’s youth hostel, fills a wing of the restored Convent of San Girolamo with 68 beds in 23 rooms. It’s modern, spacious, and very institutional, with lots of services and a tranquil cloister to wander. However, it’s about a 20-minute hike out of town, in a boring area near deserted hospital buildings (bed in 6-bed dorm-€18, breakfast-€6 extra, lockers; Db-€69, includes breakfast; reception closed 13:00-15:00 and after 22:00, elevator, pay Wi-Fi, free parking, Via dell Teatro 4, look for hospital sign from main Volterra-San Gimignano road, tel. 0588-86613, www.ostellovolterra.it, info@ostellovolterra.it). Nearby and run by the same organization, $ Hotel Foresteria has 35 big, utilitarian, new-feeling rooms with great prices but the same location woes as the hostel; it’s worth considering for budget travelers, families, and drivers (Sb-€58, Db-€82, Tb-€103, Qb-€122, includes breakfast, air-con, elevator, pay Wi-Fi, restaurant, free parking, Borgo San Lazzaro, tel. 0588-80050, www.foresteriavolterra.it, info@foresteriavolterra.it).
$$ Podere Marcampo is a newer agriturismo about 2.5 miles outside Volterra on the road to Pisa. Run by Genuino (owner of the recommended Ristorante Enoteca del Duca), his wife Ivana, and their English-speaking daughter Claudia, this peaceful spot has three well-appointed rooms and three apartments, plus a swimming pool with panoramic views. Genuino produces his award-winning Merlot on site and offers €20 wine-tastings with cheese and homemade salami. Cooking classes at their restaurant in town are also available (Db-€94, apartment-€118-195, more expensive mid-July-Aug, includes breakfast with this book, air-con, free Wi-Fi, free parking, tel. 0588-85393, Claudia’s mobile 328-174-4605, www.agriturismo-marcampo.com, info@agriturismo-marcampo.com).
Menus feature a Volterran take on regional dishes. Zuppa alla Volterrana is a fresh vegetable-and-bread soup, similar to ribollita (except that it isn’t made from leftovers). Torta di ceci, also known as cecina, is a savory-pancake-like dish made with garbanzo beans. Those with more adventurous palates dive into trippa (tripe; comes in a bowl like stew), the traditional breakfast of the alabaster carvers. Fegatelli are meatballs made with liver.
Ristorante Enoteca del Duca, with a locally respected chef named Genuino, serves well-presented and creative Tuscan cuisine. You can dine under a medieval arch with walls lined with wine bottles, in a sedate, high-ceilinged dining room (with an Etruscan statuette at each table), on a nice little patio out back, or in their little enoteca (wine cellar). It’s a good place for truffles, and has a friendly staff and a fine wine list (which includes Genuino’s own merlot, plus several much pricier options—choose carefully). The spacious seating, dressy clientele, and calm atmosphere make this a good choice for a romantic splurge (€42 food-sampler fixed-price meal, €10-15 pastas, €15-22 secondi, Wed-Mon 12:30-15:00 & 19:30-22:00, closed Tue, near City Hall at Via di Castello 2, tel. 0588-81510, www.enoteca-delduca-ristorante.it).
Trattoria da Bado, a 10-minute hike out of town, is every local’s favorite for its tipica cucina Volterrana. Giacomo and family offer a rustic atmosphere and serve food with no pretense—“the way you wish your mamma cooks” (meals from 12:30 and 19:30, closed Wed, Borgo San Lazzero 9, tel. 0577-80402, reserve before you go as it’s often full).
Don Beta is a family-run trattoria on the main drag, popular with travelers for its stylish home cooking. Mirko supervises the lively young team as they whisk out steaming plates of pasta and homemade desserts (€6-10 pastas, €12-18 secondi, daily 12:00-14:30 & 19:00-23:00, reservations smart, Via Matteotti 39, tel. 0588-86730, www.donbeta.it).
La Vecchia Lira, bright and cheery, is a classy self-serve eatery that’s a hit with locals as a quick and cheap lunch spot by day (with €5-10 meals), and a fancier restaurant at night (€9-10 pastas, €11-18 secondi; Fri-Wed 11:30-14:30 & 19:00-22:30, closed Thu, Via Matteotti 19, tel. 0588-86180, Lamberto and Massimo).
La Carabaccia feels like an old-school Italian eatery, with a 1950s turquoise color scheme, a deli up front, and a country-rustic dining room in back. They serve only two pastas and two secondi on any given night, so check the menu by the door to be sure you like the choices. Committed to tradition, on Fridays they serve only fish. They whip up €3-4 take-away sandwiches at the deli up front (€7-9 pastas and secondi, Tue-Sun 12:30-14:30 & 19:30-22:00, closed Mon, Piazza XX Settembre 4/5, tel. 0588-86239).
Ristorante il Sacco Fiorentino is a local favorite for traditional cuisine and seasonal seafood specials (€8-10 pastas, €10-15 secondi, Thu-Tue 12:00-15:00 & 19:00-22:00, closed Wed, Via Giusto Turazza 13, tel. 0588-88537).
La Vena di Vino is an enoteca serving up simple and traditional dishes and the best of Tuscan wine in a fun atmosphere. As their hot dishes are microwaved (there’s no real kitchen), come here more for the wine and ambience than for the food (€8-12 meals, closed Tue, Via Don Minzoni 30, tel. 0588-81491). For more details, read the description on here.
Pizzerias: Ombra della Sera dishes out what local kids consider the best pizza in town. At €6-9 a pop, their pizzas make for a cheap date (Tue-Sun 12:00-15:00 & 19:00-22:00, closed Mon, Via Guarnacci 16, don’t confuse this with their second, pricier location on Via Gramsci; tel. 0588-85274). Pizzeria Tavernetta, next door, is more romantic, with delightful indoor and on-the-street seating. Its romantically frescoed dining room upstairs is the classiest I’ve seen in a pizzeria. Marco, who looks like a younger Billy Joel, serves €5-8 pizzas (Thu-Tue 12:00-16:00 & 18:30-22:00, closed Wed, Via Guarnacci 14, tel. 0588-87630).
Picnic: You can assemble a picnic at the few alimentari around town (try Despar Market at Via Gramsci 12, Mon-Sat 7:30-13:00 & 16:00-20:00, Sun 8:30-13:00) and eat in the breezy Archaeological Park.
Gelato: Of the many ice-cream stands in the center, I’ve found L’Isola di Gusto to be reliably high quality (daily 11:00-late, Via Gramsci 3).
In Volterra, buses come and go from Piazza Martiri della Libertà (buy tickets at the tobacco shop right on the piazza; if it’s closed, purchase on board for small extra charge). Most connections—except to Pisa—are with the C.P.T. bus company (www.cpt.pisa.it) through Colle Val d’Elsa (“koh-leh” for short), a workaday town in the valley (4/day Mon-Sat, 1/day Sun, 50 minutes, €2.75). Once in Colle, you must buy another ticket (from another bus company) at the newsstand near the bus stop, or from the blue automated machine at the bus stop (press “F” to toggle to English, then punch in the number for your destination). I’ve listed total journey fares below. The nearest train station is in Saline di Volterra, a 15-minute bus ride away (7/day, 2/day Sun); however, trains from Saline run only to the coast, not to the major bus destinations listed next.
From Volterra by Bus to: Florence (4/day Mon-Sat, 1/day Sun, 2 hours, change in Colle Val d’Elsa, €8.35), Siena (4/day Mon-Sat, no buses on Sun, 2 hours, change in Colle Val d’Elsa, €6.15), San Gimignano (4/day Mon-Sat, 1/day Sun, 2 hours, change in Colle Val d’Elsa, €6.15), Pisa (9/day, 2 hours, change in Pontedera, €5.50).
Just an hour south of Siena (or two hours south of Florence), you’ll find a trio of inviting hill towns, with an emphasis on good wine and scenic country drives: The biggest and most interesting, Montepulciano, has an engaging medieval cityscape draped in a Renaissance coat, wine cellars that plunge deep down into the cliffs it sits upon, and a classic town square. Pienza is a tidily planned Renaissance town that once gave the world a pope. And mellow Montalcino is (even more than most towns around here) all about its wine: Brunello di Montalcino. All three are within about a half-hour drive of each other, making any one of them a good home base for the entire region. Just to the north are the rippling hills of the Crete Senese. Dressed in vibrant green in spring and parched brown in fall, this area is blessed with quintessential Tuscan scenery and dotted with worthwhile countryside accommodations. While my favorite home base for the region is the most interesting town, Montepulciano, you can’t go wrong staying in the countryside or in Montalcino.
Curving its way along a ridge, Montepulciano (mohn-teh-pull-chee-AH-noh) delights visitors with vino and views. Alternately under Sienese and Florentine rule, the city still retains its medieval contrade (districts), each with a mascot and flag. The neighborhoods compete the last Sunday of August in the Bravio delle Botti, where teams of men push large wine casks uphill from Piazza Marzocco to Piazza Grande, all hoping to win a banner and bragging rights. The entire last week of August is a festival: Each contrada arranges musical entertainment and serves food at outdoor eateries along with generous tastings of the local vino.
The city is a collage of architectural styles, but the elegant San Biagio Church, at the base of the hill, is its best Renaissance building. Most visitors ignore the architecture and focus more on the city’s other creative accomplishment, the tasty Vino Nobile di Montepulciano red wine.
The commercial action in Montepulciano centers in the lower town, mostly along Via di Gracciano nel Corso (nicknamed “Corso”). This stretch begins at the town gate called Porta al Prato (near the TI, bus station, and some parking) and winds slowly up, up, up through town—narrated by my self-guided walk, later. Strolling here, you’ll find eateries, gift shops, and tourist traps. The back streets are worth exploring. The main square, at the top of town (up a steep switchback lane from Corso), is Piazza Grande. Standing proudly above all the touristy sales energy, it has a noble, Florentine feel.
The helpful TI is just outside the Porta al Prato city gate, directly underneath the small tree-lined parking lot. It offers a paltry town map for €0.50, books hotels and rooms for no fee, sells train tickets (€1 fee), has an Internet terminal (€3.50/hour), and can book one of the town’s few taxis (Mon-Sat 9:30-12:30 & 15:00-18:00, Sun 9:30-12:30, daily until 20:00 in July-Aug, Piazza Don Minzoni, tel. 0578-757-341, www.prolocomontepulciano.it, info@prolocomontepulciano.it).
Note that on the main square there is an office that looks like a TI, but this is actually a privately run “Strada del Vino” (Wine Road) agency. They don’t have city info, but they do provide wine-road maps, organize wine tours in the city, and lead minibus winery tours farther afield. They also offer other tours (olive oil, cheese, and slow food), cooking classes, and more, depending on season and demand (Mon-Fri 10:00-13:00 & 15:00-18:00, closed Sat-Sun but likely open both days in summer, Piazza Grande 7, tel. 0578-717-484, www.stradavinonobile.it).
Buses leave passengers at the station on Piazza Nenni, down a steep hill from the Porta al Prato gate. From the station, cross the street and head inside the modern orange-brick structure burrowed into the hillside, where there’s an elevator. Ride to level 1, walk straight ahead down the corridor (following signs for centro storico), and ride another elevator to level 1. You’ll pop out at the Poggiofanti Gardens; walk to the end of this park and hook left to find the gate. From here, it’s a 15-minute walk uphill along the Corso, the bustling main drag, to the main square, Piazza Grande (following my self-guided walk, described later). Alternatively, you can wait for the orange shuttle bus that takes you all the way up to Piazza Grande (2/hour, €1.10, buy tickets at bars or tobacco shops); it’s a good strategy to take the bus up and walk back down. There’s a bus stop just before the TI, beside a gray metal canopy over a hotel-booking booth.
Drivers arriving by car should park outside the walls. The city center is a “ZTL” zone—marked with a red circle—where you’ll be fined if you drive; even if you were allowed, you wouldn’t want to tackle the tiny roads inside the city. In general, white lines indicate free parking and blue lines mean pay parking. (If you’re sleeping in town, your hotelier will give you a permit to park within the walls; be sure to get very specific instructions.) Well-signed pay-and-display parking lots ring the city center, usually €1.30/hr. To get the full Montepulciano experience of walking the full length of the town up the Corso, park just outside the Porta al Prato gate (#1 is handiest, but may be full; #2 #3, and #4 are nearby—#3 has a maximum of 1 hour; #5 is near the bus station—you can ride up to the gate on the elevator described above). For a quick surgical strike, make a beeline to the lots up at the top end of town. Follow signs for centro storico, duomo, and Piazza Grande, and use the Fortezza or San Donato lots (flanking the fortress at the top of town). Drivers, be aware that Montepulciano is a very vertical town, and it’s easy to get turned around. Mercifully, it’s also a small town, so backtracking isn’t too time-consuming. Just avoid the ZTL areas, and don’t park on yellow lines.
Market Day: It’s on Thursday morning (8:00-13:00), near the bus station.
