Montepulciano • Pienza • Montalcino • Heart of Tuscany Drive
Sights and Experiences in Montepulciano
If your Tuscan dreams feature vibrant neon-green fields rolling to infinity, punctuated by snaking, cypress-lined driveways; humble but beautiful (and steep) hill towns; and world-class wines to make a connoisseur weep, set your sights on the heart of this region.
An hour south of Siena, this slice of splendor—which specializes in views and wine—is a highlight, particularly for drivers. With an astonishing diversity of towns, villages, abbeys, wineries, countryside restaurants, and accommodations—all set within jaw-dropping scenery—this subregion of Tuscany is a fine place to abandon your itinerary and just slow down.
Even though the area’s towns sometimes seem little more than a rack upon which to hang the vine-draped hills, each one has its own endearing personality. The biggest and most interesting, Montepulciano, boasts a medieval cityscape wearing a Renaissance coat, wine cellars that plunge deep into the cliffs it sits upon, and a classic town square. Pienza is a sure-of-itself, planned Renaissance town that gave the world a pope. And mellow Montalcino is (even more than most towns around here) all about its wine: the famous Brunello di Montalcino.
As this compact region is hemmed in by Italy’s two main north-south thoroughfares—the A-1 expressway and SR-2 highway—even those with a few hours to spare can get an enticing taste. But ideally, spend two nights and three full days. Many travelers enjoy home-basing here, appreciating not only the area’s many attractions, but also its strategic position for day trips to Siena (less than an hour away), or Volterra, San Gimignano, Florence, and Orvieto (each about 1.5 hours away).
Montepulciano is the most all-around engaging town; it’s the best choice for those without a car (though connections can still be tricky). With easy access to the vineyards, Montalcino makes sense for wine pilgrims. For drivers who’d like to home-base in the countryside, I’ve listed several agriturismi and other rural accommodations.
Here’s a smart plan, assuming you’re coming from Siena. (If coming from the south, do it in reverse.)
Day One: On your way south from Siena, make a winery stop north of Montalcino before settling into Montepulciano (or your countryside accommodation).
Day Two: Follow my Heart of Tuscany Drive, including a sightseeing-and-gelato stop in Pienza. Have dinner back in Montepulciano, or in the nearby countryside.
Day Three: Your day is free to enjoy and sightsee Montepulciano, or drive to countryside attractions (confirm tour availability at La Foce Gardens in advance). You could head to your next destination this afternoon, or spend a third night.
By Car: This area is ideal by car. Distances are short, and it’s easy to mix-and-match sights.
Navigate by town names and use a good map or—better yet—a mapping app to keep you on track. Some sights and wineries are on tiny back lanes, marked only with easy-to-miss, low-profile signs. In small hill towns, make it a habit to park at the lot just outside town and walk in. White lines indicate free parking; blue lines indicate paid parking (pay at the station, then display the ticket on your windshield); and yellow lines are only for locals.
By Public Transportation: While you can reach many of this chapter’s sights by public buses, connections are slow, infrequent, and often require a transfer. Taxis can help connect the dots more efficiently. Montepulciano is the best home base for those without a car (though it’s still not entirely convenient).
A good local guide can help you take full advantage of everything this area has to offer. One with a car can save you lots of time and stress.
Antonella Piredda is smart, well organized, and enjoyably opinionated (€60/hour, 3-hour minimum, €350/all day, she can join you in your car or hire a driver for extra, mobile 347-456-5150, www.antonellapiredda.com, antonella.piredda@live.it).
Roberto Bechi runs all-day minibus tours with a passion for local culture, hands-on experiences, and offbeat sights. The price is reasonable, since he assembles groups of up to eight people to share the experience...and the cost (see website for tour options, RS%—10 percent discount, full-day minibus tours—€100/person, mobile 320-147-6590, www.toursbyroberto.com, toursbyroberto@gmail.com). For more on Roberto’s tours, see here.
A beautiful way to more fully experience this area is to sleep in a farmhouse B&B. For locations, see the “Heart of Tuscany” map. Many of these are working farms (a prerequisite to be officially called an agriturismo) and give a great sense of rural family life. Others are just lovely homes in the countryside. The common denominator is the wonderful people you’ll meet as your hosts.
The Isabella Experience: A variety of accommodations and culturally rich experiences in the countryside near Pienza are warmly run by Isabella, her farmer husband Carlo, and their team. Compare options on the website (www.theisabellaexperience.com) or call Isabella (mobile 338-740-9245)—she’s happy to answer questions. Here’s a rundown:
$$$ Agriturismo Cretaiole is perfect for fully experiencing Tuscany with a group of other travelers. A one-week stay is required (Sat to Sat), which facilitates guests becoming a community of about 20 people—guided by Carlotta—who take part in farm tours, olive oil tastings, pasta-making classes, and more (no air-con or swimming pool, shorter stays may be possible off-season, Carlotta’s mobile 338-835-1614).
$$$$ La Moscadella, on the outskirts of Castelmuzio (five miles north of Pienza), provides a more elevated country-hotel experience—with 12 impeccably decorated rooms and a two-bedroom cottage, plus a gourmet-quality restaurant. Run by Isabella and Doriana, La Moscadella also offers à la carte cultural experiences (weeklong stays preferred but may be flexible, air-con, swimming pool; tel. 0577-665-516, Doriana mobile 338-256-6043).
In the village of Castelmuzio, they rent two other properties: $$$ Le Casine di Castello, a townhouse with two units; and $$$$ Casa Moricciani, a swanky villa with dreamy views and a garden terrace.
More Accommodations Near Pienza: $$$$ Relais Ortaglia, run by Americans Sandy and Phil, rents five pricey rooms in a converted 17th-century farmhouse with modern amenities such as an infinity pool, activities (cooking classes), and a free bottle of prosecco for my readers. Leaving Montepulciano on the main road toward Pienza, watch for the easy-to-miss brown Ortaglia sign on the left, just a half-mile past the San Biagio church turnoff (includes breakfast, 2-night minimum, air-con, mobile 391-163-9887, www.relaisortaglia.com, tuscany@ortaglia.it).
$$$ Fonte Bertusi, a classy and artistic guesthouse between Pienza and Cretaiole, is nicely run by young couple Manuela and Andrea, Andrea’s artist-father Edoardo, and their attention-starved cats. The eight apartments mix rustic decor with avant-garde creations. The setting is sublime, with a grand sunset-view terrace, a communal barbecue and outdoor kitchen, and a swimming pool (laundry service, just outside Pienza toward San Quirico d’Orcia on the right—just after the turnoff for “Il Fonte,” tel. 0578-748-077, Manuela’s mobile 339-655-5648, www.fontebertusi.it, info@fontebertusi.it).
$$ La Bruciata is a family-friendly agriturismo charmingly tucked in the countryside a five-minute drive outside Montepulciano (on the way to Pienza). Can-do Laura and several generations of her family produce wine and olive oil and rent several tasteful, modern rooms that share a peaceful yard with a swimming pool. From April through October, they prefer one-week stays (pay air-con, farm-fresh meals, cooking classes, Via del Termine 9, tel. 0578-757-704, mobile 339-781-5106, www.agriturismolabruciata.it, info@agriturismolabruciata.it). Leaving Montepulciano toward Pienza, turn off on the left for Poggiano, then carefully track brown La Bruciata signs (on gravel roads).
$$ La Crociona, an agriturismo farm and working vineyard, rents seven fully equipped apartments with dated furnishings. Fiorella Vannoni and Roberto and Barbara Nannetti offer cooking classes and tastes of the Brunello wine grown and bottled on the premises (reception open 9:00-13:00 & 14:30-19:30, laundry service, covered pool, hot tub, fitness room, La Croce 15, tel. 0577-847-133, www.lacrociona.com, info@lacrociona.com). The farm is about two miles south of Montalcino on the road to the Sant’Antimo Abbey; don’t turn off at the first entrance to the village of La Croce—wait for the second one, following signs to Tenuta Crocedimezzo e Crociona. A good restaurant is next door.
$$$ B&B Palazzolo La Foce lets you sleep aristocratically in a small villa just below La Foce Gardens. Its seven colorful rooms share a welcoming lounge and breakfast area with a giant fireplace, and an outdoor swimming pool with glorious Tuscan views. All the rooms bask in fine panoramas (no air-con but breezy, Strada della Vittoria 61—check in at gardens’ main entrance to get specific directions to your room, villas also available, tel. 0578-69101, www.lafoce.com, info@lafoce.com, Origo family).
Curving its way along a ridge, Montepulciano (mohn-teh-puhl-CHAH-noh) delights visitors with vino, views, and—perhaps more than any other large town in this area—a sense of being a real, bustling community rather than just a tourist depot.
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, just outside the city walls 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.
Montepulciano is a great starting and ending point for my scenic loop drive through the Heart of Tuscany, described later in this chapter.
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. 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 the Corso), is Piazza Grande. Standing proudly above all the touristy sales energy, the square has a noble, Florentine feel.
