Montepulciano • Pienza and the Val d’Orcia • Montalcino and the Brunello Wine Country
Sights and Experiences in Montepulciano
Montalcino and the Brunello Wine Country
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 the region.
An hour south of Siena, this slice of splendor—which seems to specialize 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 sub-region of Tuscany is the best 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 down into the cliffs it sits upon, and a classic town square. Pienza is a sure-of-itself 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.
Don’t be overly focused on ticking off a list of sights here. This region’s attractions—while substantial—are best seen as an excuse for a countryside drive, and I’ve narrated a self-guided loop drive to help you connect the very best.
This region richly rewards whatever time you’re willing to give it. As this compact region is hemmed in by Italy’s two main north-south thoroughfares—the A-1 expressway and the scenic SR-2 highway—even those with a few hours to spare can get an enticing taste. But ideally, spend at least one night (or more if you enjoy wine and views). Many travelers enjoy home-basing here for a week, not only to see the many attractions listed in this chapter, but also to use this area as a springboard to visit Siena; even Volterra, San Gimignano, and Florence are all realistic as long side-trips.
Choosing a Home Base: Montepulciano is the most all-around engaging town, and works well for travelers with or without a car. With its easy access to the vineyards, Montalcino makes sense for wine pilgrims. For drivers who’d like to home-base in the scenic countryside, I’ve listed several agriturismi and other rural accommodations throughout this chapter, including a few that are strategically located near Pienza.
By Car: This area is ideal by car, and I’ve designed this chapter primarily with drivers in mind. The “Best of Tuscany” loop (here) links the two most charming large towns of the area (Montepulciano and Pienza) with the area’s best scenery, and its most offbeat and intriguing villages and countryside sights.
Driving in this area, navigate by town names, and equip yourself with a good map and/or mapping app on your mobile device: Many of the attractions I’ve described are on tiny back lanes, marked only with easy-to-miss, low-profile signs from the main roads. Even road names can differ between maps and local signage. Expect to backtrack periodically to find your turnoff. I’ve given distances in kilometers to match up with your rental car’s odometer.
Even many of the small towns in this area are designated as “limited traffic zones” marked ZTL or Zona Traffico Limitato, often with a red circle—off-limits to non-local traffic. While tiny village ZTLs aren’t monitored by cameras (as in big cities), you can still be ticketed if you’re found crossing that line. When parking, remember that white lines indicate free parking (sometimes time-limited—look for explanatory signs); 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 transportation (mostly 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. See the map on here for an overview.
A good local guide can help you take full advantage of everything this area has to offer. Roberto Bechi, based in Asciano near Siena, capably tells this region’s story (see listing on here). Antonella Piredda, who lives in the village of Montisi (just north of Pienza) 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, anto@antonellapiredda.com, www.antonellapiredda.com). Antonella also offers a beautiful apartment for rent in Montisi (www.casaparva.com).
Curving its way along a ridge, Montepulciano (mohn-teh-pull-chee-AH-noh) delights visitors with vino, views, and—perhaps more than any other 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, 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 good jumping-off point for my “Best of Tuscany” self-guided driving tour, described on here.
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 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 free town map, 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).
The office on the main square that looks like a TI 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, likely open Sat-Sun in summer, Piazza Grande 7, tel. 0578-717-484, www.stradavinonobile.it).
Well-signed pay-and-display parking lots ring the city center (marked with blue lines, usually €1.30/hour). But there are also a lot of free spaces mixed in (marked with white lines)—look around before you park.
If you want 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 un-numbered lot just above, directly in front of the stone gate. If these are full, try lots P2, P3 (with a 1-hour limit), or P4. Lot P5 is near the bus station (ride up to the gate on the elevator described below).
Alternatively, to get to the main square quickly, 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).
Avoid the “ZTL” no-traffic zone (marked with a red circle), and don’t park on yellow lines (which are for locals only). 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.
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.
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 (€2). Public WCs are located at the TI, to the left of Palazzo Comunale, and at the Sant’Agostino Church.
Laundry: An elegant 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: 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 348-702-4124 (www.strollingintuscany.com).
(See “Montepulciano” map, here.)
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 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.
(See “Montepulciano” map, here.)