Services: There’s no official baggage storage in town, but the TI might let you leave bags with them if they have space and you ask nicely. Public WCs are located at the TI, to the right of Palazzo Comunale, and at the Sant’Agostino Church.
Laundry: A self-service launderette is at Via del Paolino 2, just around the corner from the recommended Camere Bellavista (€4 wash, €4 dry, daily 8:00-22:00, tel. 0578-717-544).
Taxis: To reach the English-speaking Eurospin taxi hotline, call 330-732-723 (€10 for short trips up or down hill; they also provide rides to other towns). For a private taxi, try 348-702-4124. Montepulciano has only a few taxis, so be sure to book well in advance.
(See “Montepulciano” map, here.)
This two-part walk traces the spine of the town, from its main entrance up to its hilltop seat of power. Part 1 begins at Porta al Prato (where you’ll enter if arriving at the bus station, parking at certain lots, or visiting the TI). Note that this part of the walk is uphill; if you’d rather skip straight to the more level part of town, ride the twice-hourly shuttle bus up, or park at one of the lots near the Fortezza. In that case, you can still do Part 1, backwards, on the way down.
This guided stroll takes you up through Montepulciano’s commercial (and touristic) gamut, which curls ever so gradually from the bottom of town to the top. While the street is lined mostly with gift shops, you’ll pass a few relics of an earlier, less commercial age.
Begin in front of the imposing Porta al Prato, one of the many stout city gates that once fortified this highly strategic town. Facing the gate, find the sign for the Porta di Bacco “passagio secreto” on the left. While Montepulciano did have secret passages tunneled through the rock beneath it for coming and going in case of siege, this particular passage—right next to the city’s front door—was probably no secreto...though it works great for selling salami.
Walk directly below the entrance to the Porta al Prato, and look up to see the slot where the portcullis (heavily fortified gate) could slide down to seal things off. Notice that there are two gates, enabling defenders to trap would-be invaders in a no-man’s land where they could be doused with hot tar (sticky and painful). Besides having a drop-down portcullis, each gate also had a hinged door—effectively putting four barriers between the town and its enemies.
Pass through the gate and head a block uphill to reach the Colona dell’ Marzocco. This column, topped with a lion holding the Medici shield, is a reminder that Montepulciano existed under the auspices of Florence—but only for part of its history. Originally the column was crowned by a she-wolf suckling human twins, the civic symbol of Siena. At a strategic crossroads of mighty regional powers (Florence, Siena, and the papal states), Montepulciano often switched allegiances—and this column became a flagpole where the overlords du jour could tout their influence.
The column is also the starting point for Montepulciano’s masochistic tradition, Bravio delle Botti, held on the last Sunday of August, in which each local contrada (fiercely competitive neighborhood, like Siena’s) selects its two stoutest young men to roll a 180-pound barrel up the hill through town. If the vertical climb through town wears you out, be glad you’re only toting a camera.
A few steps up, on the right (at #91), is one of the many fine noble palaces that front Montepulciano’s main strip. The town is fortunate to be graced with so many bold and noble palazzos—Florentine nobility favored Montepulciano as a breezy and relaxed place for a secondary residence. Grand as this palace is, with its stylized lion heads, it’s small potatoes—the higher you go in Montepulciano, the closer you are to the town center...and the fancier the mansions.
Farther up on the right, at #75 (Palazzo Bucelli), take a moment to examine the Etruscan and Roman fragments embedded in the wall (left here by a 19th-century antiques dealer). You can quickly distinguish which pieces came from the Romans and those belonging to the earlier Etruscans by the differences in their alphabets: The “backwards” Etruscan letters (they read from right to left) look closer to Greek than the more modern Roman letters. Many of the fragments show a circle flanked by a pair of inward-facing semicircular designs. The circle represents the libation cup used for drinking at an Etruscan banquet. Banquets were at the center of Etruscan social life, and burial urns depict lounging nobles presenting a feast for the gods.
At the top of the block on the right, pass by the Baroque-style Church of Sant’Agostino. Huff up a few more steps (imagine pushing a barrel now), then take a breather to look back and see the clock tower in the middle of the street. The bell ringer at the top takes the form of the character Pulcinella, one of the wild and carefree revelers familiar from Italy’s comedy theater (commedia dell’arte).
Keep on going, bearing right (uphill) at the fork. At the alimentari on the right (at #23), notice the classic old sign advertising milk, butter, margarine, and olive and canola oil. Soon after, you’ll pass under another sturdy gateway—indicating that this city grew in concentric circles. Passing through the gate and facing the loggia (with the Florentine Medici seal—a shield with balls), turn left and keep on going.
As you huff and puff, notice (on your right, and later on both sides) the steep, narrow, often covered lanes called vicolo (“little street”). You’re getting a peek at the higgledy-piggledy medieval Montepulciano. Only when the rationality of Renaissance aesthetics took hold was the main street realigned, becoming symmetrical and pretty. Beneath its fancy suit, though, Montepulciano remains a rugged Gothic city.
On the left, watch for the hulking former palace (I told you they’d get bigger) that’s now home to Banca Etruria. “Etruria”—a name you’ll see everywhere around here—is a term for the Etruscan territory of today’s Tuscany.
Just after is a fine spot for a coffee break (on the left, at #27): Caffè Poliziano, the town’s most venerable watering hole (from 1868). Step inside to soak in the genteel atmosphere, with a busy espresso machine, newspapers on long sticks, and a little terrace with spectacular views (open long hours daily; it also has free Wi-Fi). It’s named for a famous Montepulciano-born 15th-century poet who was a protégé of Lorenzo the Magnificent de Medici and tutored his two sons. So important is he to civic pride that townspeople are nicknamed poliziani.
A bit farther up and on the right, notice the precipitous Vicolo dello Sdrucciolo—literally “slippery lane.” Any vicolo on the right can be used as a steep shortcut to the upper part of town, while those on the left generally lead to fine views. Many of these side lanes are spanned by brick arches, allowing the centuries-old buildings to lean on each other for support rather than toppling over—a fitting metaphor for the tight-knit communities that vitalize Italian small towns.
Soon the street levels out. Near the end, on the right (at #64), look for the Mazzetti copper shop, crammed full of both decorative and practical items. Because of copper’s unmatched heat conductivity, it’s a favored material in premium kitchens. The production of hand-hammered copper vessels like these is a dying art; in this shop, you can meet gregarious Cesare, who makes them in his workshop just up the street.
To get there, go up the covered lane just after the copper shop (Vicolo Benci, on the right). You’ll emerge partway up the steep street just below the main square. Cesare’s workshop and museum are across the street and a bit to the left (look for Ramaio; for details on him, see here). Steeply uphill, on the right just before reaching the square, Cesare’s buddy Adamo loves to introduce travelers to Montepulciano’s fine wines at the Contucci Cantina (described on here). Visit Cesare and Adamo now, or head up to the square for Part 2 of this walk before coming back down.
Either way, Montepulciano’s main square is just ahead. You made it!
This pleasant, lively piazza is surrounded by a grab bag of architectural sights. If the medieval Palazzo Comunale, or town hall, reminds you of Palazzo Vecchio in Florence, it’s because Florence dominated Montepulciano in the 15th and 16th centuries. The crenellations along the roof were never intended to hide soldiers—they’re just meant to symbolize power. But the big, square central tower makes it clear that the city is keeping an eye out in all directions.
Take a moment to survey the square, where the town’s four great powers stare each other down. Face the Palazzo Comunale, and keep turning to the right to see: the one-time building of the courts (Palazzo del Capitano); the noble Palazzo Tarugi, a Renaissance-arcaded confection; and the aristocratic Palazzo Contucci, with its 16th-century Renaissance facade. (The Contucci family still lives in their palace, producing and selling their own wine.) Continuing your spin, you see the unfinished Duomo looking glumly on, wishing the city hadn’t run out of money for its facade. (Its interior, described later under “Sights and Experiences in Montepulciano,” looks much better.)
A cistern system fed by rainwater draining from the roofs of surrounding palaces supplied the fine well in the corner. Check out its 19th-century pulleys, the grills to keep animals from contaminating the water supply, and the Medici coat of arms (with lions symbolizing the political power of Florence).
Climbing the town hall’s tower rewards you with a windy but commanding view from the terrace below the clock. Go into the Palazzo Comunale, head up the stairs to your left, and pay on the second floor (€3, daily 10:00-18:00, closed in winter).
The street to the left as you face the tower leads to the Fortezza, or fortress. While you might expect the town to be huddled protectively around its fortress, in Montepulciano’s case, it’s built on a distant ledge at the very edge of town. That’s because this fort wasn’t meant to protect the townspeople—but to safeguard its rulers by keeping an eye on those townspeople.
Detour to the Church of San Francesco and Views: From the main square, it’s a short, mostly level walk to a fine viewpoint. You could head down the wide street to the right as you face the tower. But for a more interesting look at Montepulciano behind its pretty Renaissance facades, go instead up the narrow lane between the two Renaissance palaces in the corner of the square. Within just a few steps, you’ll be surrounded not by tidy columns and triangles, but by a mishmash of brick and stone. Pause at the Mueblè il Riccio B&B (with a fine courtyard—peek inside) and look high up across the street to see how centuries of structures have been stitched together, sometimes gracelessly.
Follow along this lane as it bends left, and eventually you’ll pop out just below the main square, facing the recommended Cantine del Redi wine cellar (described later). Turn right and head down toward the church. At #21 (on the left), look for a red-and-gold shield, over a door, with the name Talosa. This marks the home of one of Montepulciano’s contrade, or neighborhoods; birth and death announcements for the contrada are posted on the board next to the door.
Soon you’ll come to a viewpoint (on the right) that illustrates Montepulciano’s highly strategic position. The ancient town sitting on this high ridge was surrounded by powerful forces—everything you see in this direction was part of the Papal States, ruled from Rome. In the distance is Lake Trasimeno, once a notorious swampland that made it even harder to invade this town.
Continue a few steps farther to the big parking lot in front of the church. Head out to the terrace for a totally different view: the rolling hills that belonged to Siena. And keep in mind that Montepulciano itself belonged to Florence. For the first half of the 16th century, those three formidable powers—Florence, Siena, and Rome (the papacy)—vied to control this small area. Take in the view of Montepulciano’s most impressive church, San Biagio—well worth a visit for drivers or hikers (described later).
From here, you can head back up to the main square, or drop into Cantine del Redi to spelunk its wine cellars.
These are listed in the order you’ll reach them on the self-guided walk, above. For me, Montepulciano’s best “experiences” are personal: dropping in on either Adamo, the winemaker at Contucci Cantina, or Cesare, the coppersmith at Ramaio Cesare. Either one will greet you with a torrent of cheerful Italian; just smile and nod, pick up what you can from gestures, and appreciate this rare opportunity to meet a true local character.
Montepulciano’s most popular attraction isn’t made of stone...it’s the famous wine, Vino Nobile. This robust red can be tasted in any of the cantinas lining Via Ricci and Via di Gracciano nel Corso, but the cantina in the basement of Palazzo Contucci is both historic and fun. Skip the palace’s formal wine-tasting showroom facing the square, and instead head down the lane on the right to the actual cellars, where you’ll meet lively Adamo (ah-DAH-moh), who has been making wine since 1953 and welcomes tourists into his cellar. While at the palace, you may meet Andrea Contucci, whose family has lived here since the 11th century. He loves to share his family’s products with the public. Adamo and Signor Contucci usually have a dozen bottles open.
After sipping a little wine with Adamo, explore the palace basement, with its 13th-century vaults. Originally part of the town’s wall, these chambers have been filled since the 1500s with huge barrels of wine. Dozens of barrels of Croatian, Italian, and French oak (1,000-2,500 liters each) cradle the wine through a two-year in-the-barrel aging process, while the wine picks up the personality of the wood. After about 35 years, an exhausted barrel has nothing left to offer its wine, so it’s retired. Adamo explains that the French oak gives the wine “pure elegance,” the Croatian is more masculine, and the Italian oak is a marriage of the two. Each barrel is labeled with the size in liters, the year the wine was barreled, and the percentage of alcohol (determined by how much sun shone in that year). “Nobile”-grade wine needs a minimum of 13 percent alcohol.
Cost and Hours: Free drop-in tasting, daily 8:30-12:30 & 14:30-18:30, Sat-Sun from 9:30, Piazza Grande 13, tel. 0578-757-006, www.contucci.it.
Cesare (CHEH-zah-ray) the coppersmith is an institution in Montepulciano, carrying on his father’s and grandfather’s trade by hammering into existence an immense selection of copper objects in his cavernous workshop. Though his English is limited, he’s happy to show you photos of his work—including the copper top of the Duomo in Siena and the piece he designed and personally delivered to Pope Benedict. Next door, he has assembled a fine museum with items he and his relatives have made, as well as pieces from his personal collection. Cesare is evangelical about copper, and if he’s not too busy, he’ll create personalized mementoes for visitors—he loves meeting people from around the world who appreciate his handiwork (as his brimming photo album demonstrates). Cesare’s justifiable pride in his vocation evokes the hardworking, highly skilled craft guilds that once dominated small-town Italy’s commercial and civic life.