The helpful TI is just outside the Porta al Prato city gate, in the small P1 parking lot (Mon-Sat 9:00-13:00 & 15:00-19:00, Sun 9:00-13:00, daily until 20:00 in July-Aug, sells bus and train tickets, Piazza Don Minzoni, tel. 0578-757-341, www.prolocomontepulciano.it).
The office on the main square that looks like a TI is actually the privately run Valdichiana Living agency. They provide wine-road maps, wine tours in the city, minibus winery tours farther afield, and cooking classes and other culinary experiences (Mon-Fri 10:00-13:30 & 14:30-18:00, shorter Sat hours, Sun 10:00-13:00, Piazza Grande 7, tel. 0578-717-484, www.valdichianaliving.it).
Whether you arrive by car or bus, ease your climb to the top of town by riding up on the shuttle bus. For details, see “Helpful Hints,” later.
By Car: Well-signed pay-and-display parking lots ring the city center (marked with blue lines). Some free spaces are mixed in (marked with white lines)—look around before you park, and keep an eye out for time limits.
To start your visit by following my self-guided walk (up the length of the Corso to the main square), park at the north end of town, near the Porta al Prato gate. Around here, the handiest lots are P1 (in front of the TI, with some free spaces) and the unnumbered lot just above, directly in front of the stone gate. If these are full, try lots P2 or P4, or lot P5 near the bus station.
For quicker access to the main square up top, use one of the parking lots at the top end of town: Approaching Montepulciano, follow signs for centro storico, duomo, and Piazza Grande, and use the Fortezza or San Donato lots (flanking the fortress).
Avoid the “ZTL” no-traffic zone (signs marked with a red circle). If you’re sleeping in town, your hotelier can give you a permit to park within the walls; be sure to get very specific instructions before you arrive.
By Bus: Buses leave passengers at the bus station on Piazza Nenni, downhill 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 down the corridor (following signs for centro storico), and ride a second elevator (to a different level 1 and the Poggiofanti Gardens); walk to the end of this park and hook left to find the Porta al Prato gate.
Market Day: It’s on Thursday morning (8:00-13:00), near the bus station.
Services: There’s no official baggage storage, but the TI might let you leave bags with them if they have space. Public WCs are located at the TI, to the left of Palazzo Comunale, and at the Sant’Agostino Church.
Shuttle Bus to the Top of Town: To avoid the hike up through town to Piazza Grande, hop on the orange shuttle bus. It departs about every 15 minutes from the parking lot near the bus station and from the lane leading to the Porta al Prato gate, just above the TI (€1.20, buy tickets at bars, tobacco shops, or the TI).
Laundry: An elegant self-service launderette is at the top of town at Via del Paolino 2, just around the corner from the recommended Camere Bellavista (daily 8:00-22:00, tel. 0578-717-544).
Taxis: Two taxi drivers operate in Montepulciano. Call 330-732-723 for short trips within town (€10 for rides up or down hill); to reach other towns, call 348-733-5343.
This two-part self-guided walk traces the spine of the town from its main entrance up to its hilltop seat of power. Part 1 begins at the big gate at the bottom of town, Porta al Prato (near the TI and several parking lots); Part 2 focuses on the square at the very top of town and the nearby streets. Part 1 is steeply uphill; to skip straight to the more level part of town (and Part 2), ride the shuttle bus up, or park at one of the lots near the Fortezza. (When you’re done there, you can still do Part 1—backwards—on the way back down.)
This guided stroll takes you up through Montepulciano’s commercial (and touristy) gamut 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 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 “passaggio segreto” on the left. While Montepulciano did have secret passages tunneled through the rock beneath it (handy during times of siege), this particular passage—right next to the city’s front door—was probably no segreto...though it works great for selling salami.
Walk directly through the Porta al Prato, looking 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. 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 Colonna del 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.
The column is also the starting point for Montepulciano’s masochistic tradition, the Bravio delle Botti, held on the last Sunday of August, in which each local contrada (neighborhood) 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 daypack. Do you see colorful flags lining the street? If so, you’ll notice you’re in the Gracciano contrada, symbolized by the green, black, and yellow lion. Notice how the flags change with the neighborhood as you continue through town.
A few steps up, on the right (at #91, with stylized lion heads), 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 palazzi—Florentine nobility favored Montepulciano as a breezy and relaxed place for a secondary residence. 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 #73 (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 their alphabets: The “backwards” Etruscan letters (they read from right to left) resemble Greek. Many of the fragments show a circle flanked by a pair of inward-facing semicircular designs. This symbol represents the libation cup used for drinking at an Etruscan banquet.
At the top of the block on the right is the Church of Sant’Agostino. Its late-Gothic facade features a terra-cotta sculpture group by the architect Michelozzo, a favorite of the Medicis in Florence. The interior is a clean, serene, white-and-beige space.
Hike up a few more steps, 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 commedia dell’arte theatrical tradition.
Continuing up, at the alimentari on the right (at #23), notice the classic old sign advertising milk, butter, margarine, and olive and canola oil. Keep on going (imagine pushing a barrel now), and bear right with the street under another sturdy gateway—indicating that this city grew in concentric circles. Passing through the gate, you’ll run into a loggia (with the Florentine Medici seal—a shield with balls).
Facing the loggia, veer 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.
Again, notice the fine and ever-bulkier palaces. On the left, a tiny courtyard makes it easier to appreciate the grandiosity of the next palace, now home to UBI Banca. By the way, the stone scrolls under the window are a design element called a “kneeling window”—created by Michelangelo and a popular decorative element in High Renaissance and Mannerist architecture. You’ll see kneeling windows all over town.
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, loaner newspapers on long sticks, and a little terrace with spectacular views.
A bit farther up, 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 vistas. Many of these side lanes are spanned by brick arches, allowing centuries-old buildings to lean on each other for support rather than toppling over—a fitting metaphor for the tight-knit communities that vitalize small Italian towns.
Continuing up, notice more kneeling windows. The next church on the left, the Jesuit Church of Gesù, is worth a look. Its interior is elliptical in shape and full of 3-D illusions (the side chapels and the cupola are all painted on flat surfaces). Soon the street levels out—enjoy this nice, lazy, easy stretch, with interesting shops and artisan workshops (such as the mosaics studio at #14, on the right). A few short blocks farther, across from #64, a lane leads to a charming terrace with a commanding view of the Tuscan countryside.
The Mazzetti copper shop (#64) is crammed full of decorative and practical items. The production of hand-hammered copper vessels like these is a dying art; in this shop, you can see works by Cesare, who makes them in his workshop just up the street.
Continuing steeply uphill will take you to the main square. At the bend just before the square, Cesare’s buddy Adamo loves to introduce travelers to Montepulciano’s fine wines at the Contucci Cantina (described later). Visit Cesare and Adamo now, or head up to the square for Part 2 of this walk.
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. The medieval Palazzo Comunale, or town hall, resembles Florence’s Palazzo Vecchio—yet another reminder that Florence dominated Montepulciano in the 15th and 16th centuries. The crenellations along the roof were never intended to hide soldiers—they just symbolize power. 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. You’ll see the one-time building of the courts, behind the well (Palazzo del Capitano); the noble Palazzo Tarugi, a Renaissance-arcaded confection (with a public loggia at ground level and a private loggia—now enclosed—directly above); 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.
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 grilles to keep animals from contaminating the water supply, and its decorative top: the Medici coat of arms flanked by lions (representing Florence) dwarfing griffins (representing Montepulciano).
Climbing the town hall’s tower rewards you with a windblown but commanding panorama from the terrace below the clock. Go into the Palazzo Comunale, head up the stairs to your left, and pay on the second floor. You can pay to go just as far as the terrace, at the base of the tower (€2.50, 71 stairs, or ride the elevator halfway up); or pay more to go all the way to the top, twisting up extremely narrow brick steps past the antiquated bell-ringing mechanism (€5, 76 additional stairs). If you don’t mind the claustrophobic climb, it’s worth paying extra to reach the very top, from where you can see all the way to Pienza (look just to the right of San Biagio Church; tower open daily May-Oct 10:00-18:00, closed in winter).The street to the left as you face the tower leads to the Fortezza.
To the Church of San Francesco and Views: From the main square, a short, mostly level walk leads to a fine viewpoint. You could head 200 yards straight 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 down Via Talosa, the narrow lane between the two palaces in the corner of the square. Pause at the recommended 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. Across the street is the recommended Cantina della Talosa wine cellar—imagine the wine caves below your feet.
Follow this lane as it bends left, and eventually you’ll pop out just below the main square, a few doors from the recommended De’ Ricci Cantine wine cellar. Turn right and head down toward the church. Just before #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.
While tourists have romanticized notions of the “Tuscan” landscape, there is a surprisingly wide variety of landforms in the region. Never having been crushed by a glacier, Tuscany is anything but flat. Its hills and mountains are made up of different substances, each suited to very different types of cultivation.
The Chianti region (between Florence and Siena) is rough and rocky, with an inhospitable soil that challenges grape vines to survive while coaxing them to produce excellent wine grapes.