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 “passaggio segreto” 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 segreto...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 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. 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, the 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 more similar to Greek than to the more recent 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 Church of Sant’Agostino. Huff 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 comedy theater (commedia dell’arte).
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 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, loaner 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—enjoy this nice, lazy, easy stretch. 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 see works by 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. Turn right and head uphill steeply; at #4 (on the left), marked Ramaio, is Cesare’s workshop and museum (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 later.
Either way, Montepulciano’s main square is just ahead. You made it!
(See “Montepulciano” map, here.)
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, behind the well (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, and the little white “pills” representing the family of “medics”).
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. You can pay to go just as far as the terrace, at the base of the tower (€2.50, 71 stairs), 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, where you enjoy commanding views of the region—all the way to Pienza (look just to the right of San Biagio Church; tower open daily 10:00-13:00 & 14:00-18:00, often 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 (Via Talosa). 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 de’ Ricci 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 the recommended Cantine de’ Ricci 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. If you’re visiting one of the wine cellars, read the sidebar on here.
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, and when it’s busy, 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. 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 9:30-12:30 & 14:30-19:00, 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. 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 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, closed Sun, Piazzetta del Teatro 4, 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, 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 two or three wines for free—or, if you show them this book, they’ll offer you the free wines along with some light food.
Cost and Hours: Free tasting, €7-8 bottles, affordable shipping, daily 10:30-19:00, next to Palazzo Ricci, look for signs either for Cantine de’ Ricci or Cantine del Redi—its former name, 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 the Elder 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: Likely €2, generally daily 8:30-18:30.
$$$ Mueblè il Riccio (“The Hedgehog”) is medieval-elegant, with 10 modern and spotless rooms, an awesome roof terrace, and friendly owners. Five are new “superior” rooms with grand views across the Tuscan valleys (Sb-€80, Db-€100, view Db-€110, superior Db-€150, superior Db with balcony-€180, Tb-€116, superior Tb-€180, superior Qb-€200, breakfast-€8, air-con, guest computer and Wi-Fi, limited free parking—request when you reserve, a block below the main square at Via Talosa 21, tel. 0578-757-713, www.ilriccio.net, info@ilriccio.net, Gió and Ivana speak English). Gió and his son Iacopo give tours of the countryside (€50/hour) in one of their classic Italian cars; for details, see their website. Ivana makes wonderful breakfast tarts.
$$$ La Locanda di San Francesco is pricey but luxurious, with four stylish rooms over a classy wine bar at the quiet top end of town (standard Db-€185, superior Db-€205, suite-€225, these are nonrefundable prices—pay €20 more for “flexible” rates, closed Nov-Easter, air-con, guest computer and Wi-Fi, free parking nearby, Piazza San Francesco 5, tel. 0578-758-725, www.locandasanfrancesco.it, info@locandasanfrancesco.it, Cinzia and Lucca).
$$ Albergo Duomo is big, modern, and nondescript, with 13 rooms (with small bathrooms) and a comfortable lounge downstairs. With a handy location just a few steps from the main square, it’s at the very top of town, with free parking nearby (Sb-€60, small Db-€80, standard Db-€100, Tb-€120, family deals, elevator, air-con in some rooms for €5 extra, Wi-Fi, loaner laptops, Via di San Donato 14, tel. 0578-757-473, www.albergoduomo.it, albergoduomo@libero.it, Elisa and Saverio).
$$ 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, 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, 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 countryside, consider the options listed under “Sleeping in the Val d’Orcia,” later. All are within a 5- to 15-minute drive of Montepulciano.
These places are all open for lunch (about 12:30-14:30) and again for dinner (about 19:30-22:00). I’ve noted closed days.
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, 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. Chiara serves while 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 €6-8 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 (€8-10 non-steak secondi, 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, €9-15 secondi, 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, closed Thu, Corso 86, tel. 0578-757-582).
Wine Bar: La Locanda di San Francesco, with a fine terrace at the tranquil top of town—in front of the namesake church and its spectacular view terrace—is a fine place to nurse a glass of local wine in elegant surroundings (€4-9 glasses; also €7-10 pastas, salads, and soups; €9 daily specials, no afternoon closure, closed Mon and Nov-Easter, Piazza San Francesco 5, tel. 0578-758-725).