Cost and Hours: Demonstration and museum are free; Cesare is generally in his workshop Mon-Sat 8:00-12:30 & 14:30-18:30, Piazzetta del Teatro, tel. 0578-758-753, www.rameria.com. Cesare’s shop (negozio) is on the main drag, just downhill at Corso #64—look for Rameria Mazzetti, open long hours daily.
This church’s unfinished facade—rough stonework left waiting for the final marble veneer—is not that unusual. Many Tuscan churches were built just to the point where they had a functional interior, and then, for various practical reasons, the facades were left unfinished. But step inside and you’ll be rewarded with some fine art. A beautiful Andrea della Robbia blue-and-white, glazed-terra-cotta Altar of the Lilies is behind the baptismal font (on the left as you enter). The high altar, with a top like a pine forest, features a luminous, early-Renaissance Assumption triptych by the Sienese artist Taddeo di Bartolo. Showing Mary in her dreamy eternal sleep as she ascends to be crowned by Jesus, it illustrates how Siena clung to the Gothic aesthetic—elaborate gold leaf and lacy pointed arches—to show heavenly grandeur at the expense of realism.
Cost and Hours: Free, daily 9:00-13:00 & 15:00-18:30.
The most impressive wine cellars in Montepulciano sit below the Palazzo Ricci, just a few steps off the main square (toward the Church of San Francesco). Enter through the unassuming door and find your way down a spiral staircase—with rounded steps designed to go easy on fragile noble feet, and lined with rings held in place by finely crafted tiny wrought-iron goat heads. You’ll wind up in the dramatic cellars, with gigantic barrels under even more gigantic vaults—several stories high. As you go deeper and deeper into the cellars, high up, natural stone seems to take over the brick. At the deepest point, the atmospheric cave, surrounding a filled-in well, a warren of corridors holds fine wine aging in bottles. Finally you wind up in the shop, where you’re welcome to taste two or three Redi wines for free—or, if you show them this book, they’ll offer you the free wines along with some light food in their spacious tasting room.
Cost and Hours: Free tasting, €7-20 bottles, affordable shipping, daily 10:30-19:00, next to Palazzo Ricci, tel. 0578-757-166, www.dericci.it.
Eclectic and surprisingly modern, but small and ultimately forgettable, this museum collects bits and pieces of local history with virtually no English explanation. The ground floor and cellar hold ancient artifacts and vases, including some Etruscan items. The next two floors are the pinacoteca (art gallery), of which the highlight is the first-floor room filled with colorful Andrea della Robbia ceramic altarpieces. You’ll find a similar della Robbia altarpiece in situ, in the Duomo, for free.
Cost and Hours: €5, Tue-Sun 10:00-13:00 & 15:00-18:00, closed Mon, Via Ricci 10, tel. 0578-717-300.
At the base of Montepulciano’s hill, down a picturesque driveway lined with cypresses, this church—designed by Antonio da Sangallo and built of locally quarried travertine—is Renaissance perfection. The proportions of the Greek cross floor plan give the building a pleasing rhythmic quality. Bramante, who designed St. Peter’s at the Vatican in 1516, was inspired by this dome. The lone tower was supposed to have a twin, but it was never built. The soaring interior, with a high dome and lantern, creates a fine Renaissance space. Walk around the building to study the freestanding towers, and consider a picnic or snooze on the grass in back. The street called Via di San Biagio, leading from the church up into town, makes for an enjoyable, if challenging, walk.
Cost and Hours: Free, normally open daily 8:30-18:30.
$$$ Mueblè il Riccio (“Hedgehog”) is medieval-elegant, with 10 modern and spotless rooms, an awesome roof terrace, and friendly owners. Five are new “superior” rooms with grand views across the Tuscan valleys (Sb-€80, Db-€100, view Db-€110, superior Db-€150, superior Db with balcony-€160, Tb-€116, superior Tb-€180, superior Qb-€200, breakfast-€8, air-con, guest computer and Wi-Fi, limited free parking—request when you reserve, a block below the main square at Via Talosa 21, tel. 0578-757-713, www.ilriccio.net, info@ilriccio.net, Gió and Ivana speak English). Gió and his son Iacopo give tours of the countryside (€50/hour) in one of their classic Italian cars; for details, see their website. Ivana makes wonderful breakfast tarts.
$$ Albergo Duomo is big, modern, and nondescript, with 13 rooms (with small bathrooms) and a comfortable lounge downstairs (small Db-€75, standard Db-€95, Tb-€115, family deals, elevator, air-con in some rooms for €5 extra, free Wi-Fi, loaner laptops, free parking nearby, Via di San Donato 14, tel. 0578-757-473, www.albergoduomo.it, albergoduomo@libero.it, Elisa and Saverio).
$$ Camere Bellavista has 10 charming, tidy rooms. True to its name, each room has a fine view—though some are better than others. Room 6 has a view terrace worth reserving (Db-€80, terrace Db-€100, cash only, optional €3-10 breakfast at a bar in the piazza, lots of stairs with no elevator, free Wi-Fi, Via Ricci 25, no reception—call before arriving or ring bell, mobile 347-823-2314, www.camerebellavista.it, bellavista@bccmp.com, Gabriella speaks only a smidgen of English).
$$ Vicolo dell’Oste B&B, just off the main drag halfway up through town, has five modern rooms with fully outfitted kitchenettes (Db-€95-100, Tb-€130, Qb-€140, includes breakfast at nearby café, free Wi-Fi, on Via dell’Oste 1—an alley leading right off the main drag just after Caffè Poliziano and opposite the farmacia at #47, tel. 0578-758-393, www.vicolodelloste.it, info@vicolodelloste.it, Luisa and Giuseppe).
Countryside Options near Montepulciano: If you’d rather be in the country than in town, don’t miss the nearby options listed under “Sleeping near Pienza,” later—about a 15-minute drive from Montepulciano.
Ai Quattro Venti is fresh, flavorful, fun, and right on Piazza Grande, with a simple dining room and outdoor tables right on the square. It distinguishes itself by offering reasonable portions of tasty, unfussy Tuscan food in an unpretentious setting. Try their very own organic olive oil and wine (€8-9 pastas, €9-10 secondi, Fri-Wed 12:30-14:30 & 19:30-22:30, closed Thu, next to City Hall on Piazza Grande, tel. 0578-717-231, Chiara).
Osteria dell’Aquacheta is a carnivore’s dream come true, famous among locals for its excellent beef steaks. Its long, narrow room is jammed with shared tables and tight seating, with an open fire in back and a big hunk of red beef lying on the counter like a corpse on a gurney. Giulio, with a pen tucked into his ponytail, whacks off slabs with a cleaver, confirms the weight and price with the diner, and tosses the meat on the grill—seven minutes per side. Steaks are sold by weight (€3/100 grams, or etto, one kilo is about the smallest they serve, two can split it for €30). They also serve hearty €6 pastas and salads and a fine house wine. In the tradition of old trattorias, they serve one glass, which you use alternately for wine and water (Wed-Mon 12:30-15:00 & 19:30-22:30, closed Tue, Via del Teatro 22, tel. 0578-758-443 or 0578-717-086).
Osteria del Conte, an attractive but humble family-run bistro, offers a €30 menù del Conte—a four-course dinner of local specialties including wine—as well as à la carte options and cooking like mom’s. While the interior is very simple, they also have outdoor tables on a stony street at the edge of the historic center (€7-8 pastas, €9-14 secondi, Thu-Tue 12:30-14:30 & 19:30-21:30, closed Wed, Via San Donato 19, tel. 0578-756-062).
Le Pentolaccia is a small, family-run restaurant at the upper, relatively untouristy end of the main drag. With both indoor and outdoor seating, they make tasty traditional Tuscan dishes as well as daily fish specials. Cristiana serves, and husband-and-wife team Jacobo and Alessia stir up a storm in the kitchen (€8-10 pastas, €8-15 secondi, Fri-Wed 12:00-15:00 & 19:30-22:30, closed Thu, Corso 86, tel. 0578-757-582).
If you’d enjoy getting out of town for dinner—but not too far—consider the 15-minute drive to the smaller, picturesque hill town of Monticchiello. Just inside the town’s gate is the highly regarded La Porta restaurant, where Daria pleases diners either indoors or out with well-executed traditional Tuscan dishes (€9 pastas, €12-15 secondi, reservations smart; seatings at 12:30, 14:00, 19:30, and 21:30; closed Thu, Via del Piano 1, tel. 0578-755-163, www.osterialaporta.it). If La Porta is closed or you want a bit more contemporary preparation in a modern atmosphere, continue 50 yards up into town and turn right to find La Cantina, run by daughter Deborah (similar prices, Tue-Thu 12:30-15:00 & 19:30-22:00, closed Wed, Via San Luigi 3, tel. 0578-755-280).
Getting There: It’s a straight shot to Monticchiello, but finding the road is the hard part. At the base of Montepulciano, head toward Pienza. Shortly after passing the road to San Biagio Church (on the right), watch on the left for the Albergo San Biagio. Turn off and take the road that runs up past the left side of this big hotel, and follow it all the way to Monticchiello. This is a rough (gravel at times), middle-of-nowhere drive. As a bonus, right near Monticchiello is a twisty serpentine section lined with stoic cypress trees—one of those classic Tuscan images you’ll see on calendars and postcards. It’s also possible to reach Monticchiello more directly from Pienza (ask locals for directions).
Schedule information and bus tickets are available at the TI. All buses leave from Piazza Pietro Nenni. The bus station seems to double as the town hangout, with a lively bar and locals chatting inside. In fact, there’s no real ticket window—you’ll buy your tickets at the bar. Check www.sienamobilita.it for schedules.
From Montepulciano by Bus to: Florence (2/day, 2 hours, LFI bus, €11.20, www.lfi.it), Siena (8/day, none on Sun, 1.25 hours, €6.60), Pienza (8/day, 30 minutes, €2.50), Montalcino (4/day Mon-Fri, 3/day Sat, none Sun, change in Torrenieri, 1-1.25 hours total, €4.90). There are hourly bus connections to Chiusi, a town on the main Florence-Rome rail line (40 minutes, €3.40); Chiusi is a much better bet than the distant Montepulciano station (5 miles away), which is served only by milk-run trains, but it is handy on Sundays if you want to go to Siena. Buses connect Montepulciano’s bus station and its train station (6/day, none on Sun).
To Montalcino: This connection is problematic by public transportation—consider asking at the TI for a taxi, or call Eurospin taxi company, listed under “Helpful Hints” earlier. Although expensive (about €70), a taxi could make sense for two or more people. Otherwise you can take a bus to Torrenieri, then change to get to Montalcino (2 hours). Drivers find route S-146 to Montalcino particularly scenic (see “The Crete Senese” on here). Cortona is another awkward connection, involving a bus to Chiusi, then a 30-minute train ride to the Camuccia-Cortona train station, four miles below town with poorly timed bus connections to Cortona itself. Consider taking a taxi (about €40).
Set on a crest and surrounded by green, rolling hills, the small town of Pienza packs a lot of Renaissance punch. In the 1400s, locally born Pope Pius II of the Piccolomini family decided to remodel his birthplace in the style that was all the rage: Renaissance. Propelled by papal clout, the town of Corsignano was transformed—in only five years’ time—into a jewel of Renaissance architecture. It was renamed Pienza, after Pope Pius. The plan was to remodel the entire town, but work ended in 1464 when both the pope and his architect, Bernardo Rossellino, died. Their vision—what you see today—was completed a century later. The architectural focal point is the square, Piazza Pio II, surrounded by the Duomo and the pope’s family residence, Palazzo Piccolomini. While Piazza Pio II is Pienza’s pride and joy, the entire town—a mix of old stonework, potted plants, and grand views—is fun to explore, especially with a camera or sketchpad in hand. You can walk every lane in the tiny town in a few minutes.
Cute as the town is, it’s far from undiscovered; tourists can flood Pienza in peak season, and boutiques selling gifty packages of pecorino cheese and local wine greatly outnumber local shops. While it offers fine views of the surrounding countryside, Pienza is situated on a relatively flat plateau rather than the steep pinnacle of more dramatic towns like Montepulciano and Montalcino. For these reasons, it’s made to order as a stretch-your-legs break to enjoy the setting, and perhaps tour the palace, but it’s not ideal for lingering overnight.
Nearly every shop sells the town’s specialty: Pecorino cheese. This pungent sheep’s cheese is available fresh (fresco) or aged (secco), and sometimes contains other ingredients, such as truffles or peppers. Look on menus for warm Pecorino (al forno or alla griglia), often topped with honey or pears and served with bread. Along with a glass of local wine, this just might lead you to a new understanding of la dolce vita.