South of Siena, the soil switches from rock to clay, silt, and sand. The region called the Crete Senesi is the perfectly described “Sienese Clay Hills.” Looking out from a breezy viewpoint, you can easily visualize how these clay hills were once at the bottom of the sea floor. The soil here is perfect for truffles and for vast fields of wheat, sun-yellow rapeseed (for canola oil), and periodically fava beans (to add nitrogen to the soil). In the spring and summer, the Crete Senesi is blanketed with brightly colorful crops and flowers in spring and summer, but by the fall, after the harvest, it’s brown, dusty, and desolate. Within the Crete Senesi, you can distinguish two types of hills shaped by erosion: smooth, rounded biancane and pointy, jagged calanchi.
The area around Montepulciano and Montalcino is more varied, with rocky protuberances that break up the undulating clay hills and provide a suitable home for wine grapes. Even farther south is the Val d’Orcia. This valley of the Orcia River is similar to the Crete Senesi, but has fewer rocks and jagged calanchi. Montepulciano sits in a unique position between the Val d’Orcia and the much flatter Val di Chiana (through which Italy’s main north-south expressway runs).
You’ll see many hot springs in this part of Tuscany, as well as town names with the word Terme (for “spa” or “hot spring”) or Bagno (“bath”). These generally occur where clay meets rock: Water moving through the clay encounters a barrier and gets trapped. A byproduct of these mineral springs is the limestone called travertine, explaining the quarries you may see around spa towns.
Across the street and a few steps farther (on the right), you hit a viewpoint. From here, it’s easy to appreciate 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 downhill, then uphill, into the big parking lot in front of the Church of San Francesco. Head out to the overlook 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. You can also see Montepulciano’s most impressive church, San Biagio—well-worth a visit for drivers or hikers.
From here, you can head back up to the main square, or drop into one of my recommended cantinas to spelunk their wine cellars.
For me, Montepulciano’s best “experiences” are personal: dropping in on Adamo, the winemaker at Contucci Cantina, and Cesare, the coppersmith at Ramaio Cesare. Both 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 here since 1961 and welcomes tourists into the cellar. While at the palace, you may meet Andrea or Ginevra Contucci, who love to share their family’s products with the public. Adamo and the Contuccis usually have a half-dozen bottles open, and at busy times, other members of their staff are likely to speak English.
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.
Cost and Hours: Free drop-in tasting, free cellar tour upon request, daily 10:00-18:30, shorter hours off-season, Piazza Grande 13, tel. 0578-757-006, www.contucci.it.
Cesare 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, Cesare (CHEH-zah-ray) is 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. Peruse his tools: a giant Road Runner-style anvil, wooden hammers, and stencils dating from 1857 that have been passed down from his grandfather and father. 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’s justifiable pride in his vocation evokes the hardworking, highly skilled craft guilds that once dominated small-town Italy.
Cost and Hours: Demonstration and museum are free, Cesare is generally in his workshop Mon-Sat 9:00-12:30 & 14:30-18:30, closed Sun, 50 yards steeply downhill from the Contucci Cantina at Via del Teatro 4, tel. 0578-758-753, www.rameria.com. Cesare’s delightful shop is on the main drag, a block below, 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, where, amid the fairly austere interior, you’ll be rewarded with some fine art. A beautiful blue-and-white, glazed terra-cotta Altar of the Lilies by Andrea della Robbia is behind the baptismal font (on the left as you enter). The high altar, with a top like a pine forest, features a luminous, late-Gothic 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.
Cost and Hours: Free, daily 8:30-18:30.
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, down, down a spiral staircase—with rounded steps designed to go easy on fragile noble feet, and lined with rings held in place by tiny, finely crafted 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 into the cellars, natural stone seems to take over the brick. At the deepest point, you can peer into the atmospheric Etruscan cave, where a warren of corridors spins off from a filled-in well. Finally you wind up in the shop, where you’re welcome to taste a few wines (with some local cheese). Don’t miss their delightful dessert wine, vin santo.
Cost and Hours: First three tastings-free, two additional premium tastes-€5, €12-35 bottles, affordable shipping, daily 10:30-18:30, enter Palazzo Ricci at Via Ricci 11—look for signs for Cantine de’ Ricci, tel. 0578-757-166, www.cantinadericci.it, Enrico.
This historic cellar, which goes down and down to an Etruscan tomb at the bottom, ages a well-respected wine. With a passion and love of their craft, Andrea and Cristian Pepi give enthusiastic tours and tastings. While you can drop by for a free sample, it’s also possible to call ahead to book a complete tour and tasting (€20, including five wines to taste and light food).
Cost and Hours: Free tasting, daily March-Oct 10:30-19:00, shorter hours off-season, a block off Piazza Grande at Via Talosa 8, tel. 0578-757-929, www.talosa.it.
The church is just west of town, at the base of Montepulciano’s hill, down a picturesque cypress-lined driveway. Often called the “Temple of San Biagio” because of its Greek-cross style, this church—designed by Antonio da Sangallo the Elder and built of locally quarried travertine—feels like Renaissance perfection. If the church is empty, experiment worshipfully with the marvelous acoustics. Consider a picnic or snooze on the grass in back, with fine vistas over the Chiana Valley. The recommended La Grotta restaurant is across the street from the church.
Cost and Hours: €3.50, includes 20-minute audioguide; daily 10:00-18:00, longer hours in summer, shorter hours in winter.
$$$$ La Locanda di San Francesco is overpriced but luxurious, with four stylish view rooms over a classy wine bar on a quiet square at Montepulciano’s summit (closed Nov-Easter, air-con, free parking nearby, Piazza San Francesco 5, tel. 0578-758-725, www.locandasanfrancesco.it, info@locandasanfrancesco.it, Luca).
$$ Mueblè il Riccio (“The Hedgehog”) is medieval-elegant, with 10 modern and spotless rooms, an awesome roof terrace, and friendly owners. Five are newer “superior” rooms with grand views across the Tuscan valleys (family rooms, breakfast extra, air-con, 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). Charming Gió and his son Iacopo give tours of the countryside (€50/hour) in one of their classic Italian cars.
$$ Albergo Duomo is big, modern, and nondescript, with 13 simple but dignified rooms (with small bathrooms) and a comfortable lounge downstairs. With a handy location just a few steps from the main square, it’s at the very top of town, with free private parking nearby (RS%—use code “Steves,” family rooms, elevator, air-con in some rooms—extra charge, Via di San Donato 14, tel. 0578-757-473, www.albergoduomo.it, albergoduomo@libero.it, Simone).
$$ Vicolo dell’Oste B&B, just off the main drag halfway up through town, has five family-friendly modern rooms. Some are like tiny apartments (RS%, includes breakfast at nearby café, 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).
$ Camere Bellavista has 10 tidy rooms. True to its name, the rooms have fine views—though some are better than others. Room 6 has a view terrace worth reserving; there’s also one economy room without a view (cash only, no breakfast, lots of stairs with no elevator, reception not always staffed—call before arriving or ring bell, Via Ricci 25, mobile 347-823-2314, www.camerebellavista.it, info@camerebellavista.it, Gabriella and Alessio speak just enough English).
Unless otherwise noted, these places are all open for lunch (about 12:30-14:30) and again for dinner (about 19:30-22:00).
$$$ Osteria dell’Acquacheta is a carnivore’s dream come true, beloved among locals for its beef steaks. Its long, narrow room is jammed with shared tables and tight, family-style seating, with an open fire in back and a big hunk of red beef lying on the counter like a corpse on a gurney. Giulio and his wife, Chiara, run a fun-loving but tight ship—posing with slabs of red meat yet embracing decades of trattoria tradition (you’ll get one glass to use alternately for wine and water). Steaks are sold by weight (€32/kilo). Typically, two people split a 1.6-kilo steak (that’s 3.5 pounds; the smallest they’ll cook is 1.2 kilos). They also serve hearty pastas and salads and a fine house wine (or bring your own wine for a tiny corkage fee, reservations required; seatings generally at 12:30, 14:30, 19:30, and 21:30 only; closed Tue and unpredictably on other days; Via del Teatro 22, tel. 0578-717-086, www.acquacheta.eu).
$$ Osteria del Conte, an attractive but humble family-run bistro, offers cooking like your Italian mom’s. While the interior is very simple, they also have outdoor tables on a stony street at the top of the historic center (closed Mon, Via San Donato 19, tel. 0578-756-062).
$$ Le Pentolaccia is a small, family-run restaurant about two-thirds of the way up the main drag. With both indoor and outdoor seating, they make tasty traditional Tuscan dishes as well as daily fish specials. Cristiana serves, and husband-and-wife team Jacobo and Alessia stir up a storm in the kitchen (closed Thu, Corso 86, tel. 0578-757-582).
$$ Ai Quattro Venti is right on Piazza Grande, with a simple dining room and outdoor tables on the square. It offers reasonable portions of unfussy Tuscan food in an unpretentious setting. Try their own organic olive oil and wine (closed Thu, next to City Hall on Piazza Grande, tel. 0578-717-231, Chiara).