Near Montepulciano, in Monticchiello: 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, where you can dine at the excellent La Porta restaurant, with its fine view terrace, or at the modern-feeling La Cantina (both described on here). To get to Monticchiello directly from Montepulciano, first take the road toward Pienza; then, 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 (partly gravel), middle-of-nowhere drive.
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 (1-2/day, 2 hours, change in Bettolle, LFI bus, www.lfi.it), Siena (6-8/day, none on Sun, 1.25 hours), Pienza (8/day, 30 minutes), Montalcino (3-4/day Mon-Sat, none Sun, change in Torrenieri, 1-1.25 hours total). There are hourly bus connections to Chiusi, a town on the main Florence-Rome rail line (50 minutes); 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 (3/day, none on Sun).
As the Montalcino connection is problematic by public transportation, consider asking at the TI for a taxi (also see contact numbers under “Helpful Hints” earlier). Although expensive (about €70), taking a taxi could make sense for two or more people. For drivers, it’s a straight shot on S-146 (through Pienza, great scenery, and several classic Tuscan views) to Montalcino; for a more scenic route see my “Best of Tuscany” loop drive (here).
The heart and soul of this part of Tuscany are the rolling farm fields near the valley of the Orcia River—called the Val d’Orcia (val DOR-chah). Tucked between Montepulciano to the east and the Montalcino hills to the west, the Val d’Orcia boasts some of the best scenery in Italy. The Renaissance town of Pienza is the area’s centerpiece, with the spa town of Bagno Vignoni, the hill-capping fortified towns of Monticchiello and Rocca d’Orcia, and countryside sights such as the elegant La Foce Gardens rounding out the Val d’Orcia’s appeal. As this is also one of Italy’s most rewarding areas to explore by car, consider following my “Best of Tuscany” self-guided driving tour.
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. 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.
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. Pienza is 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 (though for some excellent countryside options just outside of town, see here).
Nearly every shop sells the town’s specialty: pecorino, a pungent sheep’s cheese that sometimes contains other ingredients, such as truffles or cayenne 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 10:30-13:30 & 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: 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).
Buses drop you just a couple of blocks directly in front of the town’s main entrance.
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).
I’ve connected the town’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 half a day.
• 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. At the end of the second block on the left, at #21, step into the Marusco e Maria cheese-and-salami shop. Take a deep whiff and survey the racks of pecorino cheese, made from sheep’s milk. For €3 per person, Fabio can give you a quick taste of three types 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. 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. Step inside for a glimpse of the gloomy Middle Ages, which inspired Pius in all the wrong ways when it came time to build his church—he wanted the exact opposite of this atmosphere. Also peek into the adjacent, tranquil cloister.
• Continuing one more block, you’ll pop out at Pienza’s showcase square...
While Pienza’s main piazza is relatively small, and at first seems visually underwhelming, architecture highbrows consider it one of Italy’s most interesting squares for its elegance and artistic unity. The piazza and surrounding buildings were all designed by Rossellino 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 (described later). Notice that the grid lines in the square’s pavement continue all the way up the sides of this building, creating a Renaissance cube. 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 the town over the 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. Looking farther right, see the last building, the Bishop’s Palace (now housing the TI and the Diocesan Museum, described later), also called the Borgia Palace. Pius invited prominent cardinals to occupy the real estate in his custom-built town. 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. The Borgia were notorious for their shrewd manipulation of power politics. Our word “nepotism”—which comes from the Italian nipote (nephew)—dates from this era, when a pope would pull strings to ensure his relatives would succeed him. Finally, between the Bishop’s Palace and the Duomo, a lane leads to the best view terrace in town.
• Now take the time to tour whichever of the square’s attractions interest you (listed next).
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. Pius envisioned this church as an antidote of sorts to dark, claustrophobic medieval churches, like the one we saw earlier. Instead, this was to be a “house of glass,” representing the cultural enlightenment that came with the Renaissance. Instead of the colorful frescoes you’d expect, the church has clean, white walls to reflect the light. Windows feature the crescent-moons crest of Pius II, and Sienese Gothic altarpieces and painted arches round out the decor.
Cost and Hours: Free, generally daily 7:00-13:00 & 14:30-19:00.
The home of Pius II and the Piccolomini family (until 1962) can only be visited on an escorted audioguide tour (about 30 minutes total).
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. 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.
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—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.