Tourist Information: The TI is 10 yards up the street from Piazza Pio II, inside the Diocesan Museum (Wed-Mon 10:00-13:00 & 14:30-18:00, closed Tue, Sat-Sun only in Nov-March, Corso il Rossellino 30, tel. 0578-749-905). Ignore the kiosk just outside the gate, labeled Informaturista, which is a private travel agency.
Arrival in Pienza: Buses drop you just a couple of blocks directly in front of the town’s main entrance. If driving, read signs carefully—some parking spots are reserved for locals, others require the use of a cardboard clock, and others are pay-and-display. Parking is tight, so if you don’t see anything quickly, head for the large lot at Piazza del Mercato near Largo Roma outside the old town: As you approach town and reach the “ZTL” cul-de-sac (marked with a red circle) surrounding the park right in front of the town gate, head up the left side of town and look for the turnoff on the left for parking (€1.50/hour, closed Fri morning during market).
Helpful Hints: Market day is Friday morning at Piazza del Mercato, just outside the town walls. A public WC, marked gabinetti pubblici, is on the right as you face the town gate from outside, on Piazza Dante Alighieri (down the lane next to the faux TI).
One of Italy’s classic piazzas, this square is famous for its elegance and artistic unity. The square and the surrounding buildings were all designed by Rossellino to form an “outdoor room.” Spinning around clockwise, you’ll see City Hall (13th-century bell tower with a Renaissance facade and a fine loggia), the Bishop’s Palace (now the Diocesan Museum), the Duomo, and the Piccolomini family palace. Just to the left of the church, a lane leads to the best viewpoint in town (described later).
Its classic, symmetrical Renaissance facade—dated 1462 with the Piccolomini family coat of arms immodestly front and center—dominates Piazza Pio II. The interior is charming, with several Gothic altarpieces and painted arches. Windows feature the crest of Pius II, with five half-moons advertising the number of crusades that his family funded. The interior art is Sienese Gothic, on the cusp of the Renaissance. As the local clay and tufo stone did not make an ideal building foundation, the church is slouching. The church’s cliff-hanging position bathes the interior in light, but also makes it feel as if the building could break in half if you jumped up and down. See the cracks in the apse walls, and get seasick behind the main altar.
Cost and Hours: Free, generally open daily 7:00-13:00 & 14:30-19:00.
The home of Pius II (see here) and the Piccolomini family (until 1962) can only be visited on an escorted audioguide tour (about 30 minutes total). You’ll see six rooms (dining room, armory, bedroom, library, and so on), three galleries (art-strewn hallways), and the panoramic loggia before being allowed to linger in the beautiful hanging gardens. The drab interiors, faded paintings, coffered ceilings, and scuffed furniture have a mothballed elegance that makes historians wish they’d seen it in its heyday. The audioguide very dryly identifies each item in each room but (sadly) does little to muster enthusiasm for this small-town palace that once hosted a big-name player in European politics. While it’s not quite the fascinating slice of 15th-century aristocratic life that it could be (I’d like to know more about the pope’s toilet), this is still the best small-town palace experience I’ve found in Tuscany (it famously starred as the Capulets’ home in Franco Zeffirelli’s 1968 Academy Award-winning Romeo and Juliet). You can peek inside the door for free to check out the well-preserved, painted courtyard. In Renaissance times, most buildings were covered with elaborate paintings like these.
Cost and Hours: €7, Tue-Sun 10:00-13:00 & 14:00-18:30, first tour departs at 10:30, last tour at 18:00, closed Mon, Piazza Pio II 2, tel. 0578-748-392, www.palazzopiccolominipienza.it.
This measly collection of religious paintings, ecclesiastical gear, altarpieces, and old giant hymnals from local churches fills one room of the cardinal’s Renaissance palace. The art is provincial Sienese, displayed in chronological order from the 12th through 17th centuries (but with no English information).
Cost and Hours: €4.50, same hours as TI—which is where you’ll buy the ticket, Corso il Rossellino 30.
As you face the church, the upper lane leading left brings you to the panoramic promenade. Views from the terrace include the Tuscan countryside and, in the distance, Monte Amiata, the largest mountain in southern Tuscany. You can exit the viewpoint down the first alley, Via del’Amore—the original Lover’s Lane—which leads back to the main drag.
While I wouldn’t hang my hat in sleepy Pienza itself, some fine countryside options sit just outside town—including one of my favorite Italian agriturismo experiences, Cretaiole. Location-wise, this is an ideal home base: midway between Montepulciano and Montalcino, and immersed in Tuscan splendor. Three or four of the iconic Tuscan landscape vistas are within 10 or 15 minutes’ drive of Pienza; you’ll make your sightseeing commute along extremely scenic roads with plenty of strategically located pullouts.
$$$ Agriturismo Cretaiole, in pristine farmland just outside Pienza, is a terrific value if you want to call Tuscany home for a long stay. It’s warmly run by reformed city-slicker Isabella, her country-boy husband Carlo, and their family. This family-friendly farm welcomes visitors for weeklong stays (generally Sat-Sat) in six comfortable apartments. Eager to share their local traditions, they offer travelers a rich cultural education. Carlo is a professional olive-oil taster. Carlo’s father, Luciano, is in charge of the grappa and tends the vegetable garden (take your pick of the free veggies). And Isabella is a tireless Jill-of-all-trades, who prides herself on personally assisting each of her guests to find exactly the Tuscan experience they’re dreaming of. While there’s no swimming pool—for philosophical reasons—many thoughtful touches and extras, such as Wi-Fi, mountain bikes, and loaner mobile phones, are provided. Isabella also organizes fairly priced optional activities such as pasta-making and olive-oil tasting classes, family-style Tuscan dinners, winery tours, truffle hunts and grape and olive harvesting (in season), visits to the studios of local artisans, side-trips to Siena, watercolor classes, dinner at a local monastery, and more (Db-€825/week, small Db apartment-€990/week, large Db apartment-€1,290/week, same apartment for four-€1,595/week, these prices promised with this book in 2014, fewer activities and lower prices mid-Nov-mid-March, tel. 0578-748-083, Isabella’s mobile 338-740-9245, www.cretaiole.it, info@cretaiole.it). It’s on the Montalcino-Pienza road (S-146), about 11 miles out of Montalcino, and about 2.5 miles from Pienza. While they prefer weeklong stays, when things are slow they may accept guests for as few as three nights (for this you must book less than a month in advance, Db-€120, 3-night minimum). The same family runs two other properties, with the same activities and personal attention as the main agriturismo: Le Casine di Castello is a townhouse with two units and the same prices as Cretaiole, but guests have more independence. The more upscale Casa Moricciani is a swanky villa featuring dreamy views, plush interiors, loads of extras, and pure Tuscan luxury (€2,900/week upstairs or €3,900/week downstairs, each with 2 bedrooms and 2 bathrooms). Both properties are in the untouristy medieval village of Castelmuzio, five miles north of Pienza; for details, see www.buongiornotoscana.com.
$$$ Fonte Bertusi, nearly across the road from Cretaiole, is well-run by young couple Manuela and Andrea, Andrea’s father Eduardo, and their attention-starved cats. This imaginative family has scattered vivid, whimsical bits and pieces of artwork around the grounds and in the rooms. The eight apartments are simple—mixing rustic decor with avant-garde creations—and a bit pricey, but the setting is sublime (nightly rate: 1-bedroom apartment-€130, 2-bedroom apartment-€260, includes breakfast; weekly rate: €710-1,010, €40 extra per person for breakfast all week; free Wi-Fi, laundry service, swimming pool, communal BBQ and outdoor kitchen, just outside Pienza toward San Quirico d’Orcia on the right—don’t confuse it with the turnoff for “Il Fonte” just before, tel. 0578-748-077, www.fontebertusi.it, info@fontebertusi.it).
Bus tickets are sold at the bar/café (marked Il Caffè, closed Tue) just outside Pienza’s town gate (or pay a little extra and buy tickets from the driver). Buses leave from a few blocks up the street, directly in front of the town entrance. Montepulciano is the nearest transportation hub to other points.
From Pienza by Bus to: Siena (6/day, none on Sun, 1.5 hours, €4.40), Montepulciano (8/day, 30 minutes, €2.50), Montalcino (4/day Mon-Fri, 3/day Sat, none sun, change in Torrenieri, 45-60 minutes total, €3.40).
On a hill overlooking vineyards and valleys, Montalcino—famous for its delicious and pricey Brunello di Montalcino red wines—is a must for wine lovers. It’s a pleasant, low-impact town with a fine ambience but little sightseeing. Everyone touring this area seems to be relaxed and in an easy groove...as if enjoying a little wine buzz.
In the Middle Ages, Montalcino (mohn-tahl-CHEE-noh) was considered Siena’s biggest ally. Originally aligned with Florence, the town switched sides after the Sienese beat up Florence in the Battle of Montaperti in 1260. The Sienese persuaded the Montalcini to join their side by forcing them to sleep one night in the bloody, Florentine-strewn battlefield.
Montalcino prospered under Siena, but like its ally, it waned after the Medici family took control of the region. The village became a humble place. Then, in the late 19th century, the Biondi Santi family created a fine, dark red wine, calling it “the brunette” (Brunello). Today’s affluence is due to the town’s much-sought-after wine.
If you’re not a wine lover, you may find Montalcino a bit too focused on vino, but one sip of Brunello makes even wine skeptics believe that Bacchus was onto something. Note that Rosso di Montalcino (a younger version of Brunello) is also very good, at half the price. Those with a sweet tooth will enjoy crunching the Ossi di Morta (“bones of the dead”) cookies popular in Tuscany.
Sitting atop a hill amidst a sea of vineyards, Montalcino is surrounded by walls and dominated by the Fortezza (a.k.a. “La Rocca”). From here, roads lead down into the two main squares: Piazza Garibaldi and Piazza del Popolo.
Tourist Information: The helpful TI, just off Piazza Garibaldi in City Hall, can find you a room for no fee. They sell bus tickets; can call ahead to book a visit at a countryside winery (€1-per-person service fee); and have information on taxi service to nearby towns, abbeys, and monasteries (daily 10:00-13:00 & 14:00-17:30, tel. 0577-849-331, www.prolocomontalcino.com).
Arrival in Montalcino: The bus station is on Piazza Cavour, about 300 yards from the town center. From here, simply follow Via Mazzini straight into town.
Drivers coming in for a short visit should drive around the old gate under the fortress, take the first right (follow signs to Fortezza; it looks almost forbidden), and grab a spot in the pay lot at the fortress (€1.50/hour, free 20:00-8:00). If you miss this lot—or if it’s full—follow the town’s western wall toward the Madonna del Socorrso church and a long pay lot with the same prices. Otherwise, park for free a short walk away.
Helpful Hints: Market day is Friday (7:00-13:00) on Viale della Libertà (near the Fortezza). Day-trippers be warned: Montalcino has no baggage storage.
This 14th-century fort, built under the rule of Siena, is now little more than an empty shell. People visit for its wine bar (see here). You can climb the ramparts to enjoy a panoramic view of the Asso and Orcia valleys, or enjoy a picnic in the park surrounding the fort.
Cost and Hours: €4 for rampart walk—buy ticket and enter in the wine bar, €6 combo-ticket includes Civic Museum (sold only at museum), daily 9:00-20:00, until 18:00 Nov-March, last entry 30 minutes before closing.
All roads in tiny Montalcino seem to lead to the main square, Piazza del Popolo (“People’s Square”).
Since 1888, the recommended Caffè Fiaschetteria Italiana has been the elegant place to enjoy a drink. Its founder, inspired by Caffè Florian in Venice, brought fine coffee to this humble town of woodcutters.
City Hall was the fortified seat of government. It’s decorated by the coats of arms of judges who, in the interest of fairness, were from outside of town. Like Siena, Montalcino was a republic in the Middle Ages. When Florentines took Siena in 1555, Siena’s ruling class retreated here and held out for four more years. The Medici coat of arms (with the six pills), which supersedes all the others, is a reminder that in 1559 Florence finally took Montalcino.
The one-handed clock was the norm until 200 years ago. For five centuries the arcaded loggia hosted the town market. And, of course, it’s fun to simply observe the passeggiata—these days mostly a parade of tourists here for the wine.
While it’s technically three museums in one (archaeology, medieval art, and modern art), and it’s surprisingly big and modern for this little town, Montalcino’s lone museum ranks only as a decent bad-weather activity. The archaeology collection, filling the cellar, includes interesting artifacts from the area dating back as far as—gulp—200,000 B.C. With good English explanations, this section also displays a mannequin dressed as an Etruscan soldier and a model of the city walls in early Roman times. The ground, first, and second floors hold the medieval and modern art collections, with an emphasis on Gothic sacred art (with works from Montalcino’s heyday, the 13th to 16th centuries). Most of the art was created by local artists. The ground floor is best, with a large collection of crucifixes and the museum’s highlights, a glazed-terra-cotta altarpiece and statue of St. Sebastian, both by Andrea della Robbia.