Wine Bar/Bistro: With a terrace on a tranquil square in front of the Church of San Francesco, $ E Lucevan le Stelle (part of La Locanda di San Francesco) is a fine place to nurse a glass of local wine (also pastas, salads, and soups; daily 12:00-24:00, closed Nov-Easter, Piazza San Francesco 5, tel. 0578-758-725, Luca).
Gelato: For the best gelato in town, look for Sgarbi Gelato Natura, near the bottom of the main drag. Owner Nicola makes his gelato fresh every morning, using locally sourced ingredients from producers he knows personally. The gelato is ready around 13:00—and when it’s gone, it’s gone (daily 11:00-20:00, Corso 50; also runs Buon Gusto in Pienza).
Just Outside Montepulciano: Facing San Biagio Church (at the base of Montepulciano’s hill, and described earlier), $$$ La Grotta has an excellent reputation for elevated Tuscan cuisine in a sophisticated, dressy setting. Reservations are recommended (Thu-Tue 12:30-14:15 & 19:30-22:00, closed Wed, Via di San Biagio 15, tel. 0578-757-479, www.lagrottamontepulciano.it).
Near Montepulciano: Skim this chapter for recommendations, and consider combining dinner with a scenic joyride. Good choices include Ristorante Daria in Monticchiello (here) and The Isabella Experience’s dinners near Castelmuzio (here).
Get bus schedules at the TI or the bus station on Piazza Pietro Nenni, which seems to double as the town hangout, with a lively bar and locals chatting inside. In fact, there’s no real ticket window—buy your tickets at the bar. Check www.tiemmespa.it for schedules.
By Bus to: Florence (1/day departs in the wee hours, 2/week additional departures a bit later in the morning, 2 hours, LFI bus, www.lfi.it; or take a bus to Chiusi to catch a train—see below), Siena (6-7/day, none on Sun, 1.5 hours, also possible to change here for Florence express bus), Pienza (8/day, 30 minutes), Montalcino (3-4/day, none Sun, change in Torrenieri, 1 hour; or consider a taxi—see below).
By Train: Trains are impractical here; the Montepulciano train station, five miles from town and connected by a 15-minute bus ride, has only milk-run trains (but could be useful for reaching Siena on a Sunday, when buses are scarce—get details at the TI). More convenient, consider riding the hourly bus 50 minutes to the town of Chiusi, which is on the main Florence-Rome rail line.
Taxi Alternatives: As the Montalcino bus connection is infrequent and complicated, consider hiring a taxi (about €70; see contact info under “Helpful Hints,” earlier).
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 into a city fit for a pope, 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.
Pienza’s architectural focal point is its main 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 well under an hour. Pienza is situated on a relatively flat plateau rather than the steep pinnacle of more dramatic towns like Montepulciano and Montalcino. (This is a plus for visitors with limited mobility, who find basically level Pienza easy to explore.)
Tourists flood Pienza on weekends and in peak season, and authentic local shops are outnumbered by boutiques selling gifty packages of pecorino cheese and local wine. Restaurants here tend to be more expensive and less reliable than alternatives in the nearby countryside. For these reasons, Pienza is made to order as a stretch-your-legs break to enjoy the townscape and panoramas, but it’s not ideal for lingering overnight (though some excellent options exist just outside town; see “Countryside Accommodations,” earlier). For the best experience, visit late in the day, after the day-trippers have dispersed.
Nearly every shop sells the town’s specialty: pecorino, a pungent sheep’s cheese (you’ll smell it before you see it) that’s sometimes infused with other ingredients, such as truffles or cayenne pepper. Look on menus for warm pecorino (al forno or alla griglia), often topped with honey and pine nuts 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 skippable Diocesan Museum (Wed-Mon 10:30-18:30 except Sat-Sun 10:00-16:00 off-season, closed Tue year-round, Corso il Rossellino 30, tel. 0578-749-905). Ignore the Informaturista kiosk just outside the gate—it’s a private travel agency.
Arrival in Pienza: 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 pay 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) in front of the town gate, head up the left side of town and look for the parking turnoff on the left (closed Fri morning during market). Buses drop you just a couple of blocks from the town’s main entrance.
Helpful Hints: On Friday mornings, a market fills Piazza del Mercato, the main parking lot 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).
I’ve connected Pienza’s main sights with walking directions, which can serve as a handy little orientation to the town. You could do this stroll in 30 minutes, but entering some of the sights could extend your visit to a few hours.
• Begin in the little park just in front of the town (near the main roundabout and bus stop), called Piazza Dante Alighieri. Facing the town, go through the big, ornamental gateway on the right (which was destroyed in World War II, and rebuilt in 1955) and head up the main street...
This main drag—named for Bernardo Rossellino (1409-1464), the Renaissance architect who redesigned Pienza according to Pius’ orders—is jammed with touristy boutiques. While you won’t find great values, these shops are (like Pienza) cute and convenient.
As you stroll this street, step into one of the many cheese-and-salami shops. Take a deep whiff and survey the racks of pecorino cheese, made from sheep’s milk. There are three broad categories of pecorino: fresco (young, soft, and mild), medio (medium), and stagionato (hard, crumbly, and pungent). Consider stocking up at one of these shops for a pricey but memorable picnic; some shops may be willing to give you a free sample. Finocchiona is salami with fennel seeds. This was first popularized by wine traders, because fennel seeds make wine taste better. To this day, Italians use the word infinocchiare (“fennel-ize”) to mean “to trick.”
Farther along, watch for the Church of San Francesco on the right. It’s the only important building in town that dates from before the Pius II extreme makeover. Its humble facade, simple nave, wood-beamed ceiling, bits of 14th-century frescoes, and tranquil adjacent cloister have a charm that’s particularly peaceful in the 21st century. But this gloomy medieval style was exactly what Pius wanted to get away from.
• Continuing one more block, you’ll pop out at Pienza’s showcase square...
Pienza’s small main piazza gets high marks from architecture highbrows for its elegance and artistic unity. One day, Pope Pius II (who was born here) was traveling nearby with Leon Battista Alberti, one of the great architectural pioneers of the Renaissance. Proud to show off his hometown, Pius brought Alberti here...but, seeing it through the eyes of his esteemed companion, he was filled with embarrassment rather than pride at its primitive architectural style. Pius decided this just wouldn’t do, and commissioned Alberti’s student Bernardo Rossellino to remake the town into a Renaissance masterpiece.
Rossellino designed the piazza and surrounding buildings to form an “outdoor room.” Everything is perfectly planned and plotted. Do a clockwise spin to check out the buildings that face the square, starting with the Duomo (which we’ll enter soon). High up on the facade is one of many examples you’ll spot around town of the Piccolomini family crest: five half-moons, advertising the number of crusades that his family funded.
To the right of the Duomo is the Piccolomini family palace, now a tourable museum. Notice that the grid lines in the square’s pavement continue all the way up the sides of this building, creating a Renaissance cube. Upon closer inspection, you can see that the windows at the far end of the building are a bit narrower—creating an optical illusion that the palace is longer than it actually is.
Looking farther right, you’ll see City Hall (Palazzo Comunale), with a Renaissance facade and a fine loggia (to match the square) but a 13th-century bell tower that’s shorter than the church’s tower. That’s unusual here in civic-minded Tuscany, where municipal towers usually trumpet the importance of town over Church.
Looking up the lane to the left of City Hall, notice the cantilevered upper floors of the characteristic old houses—a reminder that, while Pienza appears Renaissance on the surface, much of that sheen was added later to fit Pius’ vision. Turning right again, see the Bishop’s Palace, also called the Borgia Palace (now housing the TI and the skippable Diocesan Museum). Pius envisioned his remade hometown as a sort of “summer Vatican,” where an entourage of VIPs would spend time—and each one needed their own palace. The Borgia clan, who built this palace, produced one of the most controversial popes of that age, Alexander VI, who ascended to the papacy a few decades after Pius II.
Finally, between the Bishop’s Palace and the Duomo, a lane leads to the best view terrace in town.
• Before going there, take the time to tour whichever of the square’s sights interest you:
The cathedral’s classic, symmetrical Renaissance facade (1462) dominates Piazza Pio II. The interior, bathed in light, is an illuminating encapsulation of Pius II’s architectural philosophy (free, generally daily 7:00-13:00 & 14:30-19:00). Pius envisioned this church as an antidote to dark, claustrophobic medieval churches, like the Church of San Francesco we saw earlier. Instead, this was to be a “house of glass,” representing the cultural enlightenment that came with the Renaissance. As you walk to the end of the church, notice the cracks in the apse walls and floor, and get seasick behind the main altar. The church’s cliff-hanging position bathes the interior in light, but the building also feels as though it could break in half if you jumped up and down.
This palace, the home of Pius II and the Piccolomini family (until 1962), is not quite the interesting slice of 15th-century aristocratic life that it could be (I’d like to know more about the pope’s toilet). But 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 courtyard. In Renaissance times, most buildings were covered with elaborate paintings like those you’ll see here.