After your brief orientation stroll, you can explore your choice of flower-lined back lanes. Work your way to the back-left corner of town, where—along Via delle Case Nuove—you’ll find 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: Buon Gusto is run by Nicola, who focuses on quality ingredients and intense flavors. He makes just a few batches each morning (typically ready by around 13:30—just in time for after lunch), and once they’re gone, they’re gone. He also does fresh pressed juices, smoothies, and jams designed to complement local cheeses and other flavors (Tue-Sun 11:00-20:00, until 22:00 in summer, closed Mon, Via delle Case Nuove 26, mobile 335-704-9165).
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), Montepulciano (8/day, 30 minutes), Montalcino (3-4/day Mon-Sat, none Sun, change in Torrenieri, 45-60 minutes total).
Route Tips for Drivers: My self-guided “Best of Tuscany” loop drive links Pienza to Montepulciano and sights in between.
In this section, I’ve listed the main sights in the Val d’Orcia from east to west. Then I’ve suggested a self-guided driving route to connect them (and other worthwhile stops).
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. A visit here comes with tales of an English-born, Italian-bred aristocrat—Iris Origo—who left her mark on this area, and wrote evocatively about her time here. The gardens can be visited only with a guided tour, and only three days each week (Wed, Sat, Sun). But a trip here comes with some grand scenery and is worth a pilgrimage for garden lovers.
Cost and Hours: €10; 50-minute tours offered mid-March-early Nov Wed at 15:00, 16:00, 17:00, and 18:00, Sat-Sun at 11:30, 15:00, and 16:30; no tours in winter, confirm tour time and reserve in advance, tel. 0578-69101, www.lafoce.com.
Getting There: La Foce sits in the hills above the busy town of Chianciano Terme. To avoid driving through Chianciano (heavy traffic, poor signage), consider a more scenic route through the countryside from Montalcino (described at the start of my “Best of Tuscany” driving tour on here).
Eating and Sleeping near La Foce: Near the gardens, the Origo family runs a memorably charming restaurant and a remote, restful B&B. The roadside restaurant Dopolavoro La Foce (“After Work”) was literally the after-work hangout for local farmers. Today its country-chic interior feels trendy, but with a respect for local tradition, and the garden terrace out back is a chirpy delight. (€4-5 panini-like bico sandwiches, €8-12 pastas, €10-13 secondi, Tue-Sun 8:00-23:00, closed Mon, Strada della Vittoria 90, tel. 0578-754-025).
$$$ The family’s B&B Palazzolo La Foce lets you sleep aristocratically in a small villa just below the gardens. Its four colorful rooms share a welcoming kitchen/lounge with a giant fireplace, and an outdoor swimming pool with glorious Tuscan views. Two rooms share a bathroom (D-€120, Db-€140, no air-con but breezy, Wi-Fi, Strada della Vittoria 61—but check in at gardens’ main entrance to get specific directions to your room, tel. 0578-69101, www.lafoce.com, info@lafoce.com).
This 200-person fortified village clings to the high ground in the countryside just south of Pienza and Montepulciano. As it’s not along a main road, it feels more remote (for route tips on getting there from Pienza, see here; from Montepulciano, see here). 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. It’s also a fine place for a meal.
Eating in Monticchiello: Just inside the town’s gate is La Porta, where warm and classy Daria pleases diners either indoors or out with traditional Tuscan dishes presented with flair (€9-14 pastas, €12-18 secondi; seatings at 12:30, 14:00, 19:30, and 21:30; closed Thu in Oct-March, Via del Piano 1, tel. 0578-755-163, www.osterialaporta.it). Or continue 50 yards up into town and turn right to find La Cantina, run by daughter Deborah (€9-10 pastas, €10-14 secondi, Tue-Thu 12:30-15:00 & 19:30-22:00, closed Wed, Via San Luigi 3, tel. 0578-755-280).
Thanks to the unique geology of this part of Tuscany, 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 (3 miles south of San Quirico d’Orcia). Park in the lot by the big roundabout (€1/hour) and walk into town, taking the left fork (in front of Hotel Le Terme).
Taking the Waters: The modern Piscina Val di Sole bath complex, inside Hotel Posta Marcucci, is simple but sophisticated—a serene spot to soak (€15, €5 towel rental with €10 deposit, April-Sept Fri-Wed 9:30-13:00 & 14:00-18:00, Oct-March Fri-Wed 10:00-17:00, closed Thu year-round, last entry one hour before closing, tel. 0577-887-112, www.piscinavaldisole.it).