Cost and Hours: €4.50, €6 combo-ticket includes rampart walk at Fortezza, Tue-Sun 10:00-13:00 & 14:00-17:50, closed Mon, Via Ricasoli 31, to the right of Sant’Agostino Church, tel. 0577-846-014.
$$$ Hotel Dei Capitani, at the end of town near the bus station, has plush public spaces, an inviting pool, and a cliffside terrace offering plenty of reasons for lounging. About half of the 29 rooms come with vast Tuscan views for the same price (request a view room when you reserve), the nonview rooms are bigger, and everyone has access to the terrace (Db-€138 with this book in 2014, extra bed-€40, air-con, elevator, free guest computer and Wi-Fi, limited free parking—first come, first served, Via Lapini 6, tel. 0577-847-227, www.deicapitani.it, info@deicapitani.it).
$$ Palazzina Cesira, right in the heart of the old town, is a gem renting five spacious and tastefully decorated rooms in a fine 13th-century residence with a palatial lounge and a pleasant garden. You’ll enjoy a refined and tranquil ambience, a nice breakfast (with eggs), and the chance to get to know Lucilla and her American husband Roberto, who are generous with local advice (Db-€105, suites-€125, cash only, 2-night minimum, 3-night minimum on holiday weekends, air-con, free guest computer and Wi-Fi, free off-street parking, Via Soccorso Saloni 2, tel. 0577-846-055, www.montalcinoitaly.com, p.cesira@tin.it).
$ Affittacamere Mariuccia has three small, colorful, good-value, Ikea-chic rooms on the main drag over a heaven-scented bakery (Sb-€40, Db-€50, air-con, breakfast-€10 extra, check in across the street at Enoteca Pierangioli before 20:00 or let them know arrival time, Piazza del Popolo 16, rooms at #28, tel. 0577-849-113, mobile 348-392-4780, www.affittacameremariuccia.it, enotecapierangioli@hotmail.com, Alessandro and Stefania speak English).
$ Albergo Giardino, old and basic, has nine big simple rooms, no public spaces, and a convenient location near the bus station (Db-€55-60, 10 percent discount with this book outside May and Sept, no breakfast, Piazza Cavour 4, tel. 0577-848-257, mobile 338-684-3163, albergoilgiardino@virgilio.it; Roberto speaks English; dad Mario doesn’t).
$$ La Crociona, an agriturismo farm and working vineyard, rents seven fully equipped apartments. Fiorella Vannoni and Roberto and Barbara Nannetti offer cooking classes and tastes of the Brunello wine grown and bottled on the premises (Db-€95, or €65 in Oct-mid-May; Qb-€130, or €95 in Oct-mid-May; lower weekly rates, metered gas heating, laundry-€8/load, covered pool, hot tub, fitness room, La Croce 15, tel. 0577-847-133 or 0577-848-007, www.lacrociona.com, info@lacrociona.com). The farm is two miles south of Montalcino on the road to the Sant’Antimo Monastery; don’t turn off at the first entrance to the village of La Croce—wait for the second one, following directions to Tenuta Crocedimezzo e Crociona. A good restaurant is next door.
(See “Montalcino” map, here.)
Re di Macchia is an invitingly intimate restaurant where Antonio serves up the Tuscan fare Roberta cooks. Look for their seasonal menu and Montalcino-only wine list. Try the €25 fixed-price meal, and for €17 more, have it paired with local wines carefully selected to accompany each dish (€9-10 pastas, €16 secondi, Fri-Wed 12:00-14:00 & 19:00-21:00, closed Thu, reservations strongly recommended, Via Soccorso Saloni 21, tel. 0577-846-116).
Taverna il Grappolo Blu is unpretentious, friendly, and serious about its wine, serving local specialties and vegetarian options to an enthusiastic crowd (€8-9 pastas, €9-14 secondi, daily 12:00-15:00 & 19:00-22:00, reservations smart, near the main square, a few steps off Via Mazzini at Scale di Via Moglio 1, tel. 0577-847-150, Luciano, www.grappoloblu.it).
Ristorante-Pizzeria San Giorgio is a homey trattoria/pizzeria with kitschy decor and reasonable prices. It’s a reliable choice for a simple meal (€4-7 pizzas, €8 pastas, €8-12 secondi, daily 12:00-15:00 & 19:00-22:30, Via Soccorso Saloni 10-14, tel. 0577-848-507, Mara).
Picnic: Gather ingredients at the Co-op supermarket on Via Sant’Agostino (Mon-Sat 8:30-13:00 & 16:00-20:00, closed Sun, just off Via Ricasoli in front of Sant’Agostino Church), then enjoy your feast up at the Madonna del Soccorso Church, with vast territorial views.
Wine Bars: Note that two of the places listed under “Wine Bars (Enoteche) in Town,” later, also serve light food.
(See “Montalcino” map, here.)
There are two basic approaches for sampling Montalcino’s wines: at an enoteca in town, or at a countryside winery. Serious wine connoisseurs will enjoy a day of winery-hopping, sipping the wines right where they were created. But if you don’t have the time, or want to try more than one producer’s wines, you might prefer to simply visit a wine bar in town, where you can comfortably taste a variety of vintages before safely stumbling back to your hotel.
(See “Montalcino” map, here.)
Enoteca la Fortezza di Montalcino offers a chance to taste top-end wines by the glass, each with an English explanation. While wine snobs turn up their noses, the medieval setting inside Montalcino’s fort is a hit for most visitors. Spoil yourself with Brunello in the cozy enoteca or at an outdoor table (€13 for 3 tastings, or €22 for 3 “top-end” tastings; €10-18 two-person sampler plates of cheeses, salumi, honeys, and olive oil; daily 9:00-20:00, closes at 18:00 Nov-March, inside the Fortezza, tel. 0577-849-211, www.enotecalafortezza.com, info@enotecalafortezza.com).
Caffè Fiaschetteria Italiana, a classic, venerable café/wine bar, was founded by Ferruccio Biondi Santi, the creator of the famous Brunello wine. The wine library in the back of the café boasts many local choices. A meeting place since 1888, this grand café also serves light lunches and espresso to tourists and locals alike (€6-12 Brunellos by the glass, €3-5 light snacks, €8-12 plates; same prices inside, outside, or in back room; daily 7:30-23:00, closed Thu Nov-Easter, free Wi-Fi, Piazza del Popolo 6, tel. 0577-849-043). And if it’s coffee you need, this place—with its classic 1961 espresso machine—is considered the best in town.
Enoteca di Piazza is one of a chain of wine shops with a system of mechanical dispensers. A “drink card” (like a debit card) keeps track of the samples you take, for which you’ll pay from €1 to €9 for each 50-milliliter taste of the 100 different wines, including some whites—rare in this town. The only nibbles are saltine-type crackers. They hope you’ll buy a bottle of the samples you like, and are happy to educate you in English. (Rule of thumb: A bottle costs about 10 times the cost of the sample. If you buy a bottle, the sample of that wine is free.) While the place feels a little formulaic, it can be fun—the wine is great, and the staff is casual and helpful (daily 9:00-20:00, near Piazza del Popolo at Via Matteotti 43, tel. 0577-848-104, www.enotecadipiazza.com). Confusingly, there are three similarly named places in this same area—this tasting room is a block below the main square.
(See “Montalcino” map, here.)
The surrounding countryside is littered with wineries, some of which offer tastings. A few require an appointment, but many are happy to serve a glass to potential buyers and show them around. The Montalcino TI can give you a list of more than 150 regional wineries and will call ahead for you (€1 fee per person). Or check with the vintners’ consortium (tel. 0577-848-246, www.consorziobrunellodimontalcino.it, info@consorziobrunellodimontalcino.it). These two places listed below are big and capable of handling a steady flow of international visitors; they don’t offer an “authentic” Tuscan or cozy experience, but they are convenient and user-friendly.
Argiano claims to be one of the oldest working wineries in the region, dating back to 1580. About a 10-minute drive south of Montalcino at Sant’Angelo in Colle, their one-hour tour in English includes the vineyards, the exterior of a historic villa, and ancient moldy cellars full of wine casks. They also rent on-site apartments—handy for those who have oversampled (€20 tour includes six wine samples, reserve in advance, tel. 0577-844-037, www.argiano.net, coming by car the last two miles are along a rough-but-drivable track through vineyards).
Banfi, run by the Italian-American Mariani brothers, is huge and touristy. While it’s not an intimate family winery, the grounds are impressive and they’re well set up to introduce the passing hordes to their wines (€15 for 3 tastings, €3.50-25 per glass, daily 10:00-19:00, free tours Mon-Fri at 16:00—reserve in advance, 10-minute drive south of Montalcino in Sant’Angelo Scalo, tel. 0577-877-500, www.castellobanfi.com, reservations@banfi.it).
Bus Tour: If you lack a car (or don’t want to drive), you can take a tour on the Brunello Wine Bus, which laces together a variety of wineries (€25, mid-June-Oct Tue, Thu, and Sat, departs at 9:00, returns at 20:00, tel. 0577-846-021, www.lecameredibacco.com, info@lecameredibacco.com).
Montalcino is poorly connected to just about everywhere except Siena—making it a good day trip if Siena is your base—but other connections are generally workable. Montalcino’s bus station is on Piazza Cavour, within the town walls. Bus tickets are sold at the bar on Piazza Cavour, at the TI, and at some tobacco shops, but not on board (except for the bus to Sant’Antimo). Check schedules at the TI, at the bus station, or at www.sienamobilita.it. The nearest train station is a 20-minute bus ride away, in Buonconvento (bus runs nearly hourly, €2.05).
From Montalcino by Bus: The handiest direct bus is to Siena (6/day Mon-Sat, 4/day Sun, 1.5 hours, €4.90). To reach Pienza or Montepulciano, ride the bus to Torrenieri (5/day Mon-Sat, none on Sun, 20 minutes), where you’ll switch to line #114 for the rest of the way (from Torrenieri: 25 minutes and €3.40 total to Pienza; 45 minutes and €4.90 total to Montepulciano). A local bus runs to Sant’Antimo (3/day Mon-Fri, 2/day Sat, none on Sun, 15 minutes, €1.50, buy tickets on board). Anyone going to Florence by bus changes in Siena; since the bus arrives at Siena’s train station, it’s handier to go the rest of the way to Florence by train. Alternatively, you could take the bus to Buonconvento (described earlier), and catch the train from there to Florence.
Between Siena and the trio of towns described above (Montepulciano, Pienza, Montalcino), the hilly area known as the “Sienese Clay Hills” is full of colorful fields and curvy, scenic roads. The Crete Senese (KRAY-teh seh-NAY-zeh) begins at Siena’s doorstep and tumbles south through some of the most eye-pleasing scenery in Italy. You’ll see an endless parade of classic Tuscan scenes, rolling hills topped with medieval towns, olive groves, rustic stone farmhouses, and a skyline punctuated with cypress trees. You won’t find many wineries here, since the clay soil is better for wheat and sunflowers, but you will find the pristine, panoramic Tuscan countryside featured on countless calendars and postcards.
During the spring, the fields are painted in yellow and green with fava beans and broom, dotted by red poppies on the fringes. Sunflowers decorate the area during June and July, and expanses of windblown grass fill the landscape for much of the early spring and summer.
Most roads to the southeast of Siena will give you a taste of this area, but one of the most scenic stretches is the Lauretana road (Siena-Asciano-San Giovanni d’Asso, S-438, S-451, and SP-60a on road maps; the numbering changes as you drive, but it feels like the same road). To find the Lauretana road from Siena, follow signs for the A-1 expressway; you’ll turn off onto S-438 (look for the sign for Asciano) well before you reach the expressway. You’ll come across plenty of turnouts for panoramic photo opportunities on this road, as well as a few roadside picnic areas and several good accommodations (see “Sleeping in the Crete Senese,” later).
For a break from the winding road, about 15 miles from Siena, you’ll find the quaint and non-touristy village of Asciano. With a medieval town center and several interesting churches and museums, this town offers a rare look at everyday Tuscan living—and it’s a great place for lunch (TI open Tue-Sun 10:30-13:00 & 15:00-18:00, Mon 10:00-13:00, at Corso Matteotti 18, tel. 0577-718-811). If you’re in town on Saturday, gather a picnic at the outdoor market (Via Amendola, 8:00-13:00).
A bit farther along, in Chiusure (about 6 miles south of Asciano, on S-451), follow signs up a steep driveway to the casa di reposo (nursing home) for a fine viewpoint over the Crete Senese, including classic views of jagged calanchi cliffs. From that hilltop, you can also see the Abbey of Monte Oliveto Maggiore. Located 1.5 miles west of Chiursure, the abbey houses a famous fresco cycle of the life of St. Benedict, painted by Renaissance masters Il Sodoma and Luca Signorelli (free, daily 9:15-12:00 & 15:15-18:00, Nov-March until 17:00, Gregorian chanting Sat-Sun at 18:30, Sun also at 11:00, Mon-Fri at 18:15, call to confirm, tel. 0577-707-611, www.monteolivetomaggiore.it).