Cost and Hours: €7, includes dry audioguide, Wed-Mon 10:00-18:30, until 16:00 off-season, closed Tue, Piazza Pio II 2, tel. 0578-748-392, www.palazzopiccolominipienza.it.
• When you’re done sightseeing, head up the little lane to the left of the church facade. This takes you out to a grand pedestrian-only...
Stroll this panoramic promenade to the end, taking in views over the Tuscan countryside and, in the distance, Monte Amiata, the largest mountain in southern Tuscany. Retrace your steps and exit the viewpoint down the first alley, Via del’Amore—the original Lover’s Lane—which leads back to the main drag, Corso il Rossellino.
• Turn right and stroll along this street one block, then turn left up Via Sant’Andrea. Soon you’ll run into Via delle Case Nuove, a charming row of homes with staggered doorways. These “new houses” (as the street’s name means) were built by the pope to house the poor. Just to the left (as you face these houses) is Pienza’s “destination” gelateria, the recommended Buon Gusto.
This classic Romanesque parish church (pieve), hugging the slope just below Pienza, is a reminder of a much earlier, rougher, simpler time (before Pope Pius II). This was one of the medieval pilgrimage stops on the Via Francigena.
The round, eighth-century watchtower guards the squat, 11th-century church, whose unusual exterior iconography is from an age when the pagan roots of early Christianity were vivid and unmistakable—especially here, deep in the countryside. The church is decorated not with saints and angels, but with geometric and flowery motifs as well as mysterious creatures. Inside, near the entrance on the right, look for the font that was used to baptize the infant who would grow up to be Pope Pius II.
Getting There: On foot from Pienza, it’s a steep 10-minute downhill walk (as you exit Pienza into the main park, look to your left for pieve di Corsignano signs). Drivers loop around the far end of town (as described on my Heart of Tuscany drive, later); just before the road bends sharply left and twists downhill, watch for the pieve di Corsignano signs on the right (free parking).
$$$ La Bandita Townhouse Caffè offers a break from Tuscan rusticity, focusing instead on tempting modern Italian cuisine (such as spring pea soup or spicy Chianina beef tartare). Diners watch the chef work in his open kitchen (dinner nightly 19:30-22:00, lunch Tue-Sun 12:30-15:00, indoor/outdoor seating, Corso il Rossellino 111, easier to enter around the corner on Via Sant’Andrea, tel. 0578-749-005).
$$ Trattoria Latte di Luna, with outdoor tables filling a delightful little square, is the more traditional choice. While the food can be hit-or-miss, locals swear by their specialty, roast suckling pig (maialino da latte arrosto). Run by friendly Roberto with Delfina in the kitchen, the dining room features an ancient well and sits on top of Etruscan tunnels (Wed-Mon 12:10-15:30 & 19:10-22:00, closed Tue, at the far end of town at Via San Carlo 2, tel. 0578-748-606).
Quick Lunch: For something cheap, characteristic, and fast, just grab a tasty $ porchetta sandwich at the little no-name shop 30 yards off the main square (at Corso il Rossellino 81) and munch it under the loggia or at the viewpoint (daily 8:00-20:00).
Top-Quality Gelato: Small batches and quality ingredients are on the menu at Buon Gusto. Nicola creates fun original flavors, which can include carrot-ginger, creamy basil, or kiwi-spinach. The gelato is typically ready by around 13:30—just in time for after lunch. They also do fresh-pressed juices and smoothies (daily 11:00-20:00, until 22:00 in summer, closed off-season, Via delle Case Nuove 26, mobile 335-704-9165). Nicola also runs Sgarbi Gelato Natura in Montepulciano.
Cocktails with Nibbles: Pienza isn’t much for nightlife, but for a cocktail in a somewhat local-feeling setting, drop in at Idyllium—a hip cocktail bar serving creative herb-infused drinks, light food, and outdoor seating facing grand Tuscan splendor (daily 11:00-late, from the main square, go down the little lane to the right of the church to Via Gozzante 67, tel. 0578-748-176).
Despite having more than its share of tourists, Pienza suffers from a lack of quality restaurants. These options are all within about a 15-minute drive and offer a more memorable meal than places in town. To locate Castelmuzio, see the “Heart of Tuscany” map on here.
Just Outside Castelmuzio: For an excellent meal and a memorable activity, consider dinner at the fine $$$$ restaurant at La Moscadella, run by The Isabella Experience (recommended in “Countryside Accommodations,” earlier in this chapter). A limited number of tables are available to nonguests who book ahead. One evening there may be a truffle hunt through the woods followed by a truffle dinner; the next, an olive oil tasting session may be followed by a meal with olive oil pairings. Expect to pay around €60 per person, including the premeal experience, a four-course meal, aperitivo, and wine; the truffle hunt/meal is €120/person (reservations required, usually offered Fri-Tue, veggie alternatives available, tel. 0577-665-516, info@theisabellaexperience.com).
In Castelmuzio: To escape Pienza’s tourist crowds, drive about 15 minutes to the remote village of Castelmuzio. The hamlet’s lone restaurant, $$ Locanda di Casalmustia, is a cozy and typically uncrowded spot serving good local cuisine. Choose between sitting out on the stony lane or in a cute fresco-ceilinged dining room. While not quite a destination restaurant, it’s a good excuse to explore an untrampled hill town and enjoy sweeping views of the countryside (Tue-Sun 8:00-22:00, closed Mon, in the heart of the town at Piazza della Pieve 3, tel. 0577-665-166).
In Monticchiello: In the opposite direction, but about the same distance away is the excellent Ristorante Daria (see “Eating in Monticchiello,” later in this chapter; for location see the “Heart of Tuscany” drive map on here).
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.
From Pienza by Bus to: Siena (6/day, none on Sun, 1.5 hours), Montepulciano (8/day, 30 minutes), Montalcino (3-4/day, none Sun, change in Torrenieri, 60 minutes). Bus info: www.tiemmespa.it.
On a hill overlooking vineyards and valleys, Montalcino is famous for its delicious and pricey Brunello di Montalcino red wines. It’s a pleasant, low-impact town crawling with wine-loving tourists and a smattering of classy shops, but little sightseeing. Everyone touring this area seems to be relaxed and in an easy groove...as if enjoying a little wine buzz.
While today it’s all about the wine, Montalcino (mohn-tahl-CHEE-noh) has an incredibly long history—human settlement here dates back some 200,000 years. That’s because Montalcino has a unique setting, with protective caves and a freshwater spring high atop a rocky pinnacle—a highly desirable position for Neolithic humans. For much of its long history, Montalcino was a veritable fortress, perched high overlooking the valley below and its Via Francigena pilgrim route.
Flash forward to the Middle Ages, when Montalcino 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 Montalcinesi to join their side by forcing them to collect corpses and sleep one night in the bloody, Florentine-strewn battlefield. Later, the Montalcinesi took in Sienese refugees. To this day, in gratitude for their support, the Sienese invite the Montalcinesi to lead the parade that kicks off Siena’s Palio celebrations.
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. (For more on this wine, see the “Wines in the Region” sidebar later in this chapter). Montalcino provides a handy springboard for exploring the surrounding wine region.
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, sells bus tickets; can call ahead to book a visit at a countryside winery (small fee); and has information on taxis to nearby towns, abbeys, and monasteries (daily 10:00-13:00 & 14:00-17:50, tel. 0577-849-331, www.prolocomontalcino.com).
Arrival in Montalcino: For a short visit here by car, drivers should head to the pay lot in Piazzale Fortezza. Skirt around the fortress, take the first right (just past a little park), and follow signs to parking and Fortezza (€1.60/hour, free 20:00-8:00). Or, if you don’t mind a short climb, park for free below the fortress: At the roundabout with the ugly statue, take the small downhill lane into the big lower parking lot (blue lines mean that you have to pay, but the lower-level unmarked spots are always free). If these lots are full, follow the town’s western wall toward the Madonna del Soccorso church and a long pay lot.
The bus stop is on Piazza Cavour, a little park about 300 yards from the town center. From here, simply follow the main drag, Via Mazzini, straight up into town. While Montalcino has no official baggage storage, a few shops are willing to hold on to one or two bags on a short-term basis; ask at the TI.
Helpful Hints: Friday is market day (7:00-13:00) on Viale della Libertà, near the Fortezza.
All roads in tiny Montalcino lead to the main square, Piazza del Popolo (“People’s Square”).
City Hall was the fortified seat of government. It’s decorated with 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 balls, or pills) dominates the others. The one-handed clock was the norm until 200 years ago.
For five centuries, the large arcaded loggia (on your left as you face the clock tower) hosted the town market.
For some wine-centric whimsy, go up around the right side of the City Hall and find a series of plaques (each designed by a different artist), which show off the annual rating of the Brunello harvest from two to five stars—important, as wine is the lifeblood of the local economy. And, of course, it’s fun to simply observe the passeggiata—these days mostly a parade of tourists here for the wine.
Back on the square, notice the grand café (on the right as you face the clock tower). Since 1888, 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.