Eating in Bagno Vignoni: Osteria del Leone, on the cheery little piazzetta just behind the loggia, is the town’s class act, with charming tables out on the square (€8-12 pastas, €10-18 secondi, 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 (€6-7 crostini and polenta dishes, closed Thu, Via delle Sorgenti 36, tel. 0577-888-973).
The looming fortress of Rocca d’Orcia (ROH-kah DOR-chah) perches high above the main SR-2 highway from Siena to Rome. Likely inhabited and fortified since Etruscan times, this strategic hilltop was a seat of great regional power in the 12th century, crowned by a fortress called Tentennano. Today the Rocca di Tentennano fortress feels abandoned, and is a very steep hike up from the parking lots that cling below its base (€3 entry; June-Sept daily 10:00-13:00 & 16:00-19:00; shorter hours off-season, mobile 333-986-0788, www.parcodellavaldorcia.com). The pleasant village of Rocca d’Orcia, just below the castle, is a sleepy and stony spot to stroll, but there’s not much to see.
Eating in Rocca d’Orcia: La Cisterna nel Borgo sits on Rocca’s main square, facing the town’s namesake cistern. Marta and Fede serve up deliciously executed dishes in a classic setting (€9-10 pastas, €11-13 secondi, cash only, closed Mon, Borgo Mestro 37, tel. 0577-887-280, www.cisternanelborgo.com).
If you have just one day to connect the ultimate Tuscan towns and views, this is the loop I’d stitch together. While the rockier wine country farther west and north has its fans, the appeal here is exactly the opposite: 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.
If you’re in a rush and don’t linger in any of the towns, you could do this drive (just for the views) in a couple of hours. To hit the sights, explore the towns, and linger over a meal or a glass of wine, you could split this up over several days. If you’re in the region for a longer stay, this is a great loop to do early in your visit, to get your bearings. I’ve started and ended the clockwise loop in Montepulciano, but you could just as easily start and end in Pienza (or anywhere else along the way). If gardens are your thing, try to do this loop when La Foce Gardens are open (Wed, Sat, or Sun), and time your drive to join one of their guided tours (see here). To make it easier to mix and match over several days, I’ve divided the directions into four legs.
Note that the first stretch of this loop includes some steep gravel roads, which help spare you a lot of traffic. But if that makes you uncomfortable, you could instead take the longer (and poorly signed) route farther south, via the congested, sprawling mess of Chianciano Terme.
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 and head toward Pienza—see here). Once you’re done there, drive south, at first following signs to Chianciano Terme and Chiusi. Just one kilometer south of Montepulciano, watch on the right for the turnoff to Castelluccio and Monticchiello. Zip along this scenic back road for five kilometers. You’ll pass the turnoff for Monticchiello on your right, but carry on straight ahead, as the road continues uphill and becomes gravel. Grinding your way up, you’ll enjoy views on the right of the jagged cliffs called calanchi and begin to get your first glimpse of the famous twisty road above La Foce Gardens. You’ll pass around the front door of an old country estate (just stick with the road as it curves), and pop out at the T-intersection in front of the entrance to the recommended La Foce Gardens (from this intersection, parking and reception is just to the left—look for Loc. La Foce; for details, see here). To skip the gardens and continue with the loop, turn right at this T-intersection, toward Siena/Roma/Cassia.
From La Foce, head downhill 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 (the restaurant itself is 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 five 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 and the Brunello region (near Montalcino) to the west are 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) for Pienza, which you’re welcome to take if you’re in a hurry to cut the loop short (just 8 scenic kilometers). But there’s so much more to see; I’d rather carry on.
The tower looming on the hill ahead of you is Rocca d’Orcia (which you can visit as an optional detour—see 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 essentially the same purpose, as an agriturismo called La Grancia (“The Granary”).
When you reach the T-intersection with the main S-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 dating back centuries—see here. (To see the empty fortress at Rocca d’Orcia—and its views—you can overshoot Bagno Vignoni by just 1 kilometer and turn to here.)