Once you reach the town of San Giovanni d’Asso—in the heart of the truffle region—it’s a short drive southwest to Montalcino, or southeast to Pienza (each about 12 miles away).
Another scenic drive is the lovely stretch between Montalcino and Montepulciano. This route (S-146 on road maps) alternates between the grassy hills of the Crete Senese and sunbathed vineyards of the Orcia River valley. Stop by Pienza en route.
If pastoral landscapes and easy access to varied towns are your goals, you can’t do much better than sleeping in the Crete Senese. These countryside options sit between Siena, Montepulciano, Pienza, and Montalcino (a 15- to 45-minute drive from any of them). These options line up on (or just off) the scenic roads (S-438 and S-451) south of Siena; I’ve listed them from north to south.
$$$ Recommended local guide Roberto Bechi (see here) has designed and built a new house from scratch that’s immersed in gorgeous Crete Sense scenery (about 15 minutes south of Siena). With five spacious rooms, the house is entirely “green,” with a zero-carbon footprint (Db-€100, mobile 328-425-5648, www.toursbyroberto.com, toursbyroberto@gmail.com). It’s just off road S-438; take the turnoff for Fontanelle.
$ Casanova Agriturismo is for people who really want to stay on an authentic, working farm. This rustic place comes with tractors, plenty of farm smells and noises, and a barn full of priceless Chianina cows. If the five simple rooms and one apartment take a back seat to the farm workings, the lodgings are accordingly inexpensive, and you’ll appreciate the results of their hard work when you dig into one of their fine farm-fresh dinners (€20/person). German Wiebke (who speaks great English and runs the accommodations), her Tuscan husband Bartolo (who works the fields), his mama Paola (who cooks), and the rest of the Conte clan make this a true agriturismo experience (Db-€60, apartment-€80 for 2 and €10 per additional person up to 4, breakfast-€8, free Wi-Fi in some areas, swimming pool, just outside Asciano on road S-451 toward Chiusure, tel. 0577-718-324, mobile 346-792-0859, www.agriturismo-casanova.it, info@agriturismo-casanova.it).
$$ Agriturismo il Molinello (“Little Mill”) rents six apartments, two built over a medieval mill, on the grounds of a working farm with organic produce, olives, and a truffle ground. Hardworking Alessandro and Elisa share their organic produce and offer weekly wine and olive-oil tastings for a minimum of four people; they also lead cooking classes on request. From May through October, they give free guided tours of Siena on Tuesday afternoons. More rustic than romantic, and lacking the dramatic views of some places, this is a nice mix of farm and style. With children, friendly dogs, toys, and a swimming pool, it’s ideal for families (Db-€50-80, Qb-€70-100, apartment for up to 8-€160-200 depending on season and number of people, optional organic breakfast-€9.50, one-week stay required in July-Aug, discounts and no minimum stay off-season, free Wi-Fi in public areas, mountain-bike rentals, biking maps and guided bike tours, between Asciano and the village of Serre di Rapolano—on the road toward Rapolano, 30 minutes southeast of Siena, tel. 0577-704-791, mobile 335-692-5720, www.molinello.com, info@molinello.com).
Cortona blankets a 1,700-foot hill surrounded by dramatic Tuscan and Umbrian views. Frances Mayes’ book Under the Tuscan Sun placed this town in the touristic limelight, just as Peter Mayle’s books popularized the Luberon region in France. But long before Mayes ever published a book, Cortona was popular with Romantics and considered one of the classic Tuscan hill towns. Although it’s unquestionably touristy, unlike San Gimignano, Cortona maintains a rustic and gritty personality—even with its long history of foreigners who, enamored with its Tuscan charm, made this their adopted home.
The city began as one of the largest Etruscan settlements, the remains of which can be seen at the base of the city walls, as well as in the nearby tombs. It grew to its present size in the 13th to 16th centuries, when it was a colorful and crowded city, eventually allied with Florence. The farmland that fills almost every view from the city was marshy and uninhabitable until about 200 years ago, when it was drained and turned into some of Tuscany’s most fertile land.
Art lovers know Cortona as the home of Renaissance painter Luca Signorelli, Baroque master Pietro da Cortona (Berretini), and the 20th-century Futurist artist Gino Severini. The city’s museums and churches reveal many of the works of these native sons.
Most of the main sights, shops, and restaurants cluster around the level streets on the Piazza Garibaldi-Piazza del Duomo axis, but Cortona will have you huffing and puffing up some steep hills. From Piazza Garibaldi, it’s a level five-minute walk down bustling shop-lined Via Nazionale to Piazza della Repubblica, the heart of the town, which is dominated by City Hall (Palazzo del Comune). From this square, a two-minute stroll leads you past the TI, the interesting Etruscan Museum, and the theater to Piazza del Duomo, where you’ll find the recommended Diocesan Museum. These sights are along the more-or-less level spine that runs through the bottom of town; from here, Cortona sprawls upward. Steep streets, many of them stepped, go from Piazza della Repubblica up to the San Niccolò and Santa Margherita churches and the Medici Fortress (a 30-minute climb from Piazza della Repubblica). In this residential area, you’ll see fewer tourists and get a better sense of the “real” Cortona.
In the flat valley below Cortona sprawls the modern, workaday town of Camucia (kah-moo-CHEE-ah), with the train station and other services (such as launderettes) that you won’t find in the hill town itself.
To reach the helpful TI, head to Piazza Signorelli, then walk through the courtyard of the Etruscan Museum and up a short flight of steps, at the back (mid-May-Oct Mon-Sat 9:00-13:00 & 15:00-18:00, Sun 9:00-13:00, Nov-mid-May Mon-Fri 9:00-13:00 & 15:00-18:00, Sat 9:00-13:00, closed Sun, tel. 0575-637-223 or 0575-637-276, www.turismo.provincia.arezzo.it).
Cortona is challenging but doable by public transportation. There are few intercity buses, so your best bet for reaching the town is by train or by car.
By Train: Trains arrive at the unstaffed Camucia station, in the valley four miles below Cortona. Sporadic local buses connect the train station and Piazza Garibaldi in Cortona in about 10 minutes. (If you choose to walk, it’s a long steep climb, and there are no sidewalks.) From the station, walk out the front door and look left to find the bus shelter (with schedules posted). Unfortunately, buses depart only about once per hour—and only twice daily on Sundays—and the schedule is not well-coordinated with train times (purchase €1.60 from driver; you want a bus marked for Cortona rather than the opposite direction, Terontola). On the schedule, departures marked with S do not run during school vacations; those marked with N run only during school vacations. Buses usually drop off at Piazza Garibaldi, but may stop instead at Piazza del Mercato (just outside the city walls near Porta Santa Maria), requiring a 10-minute uphill walk to Piazza Signorelli (for the TI and the Etruscan Museum).
If you’d rather not wait, consider taking a taxi into town (€10, call for Dejan and his seven-seater cab, mobile 348-402-3501—Dejan also arranges day trips, see “Local Guides,” later; or you can ask your hotel to arrange a taxi).
By Car: You’ll find several lots ringing the walls; some are free (white lines), others require payment (blue lines), and still others are for local residents only (yellow lines), so check signs carefully. Your best bet is the large, free lot on Viale Cesare Battisti, just after the big Santo Spirito Church. From here, a series of stairs and escalators take you steeply up to Piazza Garibaldi. Piazza Garibaldi itself may have a handful of pay spots available (marked by blue lines, pay & display, free 20:00-8:00). The small town is actually very long, and it can be smart to drive to the top for sightseeing up there (free parking at Santa Margherita Basilica).
Market Day: The market is on Saturday on Piazza Signorelli (from early morning until 14:00).
Services: The town has no baggage storage, so try asking nicely at a hotel to leave your bag there. The best public WC is located in Piazza del Duomo, under Santa Margherita’s statue.
Tuscan Cooking School: Husband-and-wife team Romano and Agostina hold morning hands-on cooking and cheesemaking classes, as well as wine-, cheese-, and oil-tasting courses, six mornings a week in the converted cellar of a 16th-century monastery, just behind their recommended Ristorante La Bucaccia (closed Mon). In the five-hour class, you’ll prepare two antipasti, two types of pasta, an entrée, and a dessert, which you then get to eat (roughly €90/person, price includes wine, 5 percent discount if you show this book, classes start at 9:30). A three-hour version starts at 11:00 (€70/person; try to book at least a month in advance, evening and personalized classes available). They also offer Italian snack tastings with Romano’s homemade cheeses and cold meats (17:00-23:00, €15—includes a free glass of wine with this book; Via Ghibellina 17, tel. 0575-606-039, www.labucaccia.it, info@labucaccia.it).
Local Guides: Giovanni Adreani exudes energy and a love of his city and Tuscan high culture. He is great at bringing the fine points of the city to life and can take visitors around in his car for no extra charge. As this region is speckled with underappreciated charms, having Giovanni for a day as your driver/guide promises to be a fascinating experience (€110/half-day, €200/day, tel. 0575-630-665, mobile 347-176-2830, www.adreanigiovanni.com, adreanigiovanni@libero.it). Reliable, English-speaking taxi driver Dejan (DAY-zhan) Prvulovic can also take you on full-day tours to Pienza, Montalcino, Siena, Assisi, and Chianti—email him and devise your own itinerary (€250/day depending on number of passengers, mobile 348-402-3501, dejanprvi70@yahoo.it).
(See “Cortona” map, here.)
This introductory walking tour will take you from Piazza Garibaldi and up the main strip to the town center, its piazzas, and the Duomo. (If your bus drops off at Piazza del Mercato, see the map above to locate Piazza Garibaldi.)
• Start at the bus stop in...
Piazza Garibaldi: Many visits start and finish in this square, thanks to its bus stop. While the piazza, bulging out from the town fortifications like a big turret, looks like part of an old rampart, it’s really a souvenir of those early French and English Romantics—the ones who first created the notion of a dreamy, idyllic Tuscany. During the Napoleonic Age, the French built this balcony (and the scenic little park behind the adjacent San Domenico Church) simply to enjoy a commanding view of the Tuscan countryside.
With Umbria about a mile away, Cortona marks the end of Tuscany. This is a major cultural divide, as Cortona was the last town in Charlemagne’s empire and the last under Medici rule. Umbria, just to the south, was papal territory for centuries. These deep-seated cultural disparities were a great challenge for the visionaries who unified the fractured region to create the modern nation of Italy during the 1860s. An obelisk in the center of this square honors one of the heroes of the struggle for Italian unification—the brilliant revolutionary general, Giuseppe Garibaldi.
Enjoy the commanding view from here. Assisi is just over the ridge on the left. Lake Trasimeno peeks from behind the hill, looking quite normal today. But, according to legend, it was blood-red after Hannibal defeated the Romans here in 217 B.C., when 15,000 died in the battle. The only sizable town you can see, on the right, is Montepulciano. Cortona is still defined by its Etruscan walls—remnants of these walls, with stones laid 2,500 years ago, stretch from here in both directions.
Frances Mayes put Cortona on the map for many Americans with her book (and later movie) Under the Tuscan Sun. The book describes her real-life experience buying, fixing up, and living in a run-down villa in Cortona with her husband, Ed. The movie romanticized the story, turning Frances into a single, recently divorced writer who restores the villa and her peace of mind. Mayes’ villa isn’t “under the Tuscan sun” very often; it’s named “Bramasole”—literally, “craving sun.” On the wrong side of the hill, it’s in the shade after 15:00. She and her husband still live there part of each year and are respected members of their adopted community (outside the walls, behind the hill on the left—a 20-minute walk away; ask at the TI for directions if you’d like to see it up close).
• From this square, head into town along...
Via Nazionale: The only level road in town, locals have nicknamed Via Nazionale the ruga piana (flat wrinkle). This is the main commercial street in this town of 2,500, and it’s been that way for a long time. Every shop seems to have a medieval cellar or an Etruscan well. Notice the crumbling sandstone door frames. The entire town is constructed from this grainy, eroding rock.
• Via Nazionale leads to...
Piazza della Repubblica: City Hall faces Cortona’s main square. Note how City Hall is a clever hodgepodge of twin medieval towers, with a bell tower added to connect them, and a grand staircase to lend some gravitas. Notice also the fine wood balconies on the left. In the Middle Ages, wooden extensions like these were common features on the region’s stone buildings. These balconies (not original, but rebuilt in the 19th century) would have fit right into the medieval cityscape. These days, you usually see only the holes that once supported the long-gone wooden beams.
This spot has been the town center since Etruscan times. Four centuries before Christ, an important street led from here up to the hill-capping temple. Later, the square became the Roman forum. Opposite City Hall is the handy, recommended Despar Market Molesini, good for cheap sandwiches. Above that is the loggia—once a fish market, now the recommended Ristorante La Loggetta.
• The second half of the square, to the right of City Hall, is...