While technically two museums in one (archaeology and medieval and modern art), and surprisingly big and modern for this little town, Montalcino’s lone museum ranks only as a decent bad-weather activity. The cellar is filled with interesting artifacts dating back as far as—gulp—200,000 BC. 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 century). The ground floor is best, with a large collection of crucifixes and the museum’s highlights, a glazed terra-cotta altarpiece and a statue of St. Sebastian, both by Andrea della Robbia.
Cost and Hours: €4.50, €6 combo-ticket with Fortezza, Tue-Sun 10:00-13:00 & 14:00-17:30, closed Mon, Via Ricasoli 31, to the right of Sant’Agostino Church, tel. 0577-846-014.
This 14th-century fort, built under Sienese rule, is now little more than an empty shell (with a popular wine bar—see below). It was built to defend against catapults and arrows, but the cannon was invented shortly thereafter. You can still see pockmarks from cannonballs fired here in 1553 on the outer wall (facing away from the town), but the fort withstood the attack. You’re welcome to enter the big, open courtyard (with WCs out the far end), or just enjoy a picnic in the park surrounding the fort, but if you want to climb the ramparts for a panoramic view, you’ll have to pay.
Cost and Hours: €4, €6 combo-ticket with Montalcino Museums, enter though wine bar, daily 9:00-20:00, off-season 10:00-18:00.
If you won’t make it to the wineries outside Montalcino, simply visit a wine bar in town, where you can comfortably taste a variety of vintages before stumbling safely back to your hotel. This is also a great strategy for Sundays, when many countryside wineries are closed.
Caffè Fiaschetteria Italiana, a classic 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. But if you’re not seeking venerable ambience and sidewalk seating, you can taste wine more affordably elsewhere (Brunellos by the glass, light snacks and plates; same prices inside, outside, or in back room; daily 7:30-23:00, Piazza del Popolo 6, tel. 0577-849-043).
Enoteca di Piazza—part of a chain of wine shops with mechanical dispensers—is a fun way to efficiently taste a variety of different wines in a forgettable setting. Here’s how it works: A “drink card” (like a debit card) keeps track of the samples you take, for which you’ll pay from €1 to €9 apiece. They stock 100 different wines, including some whites—rare in this town. This is a good spot to assemble a box of wine from different local producers to ship home. Their small restaurant lets you enjoy your drink card with local dishes (daily 9:00-20:00, near Piazza del Popolo at Via Matteotti 43, tel. 0577-848-104, www.enotecadipiazza.com).
Enoteca la Fortezza di Montalcino offers a chance to taste top-end wines by the glass, each with an English explanation. While the prices are a bit higher than other enoteche in town, the medieval setting inside Montalcino’s fort is popular with tourists. Spoil yourself with Brunello in the cozy enoteca or at an outdoor table in the fortress courtyard (tastings start at €15 for 3 wines and go up from there; pricey full meals and sampler plates of cheeses, salumi, honeys, and olive oil available; daily 9:00-20:00, until 18:00 Nov-March, inside the Fortezza, tel. 0577-849-211).
The countryside around Montalcino is littered with wineries, some of which offer tastings. As Brunello is the poshest of Italian wines, these wineries feel a bit upscale, and most require an advance reservation. It’s a simple process (just call and arrange a time), and they’ll delight in showing you around. Tours generally last 45-60 minutes, cost €10-15 per person, and conclude with a tasting of three or four wines. The Montalcino TI can give you a list of more than 150 regional wineries and will call ahead for you. Or check with the vintners’ consortium (tel. 0577-848-246, www.consorziobrunellodimontalcino.it). Many wineries are closed on Sunday, so check before heading out. For locations of the wineries listed below, see the “Heart of Tuscany” map, near the beginning of the chapter.
This region has two well-respected red wines, each centered on a specific town: Montepulciano is known for its Vino Nobile, while Montalcino is famous for its Brunello. In each wine, the predominant grape is a clone of sangiovese (Tuscany’s main red wine grape).
Vino Nobile di Montepulciano (“noble wine of Montepulciano”) is a high-quality, dry ruby red, made mostly with the Prugnolo Gentile variety of sangiovese (70 percent), plus other varieties including Mammolo (30 percent). Aged two years (or three for a riserva)—one year of which must be in oak casks—it pairs well with meat, especially roasted lamb with rosemary, rabbit or boar ragù over pasta, grilled portobello mushrooms, and local cheeses like pecorino. Several large wineries produce and age their Vino Nobile in the sprawling cellars beneath the town of Montepulciano. Three of these are fun and easy to tour (see “Sights and Experiences in Montepulciano” on here). The oldest red wine in Tuscany, Vino Nobile has been produced since the late 1500s.
Brunello di Montalcino (“the little brown one of Montalcino”—named for the color of the grapes before harvest) is even more highly regarded and ranks among Italy’s finest and most expensive wines. Made from 100 percent Sangiovese Grosso (a.k.a. Brunello) grapes, it’s smooth, dry, and aged for a minimum of two years in wood casks, plus an additional four months in the bottle. Riserva wines are aged an additional year. Brunello is designed to cellar for 10 years or longer—but who can wait? It pairs well with the local cuisine, but the perfect match is the fine Chianina beef.
Today, there are around 240 mostly small producers of Brunello in the Montalcino region; I’ve recommended just a few, which I find fun and accessible. A simpler option is to sample a few different wines at one of the good wine bars in Montalcino (see here).
You’ll also see Rosso di Montalcino (a younger version of Brunello), which is aged for one year. This “poor man’s Brunello” is very good, at half the price.
If you lack a car (or don’t want to drive), you can take a tour on the Brunello Wine Bus, which laces together visits to four wineries, with a lunch break in the middle, either on your own in Montalcino or at a farmhouse for an extra fee (€140; tours run March-Nov Tue and Thu only; departs at 10:00, returns at 19:00; tours leave from their office, or they will pick you up within 3 miles—5 km—of Montalcino; half-day tours available Tue and Thu-Sat for €75; Via Circonvallazione 3, tel. 0577-846-021, www.winetravelsforyou.com, info@winetravelsforyou.com).
If you’re paying for a wine tasting, you aren’t obligated to buy. But if a winery is doing a small tasting just for you, they’re hoping you’ll buy a bottle or two.
This charmingly low-key, family-run winery is a short drive outside of Montalcino, perched on a grand view terrace overlooking the famous Biondi Santi winery (where Brunello was invented). Maurizio, Elisa, and Valentina offer tours and tastings in this scenic setting. They enjoy explaining how their logo—the cuckoo (kukula) bird—was inspired by their chatty grandfather (reserve ahead, €13 for 3 tastes plus tour, €20 includes tasting and lunch, €20-40 bottles, closed Sun, mobile 349-093-2167, www.brunellotornesi.it). Leaving Montalcino, at the main roundabout, go uphill toward Grosetto, then watch for the brown Benducce sign on the left (just before the road bends right). Tornesi is a short drive down this gravel road, on the left.
Perched high above the Romanesque Sant’Antimo Abbey, overlooking sprawling vineyards, this winery (owned by the Illy coffee company) is big and glitzy—yet doesn’t feel as corporate or soulless as some of the bigger players (€17-36 bottles, reserve ahead, Podere Loreto e San Pio, tel. 0577-835-681, www.mastrojanni.com). To reach it, head up into the town of Castelnuovo dell’Abate (just above Sant’Antimo Abbey), bear left at the Bassomondo restaurant, and continue up along the gravel road (enjoying vineyard and abbey views).
This well-respected, family-run vineyard has a classy tasting room/enoteca and an outdoor view terrace. If you’re just dropping in, belly up to the wine bar for two or three free tastes. Or reserve ahead for a more formal tasting of top-quality wines for €10-25, which includes a tour of the cellar (April-Oct Mon-Fri 9:00-19:00, Sat 10:30-18:30, closed Sun; down a back lane near Sant’Antimo Abbey—head toward Castelnuovo dell’Abate but go right before entering that town, following signs toward Sant’Angelo in Colle, tel. 0577-835-616, www.ciaccipiccolomini.com, visite@ciaccipiccolomini.com).
Much bigger and glossier than the other recommended wineries, Banfi is one of the largest producers in the area. Despite its size, the estate is charming, set in a castle located in a picturesque corner southwest of Sant’Antimo. This is a good option for Sundays, when other places are closed, or for a spontaneous drop-in tasting at the winery’s enoteca (tastings start at €12, daily 10:00-19:30, until 18:00 Nov-March, tours available on request, tel. 055-877-500, www.castellobanfiilborgo.com, enoteca@banfi.it). You’ll find Banfi about 20 minutes south of Montalcino; follow SP-14 to Borgo Santa Rita and cut back north, following signs to Poggio alle Mura.
Elegant and stately, Altesino owns perhaps the most stunning location of all, just off the back road connecting Montalcino north to Buonconvento. You’ll twist up on cypress-lined gravel lanes to this perch, which looks out over an expanse of vineyards with Montalcino hovering on the horizon (€15 for tour and basic tasting, daily, reserve ahead, Loc. Altesino 54, tel. 0577-806-208, www.altesino.it, info@altesino.it). You’ll find the turnoff for Altesino along the back road (SP-45) between Montalcino and Buonconvento.