When you’re ready to move on, head north on SR-2 (toward San Quirico d’Orcia and Siena). After just four kilometers, in San Quirico d’Orcia, turn off onto the SP-146 road to Pienza, also marked for Chiusi, Chianciano Terme, and Montepulciano. (Or, if you’re collecting views and don’t mind backtracking a bit, carry on past San Quirico straight—toward Siena—for four kilometers and pull over next to the circle of cypress trees in a field called the Rondò. After seeing it, return to San Quirico, then head toward Pienza.) Along the San Quirico-Pienza road—one of the region’s most scenic—you’ll enjoy grand views 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 on here.
If you’re in a hurry or losing sunlight, just hop back on the main SP-146 road—it’s a 12-kilometer straight-shot back to Montepulciano (enjoying some pullouts with fine views of the town on the left). But I prefer this longer, even more scenic 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 just a few hundred yards to the Romanesque Corsignano Parish Church, a reminder of a much earlier, rougher, simpler time (before Pope Pius II). The facade is carved with unusual iconography from an age when the pagan roots of early Christianity were vivid and unmistakable. The gloomy, cave-like, somber interior—with three parallel naves—is a far cry from later, brighter styles. Near the entrance on the right is the font that was used to baptize the man who would grow up to be Pope Pius II.
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. Your view is dominated by 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 five kilometers, watch on the left for the turnoff to Monticchiello (brown sign). From here, carry on for four kilometers—watching on the left for fine views of Pienza, and for another classic “twisty cypress-lined road” view —to the pleasant town of Monticchiello. This town, with an excellent recommended restaurant (La Porta) and a compact, fortified townscape with exploring, is a good place to stretch your legs (and described on here).
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 loops back the way our loop started, turn off for Montepulciano at the main intersection, in the flat part of town that’s lower down.
While I wouldn’t hang my hat in sleepy Pienza itself, some fine countryside options sit just outside town. The first two are immersed in Tuscan splendor, midway between Montepulciano and Montalcino (on the main road from Pienza toward Montalcino, about 2.5 miles outside of Pienza); the third, La Bruciata, is on the other side of Pienza, in the direction of Montepulciano.
$$$ Agriturismo Cretaiole, ideally situated in pristine farmland just outside Pienza, is perfect for those who want to settle in for a week and fully experience Tuscany. This family-friendly farm welcomes visitors for weeklong stays (generally Sat-Sat) in six comfortable apartments. One of my favorite agriturismo experiences in Italy, Cretaiole is warmly run by reformed city-slicker Isabella, who came here on vacation and fell in love with country-boy Carlo. Now Carlo and his father, Luciano, tend to the farm, while Isabella and her helper Carlotta pride themselves on personally assisting guests in finding exactly the Tuscan experience they’re dreaming of. More than just a place to stay, Cretaiole is a remarkably rich cultural education; Isabella has thoughtfully planned an extensive slate of optional activities (each one for a reasonable extra charge). These can include pasta-making and olive-oil tasting classes, family-style Tuscan dinners, winery tours, truffle hunts and grape and olive harvesting (in season), artisan studio visits, Siena side-trips, watercolor classes, and more. All of these activities make Cretaiole feel like an idyllic summer camp for grown-ups. While you could just let momentum overtake you here—not a bad plan, given the grand views from the manicured lawn—those wanting to delve more deeply into Tuscany should opt for the fairly priced “Dolce Vita Stay” package (Db-€860/week, small Db apartment-€1,050/week, large Db apartment-€1,350/week, same apartment for a family of up to four-€1,550/week, larger apartments available, these prices promised with this book in 2015; weeklong stays preferred but shorter stays possible when it’s slow—Db-€130/night, 3-night minimum, you can only book one month ahead; fewer activities and lower prices mid-Nov-mid-March, no air-con or swimming pool—for philosophical reasons, Wi-Fi, loaner bikes, loaner mobile phones, Isabella’s mobile 338-740-9245, Carlotta’s mobile 338-835-1614, tel. 0578-748-083, www.cretaiole.it, info@cretaiole.it). The same family runs two properties in the atmospheric medieval village of Castelmuzio, five miles north of Pienza (both with access to activities at the main agriturismo): Le Casine di Castello is a townhouse with two units (same prices as Cretaiole), while the more upscale Casa Moricciani is a swanky villa with dreamy views, plush interiors, and loads of extras (€3,250/week upstairs, €4,250/week downstairs, each has 2 bedrooms and 2 bathrooms; www.buongiornotoscana.com).