Piazza Signorelli: Dominated by Casali Palace, this square was the headquarters of the Florentine captains who used to control the city. Peek into the palace entrance (under the MAEC sign) for a look at the coats of arms. Every six months, Florence would send a new captain to Cortona, who would help establish his rule by inserting his family coat of arms into the palace’s wall. These date from the 15th to the 17th century, and were once painted with bright colors. Cortona’s fine Etruscan Museum (described later, under “Sights in Cortona”) is in the Casali Palace courtyard, which is lined with many more of these family coats of arms. The inviting Caffè del Teatro fills the loggia of the theater that is named for the town’s most famous artist, Luca Signorelli.
• Head down the street just to the right of the museum to...
Piazza del Duomo: Here you’ll find the Diocesan Museum (listed later, under “Sights in Cortona”), cathedral, and (closer to the top of the square) a statue of Santa Margherita. The cathedral’s facade, though recently renovated, still seems a little underwhelming and tucked away. Cortona so loves its hometown saint, Margherita, that it put the energy it would otherwise have invested in its cathedral into the Santa Margherita Basilica, at the top of the hill (at the other end of town—not visible from here). Margherita was a 13th-century rich girl who took good care of the poor and was an early follower of St. Francis and St. Clare. Many locals believe that Margherita protected Cortona from WWII bombs.
The Piazza del Duomo terrace comes with a commanding view of the Tuscan countryside. Notice the town cemetery in the foreground. If you were standing here before the time of Napoleon, you’d be surrounded by tombstones. But Cortona’s graveyards—like other urban graveyards throughout Napoleon’s realm—were cleaned out in the early 1800s to reclaim land and improve hygiene.
• Next, enter the...
Duomo: The Cortona cathedral is not—strictly speaking—a cathedral, because it no longer has a bishop. The white-and-gray Florentine Renaissance-style interior is mucked up with lots of Baroque chapels filling once-spacious side niches. In the rear (on the right) is an altar cluttered with relics. Technically, any Catholic altar, in order to be consecrated, needs a relic embedded in it. Gently lift up the tablecloth (go ahead—the priest here doesn’t mind), and you’ll see a little marble patch that holds a bit of a saint (daily in summer 7:30-13:00 & 15:00-18:30, daily in winter 8:00-12:30 & 15:00-17:30, closed during Mass).
• From here, you can visit the nearby Diocesan Museum, or head back toward Piazza della Repubblica to visit the Etruscan Museum in Piazza Signorelli (both listed next) or to get a bite to eat (see “Eating in Cortona,” later).
Located in the 13th-century Casali Palace and called MAEC for short, this fine gallery (established in 1727) is one of the first dedicated to artifacts from the Etruscan civilization. (In the logo, notice the E is backwards—in homage to the Etruscan alphabet.) This sprawling collection is nicely installed on four big floors with plenty of English information. The bottom two floors (underground) are officially the “Museum of the Etruscan and Roman City of Cortona.” You’ll see an exhibit on the Roman settlement and take a virtual tour of the Etruscan “Il Sodo” tombs (in the nearby countryside). The Cortona Tablet (Tabula Cortonensis, second century B.C.), a 200-word contract inscribed in bronze, contains dozens of Etruscan words archaeologists had never seen before its discovery in 1992. Along with lots of gold and jewelry, you’ll find a seventh-century B.C. grater (for some very aged Parmesan cheese). The top two floors, called the “Accademia,” display an even more eclectic collection, including more Etruscania, Egyptian artifacts, fine Roman mosaics, and a room dedicated to 20th-century abstract works by Severini, all lovingly described in English. A highlight is the magnificent fourth-century B.C. bronze oil lamp chandelier with 16 spouts. On the top floor, peek into the classic old library of the Etruscan Academy, founded in 1727 to promote an understanding of the city through the study of archaeology.
Cost and Hours: €10, €13 combo-ticket includes Diocesan Museum; April-Oct daily 10:00-19:00; Nov-March Tue-Sun 10:00-17:00, closed Mon; Casali Palace on Piazza Signorelli, tel. 0575-637-235, www.cortonamaec.org.
This small collection contains some very choice artworks from the town’s many churches, including works by Fra Angelico and Pietro Lorenzetti, and masterpieces by hometown hero and Renaissance master Luca Signorelli.
Cost and Hours: €5, €13 combo-ticket includes Etruscan Museum, helpful audioguide-€3; April-Oct daily 10:00-19:00; Nov-March Tue-Sun 10:00-17:00, closed Mon; Piazza del Duomo 1, tel. 0575-62-830.
Visiting the Museum: From the entrance, head straight into the Signorelli Room (Sala 4). Signorelli was a generation ahead of Michelangelo and, with his passion for painting ideas, was an inspiration for the younger artist (for more on Signorelli, visit the San Niccolò Church, described later). Take a slow stroll past his very colorful canvases, mostly relocated here from local churches. Among the most striking is Lamentation over the Dead Christ (Compianto sul Cristo Morto, 1502). Everything in Signorelli’s painting has a meaning: The skull of Adam sits under the sacrifice of Jesus; the hammer represents the Passion (the Crucifixion leading to the Resurrection); the lake is blood; and so on. I don’t understand all the medieval symbolism, but it is intense.
Then cut across the top of the stairwell into Sala 3, which was once the nave of the Gesù Church (look up at the beautiful wood-carved ceiling). In Fra Angelico’s sumptuous Annunciation (c. 1430), Mary says “Yes,” consenting to bear God’s son. The angel’s words are top and bottom, while Mary’s answer is upside down (logically, since it’s directed to God, who would be reading while looking down from heaven). Notice how the house sits on a pillow of flowers...the new Eden. The old Eden, featuring the expulsion of Adam and Eve from Paradise, is in the upper left. The bottom edge of the painting comes with comic strip-like narration of scenes from Mary’s life. On the wall to the right, the crucifix (by Pietro Lorenzetti, c. 1325) is striking in its severity. Notice the gripping realism—even the tendons in Jesus’ arms are pulled tight.
Now head back to the stairwell, which is lined with colorful Stations of the Cross scenes by another local but much later artist, the 20th-century’s Gino Severini. These are actually “cartoons,” models used to create permanent pieces for the approach up to the Santa Margherita Basilica. Downstairs, the lower refectory (Sala 6) has a vault with beautiful frescoes (1545) designed by Giorgio Vasari. Back up near the entrance, another staircase leads down to an important but dull collection of vestments and ecclesiastical gear.
Established by St. Francis’ best friend, Brother Elias, this church dates from the 13th century. The wooden beams of the ceiling are original. While the place was redecorated in the Baroque age, some of the original frescoes that once wallpapered the church peek through the whitewash in the second chapel on the left. Francis fans visit for its precious Franciscan relics. To the left of the altar, you’ll find one of Francis’ tunics, his pillow (inside a fancy cover), and his gospel book. Notice how the entire high altar seems designed to frame its precious relic—a piece of the cross Elias brought back from his visit to the patriarch in Constantinople. You’re welcome to climb the altar for a close-up look. In the humble choir area behind the main altar is Elias’ very simple tomb (just a stone slab in the middle of the floor—on a nearby slab, see the Frate Elia da Cortona plaque).
Cost and Hours: Free, daily 9:00-17:30, often open until 19:00 in summer, check with TI; Mass on Sun at 10:00, Mon-Sat at 17:30.
Although this tiny church is rarely open, Signorelli enthusiasts may want to make the pilgrimage—a steep 10-minute walk above the San Francesco Church. While it’s not worth going out of the way for (the picturesque neighborhood surrounding it is, for many, more interesting), it’s an easy detour if you’re hiking up to Santa Margherita. The highlight of this humble church is an altarpiece painted on both sides by Signorelli; it’s usually pulled halfway open so you can see both sides.
Cost and Hours: €1 donation, check with TI before making the trip to make sure it’s open.
From San Niccolò Church, another steep path leads uphill 10 minutes to this basilica, which houses the remains of Margherita, the town’s favorite saint. The red-and-white-striped interior boasts some colorfully painted vaults. Santa Margherita, an unwed mother from Montepulciano, found her calling with the Franciscans in Cortona, tending to the sick and poor. The well-preserved and remarkably emotional 13th-century crucifix on the right is the cross that, according to legend, talked to Margherita.
Cost and Hours: Free, daily 9:00-12:00 & 15:00-19:00 except closed Mon morning, tel. 0575-603-116.
Nearby: Still need more altitude? Head uphill five more minutes to the Medici Fortezza Girifalco (though may be closed—check with TI; if open, likely to be €3, daily late April-Sept 9:00-13:00 & 15:00-18:00, often later in July-Aug, closed Oct-late April, sometimes closed for rehearsals by Italian rock legend Jovanotti, who lives in a villa beyond San Niccolò Church). The views are stunning, stretching all the way to distant Lago Trasimeno.
Guided tours to the tombs (called melone for their melon-like shape), in the locality of Sodo, are complicated to arrange. But the excavation site and bits of the ruins are easy to visit and can be seen even from outside the fence. In the mornings, the guardian often opens the gates for a closer inspection (8:30-13:30). It’s just a couple of miles northwest of Cortona on the Arezzo road (R-71), at the foot of the Cortona hill; ask anyone for “Il Sodo.”
$$$ Hotel San Luca, perched on the side of a cliff, has 54 impersonal business-class rooms, half with stunning views of Lago Trasimeno. While the hotel feels tired and the rooms have seen better days, it’s friendly and conveniently located, right on Piazza Garibaldi at the entrance to the Old Town (Sb-€70, Db-€100, Tb-€130, request a view room when you reserve for no extra charge, popular with Americans and groups, air-con, elevator, free Wi-Fi, Piazza Garibaldi 2, tel. 0575-630-460, www.sanlucacortona.com, info@sanlucacortona.com). If driving, you might find a spot at the small public parking lot at the hotel; otherwise you can park at the big lot down below and ride the escalator up.
$$ Dolce Maria B&B is located in a 16th-century building with high-beamed ceilings. The six rooms are good-value, luminous, and spacious, with tasteful period furnishings and modern bathrooms. The B&B is run by warm and efficient Paola, who also runs the Antico Pozzo restaurant next door—the two businesses share a patio (Db-€80-100, air-con, free Wi-Fi, Via Ghini 12, tel. 0575-601-577, www.cortonastorica.com, info@cortonastorica.com).
$ San Marco Hostel, at the top of town, is housed in a remodeled 13th-century palace (bunk in 4- to 6-bed dorm-€18, in 2-bed room-€25, includes breakfast, lunch or dinner-€11, lockout 10:00-13:00; from Piazza Garibaldi head up steep Via Santa Margherita, then turn left to find Via Maffei 57; tel. 0575-601-765, www.cortonahostel.com, ostellocortona@libero.it).
These accommodations line up along the road that angles downhill from Piazza Garibaldi, within a 10-minute (uphill) walk to the entrance to the Old Town. Drivers may find these handier than the places in town.
$$$ Hotel Villa Marsili is a comfortable splurge just below town. It was originally a 15th-century church, then an elegant 18th-century home. Its 26 rooms and public areas have been recently redecorated and restored, and come with lots of thoughtful little touches. Guests can enjoy an evening aperitif with free snacks on the panoramic terrace. In general, the higher up the room, the fancier the decor and the higher the price. Diane Lane slept in one of the suites while filming Under the Tuscan Sun (Sb-€110, small standard Db-€150, superior Db-€180, deluxe Db-€230, Db suite-€350, extra bed-€25/child or €50/adult, Jacuzzi in deluxe room and suites, air-con, elevator, free guest computer and Wi-Fi, free street parking nearby—first come, first served, otherwise €12, Viale Cesare Battisti 13, tel. 0575-605-252, fax 0575-605-618, www.villamarsili.net, info@villamarsili.net, Marina).
$ Casa Betania, a big, wistful convent with an inviting view terrace, rents 30 fine rooms (mostly twin beds) for the best price in town. While it’s primarily for “thoughtful travelers,” anyone looking for a peaceful place to call home will feel welcome in this pilgrims’ resort. Marco, a big-city lawyer escaping from the rat race, has taken over this place and has turned it into an impressive retreat facility, with conference rooms, a chapel, wine cellar, cooking classes, and more (S-€32, D-€44, Db-€48, Tb-€66, extra bed-€20, breakfast-€4, free Wi-Fi, free parking, about a third of a mile out of town, a few minutes’ walk below Piazza Garibaldi and through iron gates on the right at Via Gino Severini 50, tel. 0575-630-423, www.casaperferiebetania.com, info@casaperferiebetania.com).
$ Villa Santa Margherita, run by the Serve di Maria Riparatrici sisters, rents 22 nicely renovated rooms in a smaller and more traditional-feeling convent just up the street from Casa Betania (Sb-€50, Db-€66, Tb-€86, Qb-€98, elevator, pay Wi-Fi, free parking, Viale Cesare Battisti 17, tel. 0575-178-7203 or 0575-630-336, fax 0575-630-549, www.villasm.it, info@villasm.it).