On the outskirts of Torrenieri, this is a quintessential family-run winery, with an emphasis on quality over quantity (only 20,000 bottles a year). They also produce excellent olive oil, prosciutto, and salami. Less picturesque and much more rustic than the other wineries listed here, a tour at Santa Giulia is a Back Door experience. Call to find a time that fits their schedule; around lunchtime, you can arrange a “Zero Kilometer” tasting, with farm-fresh cold cuts, cheese, and bruschetta for €20; add pasta and dessert for €15 more (€20 for 3 tastes and tour, 2-person minimum, €15-32 bottles, Loc. Santa Giulia 48, closed Sun, tel. 0577-834-270, www.santagiuliamontalcino.it, info@santagiuliamontalcino.it). From Torrenieri’s main intersection, follow the brown Via Francigena signs. After crossing the train tracks and a bridge, watch on the left to follow signs for Sasso di Sole, then Sta. Giulia; you’ll take gravel roads through farm fields to the winery.
$$$ Hotel Dei Capitani, at the end of town near the bus station, has plush public spaces, an inviting summertime pool, and a cliffside terrace offering plenty of reasons for lounging. About half the 29 rooms come with vast Tuscan views and are worth paying a bit extra for (request a view room when you reserve); the nonview rooms are bigger but face a somewhat noisy street (RS%, air-con, elevator, limited free parking—first come, first served, Via Lapini 6, tel. 0577-847-227, www.deicapitani.it, info@deicapitani.it).
$$ Palazzina Cesira (cheh-SHEE-rah), 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 (2-night minimum, air-con, free off-street parking, Via Soccorso Saloni 2, tel. 0577-846-055, www.montalcinoitaly.com, info@montalcinoitaly.com).
$ B&B da Idolina has four good rooms above a wine shop on the main street (includes basic breakfast in shared kitchen, check-in 15:00-19:00—call if arriving later, parking available, Via Mazzini 65, check in at the wine shop next door, tel. 0577-849-212, www.idolina1946.com, fulvia.soda@gmail.com, Fulvia).
$ Albergo Giardino, a great value, has nine big rooms done in a modern-minimalist style, no public spaces, and a convenient location near the bus stop (RS%, no breakfast, Piazza Cavour 4, tel. 0577-848-257, mobile 320-404-4655, www.albergoilgiardino.it, info@albergoilgiardino.it, Roberto and dad Mario).
$$$ Re di Macchia is an invitingly intimate restaurant where Antonio serves up the big, hearty portions of Tuscan fare that Roberta cooks. Look for their seasonal menu and a fine Montalcino wine list (Fri-Wed 12:00-14:00 & 19:00-21:00, closed Thu, reservations strongly recommended, Via Soccorso Saloni 21, tel. 0577-846-116).
$$ Taverna del Grappolo Blu, tucked in a cellar down a picturesque staircase off the main drag, is serious about its wine, game, homemade pasta, and vegetarian options (reservations smart, daily 12:00-15:00 & 19:00-22:00, a few steps off Via Mazzini at Scale di Via Moglio 1, tel. 0577-847-150, www.grappoloblu.it, Luciano).
$$ Ristorante-Pizzeria San Giorgio is a homey trattoria/pizzeria with traditional decor and reasonable prices. It’s great for families and a reliable choice for a simple meal (daily 12:00-15:00 & 19:00-22:30, closed Tue off-season, Via Soccorso Saloni 10, tel. 0577-848-507, Mara).
Quick Bite: The $ pizza al taglio shop, right on Piazza del Popolo at #11, has both pizza slices and sandwiches that they can heat up for you—ask for scalda (daily 10:30-21:30).
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.
Montalcino is well connected to Siena; other bus connections are inconvenient but generally workable. Montalcino’s bus stop 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. Check schedules at the TI, at the bus station, or online (at www.tiemmespa.it). The nearest train station is a 30-minute bus ride away, in Buonconvento.
From Montalcino by Bus: For long-distance journeys, you’ll always start out on bus #114, which goes to Siena (6/day Mon-Sat, 4/day Sun, 1.5 hours). En route, this bus goes through Torrenieri (change for Pienza or Montepulciano, 3-4/day, none on Sun); from Torrenieri it’s 25 minutes to Pienza, 45 minutes to Montepulciano, then Buonconvento (where you can catch a train to Florence). You can also reach Florence by riding the bus to Siena, then taking the train from there. Since the Montepulciano bus connection is sporadic, consider hiring a taxi (about €70 one-way).
If you have just one day to connect the ultimate Tuscan towns and views, this is the loop I’d stitch together with a driving tour. In addition to larger towns (Montepulciano, Pienza) and smaller ones (Bagno Vignoni, Rocca d’Orcia), this loop drive, worth ▲▲▲, gives you a good look at the area called the Val d’Orcia (val DOR-chah), boasting some of the best scenery in Italy. Most of this journey is through velvety, gentle, rolling hillsides generously draped with vivid-green crops in the springtime, and a parched moonscape in the late summer and fall. This almost otherworldly smoothness constitutes many travelers’ notions of Tuscan perfection.
Planning Your Drive: If you’re in a rush and don’t linger in any of the towns, you could do this drive in a couple of hours. To hit the sights, explore the towns, and linger over a meal or a glass of wine, spread it out over an entire day. (You could even splice in a side trip to a Brunello winery for a tasting.) I’ve started and ended the clockwise loop in Montepulciano, but you could just as easily start and end in Pienza. If gardens are your thing, do this loop when La Foce Gardens are open.
Before leaving Montepulciano, consider dropping by the showpiece Renaissance San Biagio Church, which sits at the base of the town (watch for its long, level, tree-lined driveway exactly where you leave Montepulciano on the road toward Pienza—see “Sights and Experiences in Montepulciano,” earlier in this chapter).
To begin our loop, drive south, at first following signs to Chianciano Terme and Chiusi. Just 1 kilometer south of Montepulciano, watch on the right for the turnoff to Castelluccio and Monticchiello. Turn off here and zip along a pastoral back road for 5 kilometers. Pass the turnoff for Monticchiello on your right, and carry on straight ahead, as the road continues uphill and becomes gravel. Grinding your way up, watch on your right for the jagged Tuscan cliffs called calanchi. You’ll pop out at the T-intersection in front of the entrance to La Foce Gardens (from this intersection, parking and reception are 50 yards to the left—look for Loc. La Foce; learn more about the gardens later in this chapter).
From La Foce, head downhill tracking signs toward Siena and Roma. After a few hundred yards, watch on the left for the big gravel parking lot of the recommended Dopolavoro La Foce restaurant (across the street). From this lot, you have a fine view of one of the iconic cypress-lined driveways of Tuscany.
Continue downhill along this road for about 5 kilometers, through pristine farm fields, until you reach a major intersection, where you’ll turn right toward Pienza and Siena (on SP-53). Immersed in spectacular scenery, you’ll twist between giant cypresses for about 10 kilometers. This road parallels the region’s namesake Orcia River (“Val d’Orcia” means “Orcia River Valley”).
Take a moment to simply appreciate your surroundings. The famous Chianti region to the north (right) and the Brunello region to the west (straight ahead) are each a short drive away; in those places, the rocky soil is perfect for grapes. But here, instead of rocks, you’re surrounded by clay hills—once the floor of a prehistoric sea—that are ideal for cereal crops. Grains alternate every few years with a crop of fava beans, which help reintroduce nitrogen to the soil. It seems that every grassy hilltop is capped with a family farmhouse. Partway along this road, you’ll pass a turnoff (on the right) offering a speedy shortcut to Pienza, just 8 stunning kilometers away. But there’s so much more to see; I’d rather carry on with our loop.
The tower looming on the hill ahead of you is Rocca d’Orcia’s Tentennano Castle (described later). Nearing the end of the road, you’ll pass (on the left) the front door of an old farmhouse with oddly formidable crenellated towers, like a little castle in the field. This is Spedaletto Castle, built during the 12th century as a hospice for pilgrims walking the Via Francigena to Rome. Today it serves a similar purpose, as an agriturismo called La Grancia (“The Granary”), housing wayfarers like you.
When you reach a T-intersection with the main SR-2 highway, turn left (toward Roma), then immediately take the exit for Bagno Vignoni. To explore this fascinating medieval spa town—with its main square filled with a thermal-spring-fed pool—see “Heart of Tuscany Sights,” in the next section. To see the empty fortress at Rocca d’Orcia, stay on the SR-2 highway just 1 kilometer past Bagno Vignoni, then watch for the next turnoff.
From Bagno Vignoni, head north on SR-2 (toward San Quirico d’Orcia and Siena). After just 4 kilometers, in San Quirico d’Orcia, turn off onto the SP-146 road to Pienza, also marked for Chiusi, Chianciano Terme, and Montepulciano.