$$$ Fonte Bertusi, a classy and artistic guesthouse (not an agriturismo) nearly across the road from Cretaiole, is well-run by young couple Manuela and Andrea, Andrea’s father Edoardo, and their attention-starved cats. They have a cozy library/lounge/art gallery that hosts installations and occasional music events, and they’ve scattered vivid, whimsical bits and pieces of artwork around the complex. The eight apartments mix rustic decor with avant-garde creations; it’s a bit pricey, but the setting is sublime (nightly rate: 1-bedroom apartment-€130, 2-bedroom apartment-€260, includes breakfast; weekly rate: €750-1,150, €50 extra per person for breakfast all week; Wi-Fi, laundry service, swimming pool, grand view terrace, 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, Manuela’s mobile 339-655-5648, www.fontebertusi.it, info@fontebertusi.it).
$$$ La Bruciata is a family-friendly agriturismo charmingly tucked in remote-feeling countryside just a five-minute drive outside of Montepulciano (on the way to Pienza). Can-do Laura and her family produce wine and olive oil, and rent seven tasteful, modern rooms split among four apartments (for 2-6 people each). In the summer (June-Aug), they prefer one-week stays, but shorter visits are possible at other times (Db-€100-120 depending on size, air-con for extra charge, Wi-Fi, farm-fresh meals and cooking classes for extra charge, 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 red La Bruciata signs (using gravel roads).
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 and a smattering of classy shopping, 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 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 Montalcini 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).
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. Those with a sweet tooth will enjoy crunching the Ossi di Morto (“bones of the dead”) cookies popular in Tuscany.
Montalcino also provides a handy springboard for exploring the surrounding wine region—with a more varied landscape than the Val d’Orcia near Montepulciano and Pienza. “Montalcino” literally means “Mountain of Holm Oaks”—and sure enough, its surrounding hills are generously forested.
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/person service fee); and have 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: 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 Soccorso church and a long pay lot with the same prices. Otherwise, park for free a short walk away.
The bus station is on Piazza Cavour, about 300 yards from the town center. From here, simply follow Via Mazzini straight up into town. While Montalcino has no official baggage storage, a few shops are willing to hold onto one or two bags on a short-term basis; ask at the TI for details.
Helpful Hints: Market day is Friday (7:00-13:00) on Viale della Libertà (near the Fortezza).
This 14th-century fort, built under Sienese rule, is now little more than an empty shell. 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 climb the ramparts for a panoramic view, you’ll have to pay. Most people visit the fortress for its wine bar (see here).
Cost and Hours: €4 for rampart walk—buy ticket and enter in the wine bar, €6 combo-ticket includes Montalcino Museums (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, daily 10:00-13:00 & 14:00-17:50, 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 in 2015 when you book directly with the hotel and mention this book, extra bed-€40, air-con, elevator, 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).
$$ Palazzina Cesira, right in the heart of the old town, is a gem renting five spacious and tastefully decorated rooms in a fine 13th-century residence with a palatial lounge and a pleasant garden. You’ll enjoy a refined and tranquil ambience, a nice breakfast (with eggs), and the chance to get to know Lucilla and her American husband Roberto, who are generous with local advice (Db-€105, suites-€125, cash only, 2-night minimum, 3-night minimum on holiday weekends, air-con, guest computer and Wi-Fi, free off-street parking, Via Soccorso Saloni 2, tel. 0577-846-055, www.montalcinoitaly.com, p.cesira@tin.it).
$$ B&B da Idolina has four good, midrange rooms above a wine shop on the main street (Db-€75, includes basic breakfast in shared kitchen, Wi-Fi, check-in available 14:00-20:00—call if arriving later, Via Mazzini 65, mobile 333-771-2102, www.poggiorubino.it, camereidolina@poggiorubino.it, Alessandro).