$ Casa Kita, renting five slightly quirky rooms, is a homey place just below Piazza Garibaldi with fine views from its terrace. You’ll really feel like you’re staying in someone’s home, but the prices are good (Db-€65, free Wi-Fi, 100 yards below Piazza Garibaldi at Vicolo degli Orti 7, tel. 389-557-9893, www.casakita.com, info@casakita.com, Lorenzini family).
Ristorante La Bucaccia is a family-run eatery set in a rustic medieval wine cellar. It’s dressy and romantic. Taking an evangelical pride in their Chianina beef dishes and homemade pastas, Romano hosts and his wife Agostina cooks. Reservations are required for dinner—and worth making (€8-9 pastas, €12-15 secondi, Tue-Sun 12:30-15:30 & 19:00-23:00, closed Mon, show this book for a 5 percent discount and a small free appetizer, Via Ghibellina 17, tel. 0575-606-039, www.labucaccia.it).
Trattoria la Grotta, just off Piazza della Repubblica, is a traditional place serving daily specials to an enthusiastic clientele under grotto-like vaults (€7-9 pastas, €7-20 secondi, good wine by the glass, Wed-Mon 12:00-14:30 & 19:00-22:00, closed Tue, Piazza Baldelli 3, tel. 0575-630-271).
Locanda al Pozzo Antico offers an affordable menu of Tuscan fare, with a focus on fresh, quality produce, and using their own homemade olive oil. Eat in a classy, minimalist dining room or tucked away in a tranquil secret courtyard. Paola is a charming hostess; ask about her cooking classes (€6-9 pastas, €10-16 secondi, Fri-Wed 12:30-14:30 & 19:30-22:00, closed Thu, Via Ghini 12, tel. 0575-62091 or 0575-601-577; Paola, husband Franco, and son Gianni).
Ristorante La Loggetta serves up big portions of well-presented Tuscan cuisine on the loggia overlooking Piazza della Repubblica. While they have fine indoor seating under stone vaults, I’d eat here for the chance to gaze at the square over a meal (€8-10 pastas, €8-15 secondi, Thu-Tue 12:30-15:00 & 19:30-23:00, closed Wed, Piazza Pescheria 3, tel. 0575-630-575).
Fufluns Tavern Pizzeria (that’s the Etruscan name for Dionysus) is easy-going, friendly, and remarkably unpretentious for its location in the town center. It’s popular with locals for its good, inexpensive Tuscan cooking, friendly staff, and stone-and-beam-cozy interior (€5-7 pizza and €6-10 pastas plus big salads, good house wine, Wed-Mon 12:15-14:30 & 19:15-22:30, closed Tue, a block below Piazza della Repubblica at Via Ghibellina 3, tel. 0575-604-140).
Osteria del Teatro tries very hard to create a romantic Old World atmosphere, and does it well. Chef and owner Emiliano serves nicely presented and tasty Italian and local cuisine (taking creative liberties with traditions). There’s good outdoor seating, too. It feels upscale and a bit self-important (€8-9 pastas, €11-16 secondi, Thu-Tue 12:30-14:30 & 19:30-22:00, closed Wed, 2 blocks uphill from the main square at Via Maffei 2—look for the gnomes on the steps, tel. 0575-630-556, www.osteria-del-teatro.it). They also own the bright little restaurant just opposite, Fiaschetteria Fett’unta, which has traditional light snacks and sandwiches.
Enoteca la Saletta, dark and classy with a nice mellow vibe, is good for fine wine and a light meal. You can sit inside surrounded by wine bottles or outside to people-watch on the town’s main drag (€3-5 sandwiches and pizzas, €7-12 pastas and secondi, daily 7:30-24:00, meals served 12:00-24:00, closed Wed in winter, free Wi-Fi, Via Nazionale 26, tel. 0575-603-366).
Picnic: On the main square, the chic little Despar Market Molesini makes tasty sandwiches, served with a smile (see list on counter and order by number, or invent your own), and sells whatever else you might want for a picnic (Mon-Sat 7:00-13:30 & 16:00-20:00, Sun 9:30-13:30, Piazza della Repubblica 23). Munch your picnic across the square on the steps of City Hall, or just past Piazza Garibaldi in the public gardens behind San Domenico Church.
Cortona has good train connections with the rest of Italy through its Camucia-Cortona station. The station is usually unstaffed, but it has two ticket machines: One is in front as you enter the station, and one is outside on platform 1. They take credit cards and cash (change is given). When purchasing, choose the British flag for English, and then follow the clear instructions, delivered with a charming Italian accent. After buying your ticket, immediately validate it in one of the green boxes next to the ticket machine in the main station or on platforms 1 and 3.
To get to the train station at the foot of the hill, take a €10 taxi or hop the €1.20 bus (see “Arrival in Cortona,” earlier; runs only about once hourly; buy tickets at a newsstand or tobacco shop, or buy from driver for €0.40 more). Be sure to confirm with the TI whether these buses leave from Piazza Garibaldi or Piazza del Mercato, outside Porta Santa Maria. Some buses take you only as far as the newsstand that’s 200 yards in front of the station.
From Camucia-Cortona by Train to: Rome (9/day, 2.5 hours, 4 direct, others with change, €11.35), Florence (hourly, 1.5 hours, €9.80), Assisi (every 2 hours, 70 minutes, €5.55), Montepulciano (9/day, 1.5-2 hours, change in Chiusi; because few buses serve Montepulciano’s town center from its distant train station, it’s better to go by train to Chiusi, then by hourly 40-minute bus to Montepulciano, or easier still to take a taxi for about €40), Chiusi (9/day, 40 minutes).
Most trains stop at the Camucia-Cortona train station, but each day, two or three high-speed trains to/from Rome, Florence, and Assisi stop at Terontola, 10 miles away (buses go about hourly to Terontola, leaves from Piazza Garibaldi, 25-30 minutes, €2, check the schedule at the bus stop or pick up printed bus schedule from the TI).
The compelling sight of endless rows of white marble crosses and Stars of David recalls the heroism of the young Americans who fought so valiantly in World War II to free Italy (and ultimately Europe) from the grip of fascism. This particular cemetery is the final resting place of more than 4,000 Americans who died in the liberation of Italy. Climb the hill past the perfectly manicured lawn lined with grave markers, to the memorial, where maps and a history of the Italian campaign detail the Allied advance.
Cost and Hours: Free, daily 9:00-17:00; 7.5 miles south of Florence, off Via Cassia, which parallels the superstrada between Florence and Siena, 2 miles south of Florence Certosa exit on A-1 autostrada; buses from Florence stop just outside the cemetery; tel. 055-202-0020, www.abmc.gov.
Of southern Tuscany’s several evocative monasteries, San Galgano is the best. Set in a forested area called the Montagnolo (“Medium-Size Mountains”), the isolated abbey and chapel are postcard-perfect, though you’ll need a car to get here. Other, more accessible Tuscan monasteries worth visiting include Sant’Antimo (6 miles south of Montalcino) and Monte Oliveto Maggiore (15 miles south of Siena, mentioned in “The Crete Senese,” earlier).
Cost and Hours: €2, June-Aug daily 9:00-20:00, shoulder season until 19:00, Nov-Feb daily 9:30-17:30, tel. 0577-756-738, www.prolocochiusdino.it; concerts sometimes held here in summer—info tel. 055-597-8309, www.festivalopera.it. For a quick snack, a small, touristy bar at the end of the driveway is your only option.
Getting There: Although a bus reportedly comes here from Siena, this sight is realistically accessible only for drivers. It’s just outside Monticiano (not Montalcino), about an hour southwest of Siena. A warning to the queasy: These roads are curvy.
Visiting the Monastery: St. Galgano was a 12th-century saint who renounced his past as a knight to become a hermit. Lacking a cross to display, he created his own by miraculously burying his sword up to its hilt in a stone, à la King Arthur, but in reverse. After his death, a large Cistercian monastery complex grew. Today, all you’ll see is the roofless, ruined abbey and, on a nearby hill, the Chapel of San Galgano with its fascinating dome and sword in the stone.
This picturesque Cistercian abbey was once a powerful institution in Tuscany. Known for their skill as builders, the Cistercians oversaw the construction of Siena’s cathedral. But after losing most of its population in the plague of 1348, the abbey never really recovered and was eventually deconsecrated.
The Cistercian order was centered in France, and the architecture of the abbey shows a heavy French influence. Notice the large, high windows and the pointy, delicate arches. This is pure French Gothic, a style that never fully caught on in Italy (compare it with the chunky, elaborately decorated cathedral in Siena, built about the same time).
As you enter the church, look to the left to see a small section of the cloister wall. This used to surround the garden and was the only place where the monks were allowed to talk, for one hour each day. From inside the church, the empty windows frame the view of the chapel up on the hill.
The upper floor of the actual monks’ quarters (to the side of the abbey) may now be open to the public.
A path from the abbey leads up the hill to the Chapel of San Galgano. The unique, beehive-like interior houses St. Galgano’s sword and stone, recently confirmed to date back to the 12th century. Don’t try and pull the sword from the stone—the small chapel to the left displays the severed arms of the last guy who tried. The chapel also contains some deteriorated frescoes and more interesting sinopie (fresco sketches). The adjacent gift shop sells a little bit of everything, from wine to postcards to herbs, some of it monk-made.
This small hill town (rated ▲▲ for Etruscan fans) was once one of the most important Etruscan cities. Today, it’s a key train junction and a pleasant, workaday Italian village with an enjoyable historic center and few tourists. The hill upon which Chiusi sits is honeycombed with Etruscan tunnels, which you can see in a variety of ways.
Tourist Information: The well-organized TI faces the main square (April-Aug daily 9:00-13:00 & 15:00-17:00, Sept daily 9:00-13:00 & 15:00-17:00, Oct-March Tue-Sun 9:30-12:30, closed Mon, Via Porsenna 79, tel. 0578-227-667, www.prolocochiusi.it).
Arrival in Chiusi: The region’s trains (to Florence, Siena, and Rome—each of these is about an hour away) go through or change at this hub, making Chiusi an easy day trip. There’s no luggage storage at the station, but the TI may be willing to take your bags for a short time. Buses link the train station with the town center two miles away (every 40 minutes, buy tickets at tobacco shop, bus doesn’t run during a gap in the afternoon, taxi costs €10). All buses from the station drop off at a stop just below the center of town (follow well-marked pedestrian signs up to the TI and museums); about half continue on to a stop near the town theater, right downtown. Drivers follow signs for centro storico, then the TI. Easy and free parking lots are a five-minute walk from the center; pay spaces (marked with blue lines) are right downtown, next to the TI and museums. Hertz has a rental-car office near the train station (Via M. Buonarroti 21, tel. 057-822-3000).
Sights in Chiusi: All the town’s sights are within a five-minute walk of each other and the TI.
The Archaeological Museum (Museo Archeologico Nazionale, a.k.a. the Etruscan Museum) thoughtfully presents a high-quality collection with plenty of explanations in English. The collection of funerary urns, some in painted terra-cotta and some in pietra fetida (“stinky stone”), are remarkably intact. You’ll also see exhibits on two tombs in the nearby countryside: a model of the Tomba della Pellegrina, and small-scale reproductions of the frescoes from the Tomba della Scimmia—both mentioned below (€6, daily 9:00-20:00, in the stately Neoclassical-looking building just off the main square at Via Porsenna 93, tel. 0578-20177, www.archeotoscana.beniculturali.it).
The museum also arranges tours to visit the actual Pellegrina and Scimmia tombs; to take part, you’ll need to have your own car and to join a guide (meet at the museum 15 minutes before the tour time). For the Tomba della Pellegrina (Tomb of the Pilgrim), from the Hellenistic period (4th century B.C.), tours depart daily at 11:00 and 16:00 (or 14:30 in winter). This is included in museum admission, and no reservations are necessary—just ask when you arrive. The other, the Tomba della Scimmia (Tomb of the Monkey), is a century earlier and has some well-preserved frescoes (€2; Tue, Thu, and Sat only; March-Oct at 11:00 and 16:00, Nov-Feb at 11:00 and 14:30; this tomb requires an advance reservation).
Troglodyte alert! The Cathedral Museum on the main square has a dark, underground labyrinth of Etruscan tunnels. The mandatory guided tour of the tunnels ends in a large Roman cistern, from which you can climb the church bell tower for an expansive view of the countryside (museum-€2, labyrinth-€3, combo-ticket-€4, daily June-mid-Oct 9:45-12:45 & 16:00-18:30, mid-Oct-May 9:45-12:45 only, 30-minute tunnel tours run every 40 minutes during museum hours, Piazza Duomo 1, tel. 0578-226-490).
Craving more underground fun? The Museo Civico provides hourly tours of the Etruscan water system, which includes an underground lake (€4; May-Oct Tue-Sun at 10:15, 11:30, 12:45, 15:15, 16:30, and 17:45; closed Mon, fewer tours and closed Mon-Wed off-season, call to confirm times, Via II Ciminia 1, tel. 0578-20530, mobile 334-626-6851).