But before heading down that road, consider a few potential detours: First, if you won’t have time to delve deeply into Brunello wine country, now is a good time to side-trip to your choice of Brunello wineries; those I’ve recommended on here are all within about a 20- to 25-minute drive of San Quirico. Read the descriptions, take your pick, and ideally call ahead to reserve a tour and tasting. Another option is to zip into the town of Montalcino itself—an easy and well-signed 15-minute drive from San Quirico—and taste some local vintages at a wine bar there.
Back on the SP-146 road from San Quirico to Pienza, you enjoy one of the region’s most postcard-worthy stretches—with grand panoramas in both directions, including two more quintessential Tuscan scenes: the Chapel of Madonna di Vitaleta (after 2 kilometers, on the right); and a classic farmhouse with trees, just before Pienza (about 9 kilometers after San Quirico, on the left).
Finally, you’ll pull into Pienza, where you can park and tour the town using the information earlier in this chapter.
If you’re in a hurry or losing sunlight, just hop back on the main SP-146 road for the 12-kilometer straight shot back to Montepulciano (enjoying some pullouts on the left with fine views of the town). But I prefer this longer, even more dramatic route, via the fortified village of Monticchiello.
From the traffic circle at the entry to Pienza’s town center, instead of heading for Montepulciano, follow the road that runs along the left side of town (marked Amiata and Monticchiello—as you face Pienza, you’ll continue straight when the main road bends left). This road loops around behind and below the far end of the village, where you can consider a brief detour to see Pienza’s oldest church: Turn off on the right at the brown sign for Pieve di Corsigiano and drive a few hundred yards to Corsignano Parish Church (described on here).
Continuing on the main road past that turnoff, you’ll drop steeply down into the valley, feeling as if you’re sinking into a lavish painting. Dead ahead is Monte Amiata, the tallest mountain in Tuscany. This looming behemoth blocks bad weather, creating a mild microclimate that makes the Val d’Orcia a particularly pleasant place to farm...or to vacation. Meanwhile, don’t forget to savor the similarly stellar views of Pienza in your rearview mirror. After 5 kilometers, look on the left for the turnoff to Monticchiello (brown sign). From here, carry on for 4 kilometers—watching on the left for fine vistas of Pienza and for another classic twisty cypress-lined road—to the pleasant town of Monticchiello. This town, with an excellent recommended restaurant (Daria) and a compact, fortified townscape worth exploring, is a good place to stretch your legs; see more in the next section.
From Monticchiello, there are two routes back to Montepulciano: For the shorter route (6 kilometers), partly on gravel roads, drive all the way to the base of the Monticchiello old town, then turn right. For the longer route (10 kilometers), which stays on paved roads but circles back the way our loop started, turn off for Montepulciano at the main intersection, in the flat part of town that’s lower down.
Below are the main sights you’ll pass on my Heart of Tuscany driving route. Two of the main stops—the towns of Montepulciano and Pienza—are covered earlier in this chapter.
One of the finest gardens in Tuscany, La Foce (lah FOH-cheh) caps a hill with geometrical Italian gardens and rugged English gardens that flow seamlessly into the Tuscan countryside. The gardens were a labor of love for Iris Origo, an English-born, Italian-bred aristocrat who left her mark on this area and wrote evocatively about her time here. The gardens—which are worth a pilgrimage for garden lovers—can be visited only with a guided tour, and only three days a week (Wed, Sat, Sun) and some holidays.
Cost and Hours: €10; 45-minute tours offered April-Oct Wed at 15:00, 16:00, 17:00, and 18:00, Sat-Sun and holidays at 11:30, 15:00, and 16:30—but can be closed for private events, so check online in advance; private tours available, no tours in winter, ticket office opens 15 minutes before tour time, tel. 0578-69101, www.lafoce.com.
Getting There: La Foce sits in the hills above the busy town of Chianciano Terme. You can avoid SP-146 from Montepulciano through Chianciano (heavy traffic, poor signage) by following a more scenic route through the countryside (described at the start of my Heart of Tuscany Drive).
Eating and Sleeping near La Foce: Near the gardens, the Origo family runs a memorably charming roadside restaurant, $$ Dopolavoro La Foce (“After Work”). Once the quitting-time hangout for local farmers, today its interior is country-chic. The menu offers basic sandwiches or pasta and meat (featuring elegant hamburgers). The garden terrace out back is a chirpy delight, and the parking lot across the busy road offers one of the best vantage points on that perfect Tuscan road (Tue-Sun 9:00-22:00, closed Mon and Nov-March, Strada della Vittoria 90, tel. 0578-754-025, run with flair by Asia). Also nearby is their remote, restful B&B (described on here).
Thanks to the unique geology of this part of Tuscany (see sidebar, here), several natural hot springs bubble up between the wineries and hill towns. And the town of Bagno Vignoni (BAHN-yoh veen-YOH-nee)—with a quirky history, a pleasant-to-stroll street plan punctuated with steamy canals, and various places to take a dip—is the most accessible and enjoyable to explore. If you’d like to recuperate from your sightseeing and wine tasting by soaking in the thermal baths, bring your swimsuit.
Getting There: Bagno Vignoni is well signed, just off the main SR-2 highway linking Siena to Rome (5 kilometers south of San Quirico d’Orcia). Park in the pay lot (coins only) by the big roundabout and walk into town, taking the left fork (in front of Hotel Le Terme).
Bagno Vignoni Town Walk: Emerging into the main square, walk under the covered loggia and look out over the aptly named Piazza delle Sorgenti (“Square of the Sources”), filled with a vast pool. Natural spring water bubbles up at the far end at temperatures around 125 degrees Fahrenheit. Known since Roman times, these hot springs were harnessed for their medicinal properties in the Middle Ages.
You’re not allowed to wade or swim in this main pool today, but an easy stroll through town shows you other facets of these healing waters. Facing the pool, turn left, walk to the end of the loggia, then turn left again down Via delle Sorgenti. Listen for the water that gushes under your feet, as it leaves the pool and heads for its big plunge over the cliff. You’ll emerge at an open zone with the cliff-capping ruins of medieval mills and cisterns that once made full use of Bagno Vignoni’s main resource. Here you’ll have a chance to dip your toes or fingers into streams of now-tepid water. At the canals’ end, the water plunges down into the gorge carved by the Orcia River.
Taking the Waters: The modern Piscina Val di Sole bath complex, inside Hotel Posta Marcucci, is simple but sophisticated. It’s a serene spot to soak (in water ranging from 80 to 105 degrees Fahrenheit) while taking in soaring views of Rocca d’Orcia across the valley (€20-27, €5 towel rental with €10 deposit, Fri-Wed 9:30-18:00, Wed and Sat also 21:00-24:00, closed Thu, tel. 0577-887-112, www.postamarcucci.it).
Eating in Bagno Vignoni: The town’s class act is $$$ Osteria del Leone, on the cheery little piazzetta just behind the loggia, with charming tables out on the square. Inside it’s dull and modern, with a fine interior garden (closed Mon, Via dei Mulini 3, tel. 0577-887-300, www.osteriadelleone.it). For something a bit more affordable and casual, drop by the nearby $$ Il Loggiato, with stony indoor seating or outdoor tables (closed Thu, Via delle Sorgenti 36, tel. 0577-888-973).
The fortress looming over Rocca d’Orcia (ROH-kah DOR-chah) perches high above the main SR-2 highway. Likely inhabited and fortified since Etruscan times, this strategic hilltop was a seat of great regional power in the 12th century. During this time, Rocca d’Orcia was one of a chain of forts that watched over pilgrims walking the Via Francigena to Rome.
Today the Rocca di Tentennano fortress—an empty shell of a castle with modern steel stairs and a grand 360-degree panorama at its top—looks stark and abandoned. It seems to dare you to pay €3 to take the very steep hike up from the parking lots below (May-Sept daily 10:30-13:30 & 16:30-18:30; shorter hours off-season, mobile 392-003-3028 or 333-986-0788).
Eating in Rocca d’Orcia: On Rocca’s main square, $$ La Cisterna nel Borgo faces the town’s namesake cistern. Marta and Fede serve up deliciously executed dishes in a classic setting (Mon-Fri 12:00-14:00 & 19:00-22:00, Sat-Sun 19:00-22:00 only, Borgo Mestro 37, tel. 0577-887-280).
This 200-person fortified village clings to the high ground in the countryside just south of Pienza and Montepulciano. While not quite “undiscovered,” Monticchiello is relatively untrampled, and feels like a real place where you can get in touch with authentic Tuscan village life.
Eating in Monticchiello: At the warm and classy $$$ Ristorante Daria, owner Daria pleases diners with seasonal, traditional Tuscan dishes presented with flair in a modern setting. It’s in the heart of the stony hill town amid sumptuous scenery. Reservations are wise (Thu-Tue 12:15-14:30 & 19:15-22:00, closed Wed, Via San Luigi 3, tel. 0578-755-170, www.ristorantedaria.it). Arriving in Monticchiello, walk through the town’s gate, head about 50 yards straight up the hill, and bear right.