$ Affittacamere Mariuccia has three small, colorful, good-value, Ikea-chic rooms on the main drag over a heaven-scented bakery (Sb-€40, Db-€60, air-con, Wi-Fi, 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 347-365-5364, 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, free Wi-Fi, Piazza Cavour 4, tel. 0577-848-257, mobile 338-684-3163, albergoilgiardino@virgilio.it; Roberto and dad Mario).
$$ 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 (Db-€95, or €65 in Oct-mid-May; Qb-€130, or €95 in Oct-mid-May; lower weekly rates, reception open 10:00-12:00 & 15:00-18:00, metered gas heating, laundry service-€8/load, covered pool, hot tub, fitness room, La Croce 15, tel. 0577-847-133, www.lacrociona.com, info@lacrociona.com). The farm is 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 directions to Tenuta Crocedimezzo e Crociona. For location, see the map on here. 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 (€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, Sat-Thu 12:00-15:00 & 19:00-22:00, closed Fri, 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 (€5-6 pizzas, €8 pastas, €8-13 secondi, daily 12:00-15:30 & 19:00-23:00, Via Soccorso Saloni 10, 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,” below, 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; I’ve listed fine wineries on here, and a recommended driving loop on here. But if you’re short on time (or don’t have a designated driver—penalties here are harsh for driving under the influence), 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.
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 (€6-13 Brunellos by the glass, €3-5 light snacks, €8-12 plates; same prices inside, outside, or in back room; daily 7:30-23:00, 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.
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 most other enoteche in town, 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).
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, 1.25 hours). To reach Pienza or Montepulciano, ride the bus to Torrenieri (3-4/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 to Pienza; 45 minutes to Montepulciano). A local bus runs to Sant’Antimo (3/day Mon-Fri, 2/day Sat, none on Sun, 15 minutes, 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.
Route Tips for Drivers: The town is a short trip from my loop drive of the “Best of Tuscany” area (here).
The Montalcino 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/person service fee). Or check with the vintners’ consortium (tel. 0577-848-246, www.consorziobrunellodimontalcino.it, info@consorziobrunellodimontalcino.it).
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).
The local wine-tasting culture is nothing like the Napa Valley scene—you typically can’t just show up and expect to taste a few sips. If you’re serious about tasting, make a reservation in advance for a tour and guided tasting (an in-depth visit that usually lasts about an hour). I’ve highlighted a few places that are a bit more flexible, but even at these, there’s a fairly narrow window during which drop-ins are welcome, so keep a close eye on those hours.
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. Italian vintners understand that North Americans can’t take much wine with them, and they don’t expect to make a big sale, but they do hope you’ll look for their wines in the US. Some shops and wineries can arrange shipping.
This endearingly small, friendly, family-run winery, about a five-minute drive south of Montalcino, is operated by gregarious Gigliola and her assistant, Michele. The name is a type of small bird that also means “Little Girls,” in honor of Gigliola’s daughters. It’s best to call or email ahead to schedule a one-hour tour and tasting (€15, includes 3 tastes). But on most afternoons (Tue-Sun) you can drop by between 12:00 and 15:30 for a quicker, more casual taste without the full tour (€10-36 bottles, Loc. Le Prata 262, tel. 0577-846-168, www.lepotazzine.it, tenuta@lepotazzine.it). Leaving Montalcino, follow signs up to Grosseto and S. Angelo. Watch for the turnoff on the right for Camigliano and Tavernelle (onto SP-103), then carefully track Le Potazzine signs through the countryside (bear right at the fork, then watch for their driveway on the left).
Perched high above the Sant’Antimo Abbey, this winery hits a nice balance: Run by three brothers from Rome, it’s owned by the big Illy coffee company. This big, glitzy winery overlooks vast vineyards and spectacular views, yet doesn’t feel as corporate or soulless as some of the bigger players. You can call ahead to arrange a full tour and tasting (€10). Or, for a more casual experience, stop by any weekday afternoon (Mon-Fri 13:00-15:00) for a tasting and a brief tour (€17-36 bottles, 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 along the gravel road up, up, up (enjoying vineyard and abbey views) to the end.
Easier to remember by just its first name (think Chachi from Happy Days), this offers a great combination of a well-respected, family-run vineyard that’s big enough to offer a drop-in-anytime tasting room. Situated down a back lane on the way from Sant’Antimo Abbey to the “La Sesta” gravel road, Ciacci has a classy tasting room/enoteca and an outdoor view terrace. Belly up to the wine bar for two or three free tastes, or order a more formal tasting of top-quality wines for €10-25, which includes a tour of the cellar (reserve ahead for full tasting; for a casual taste just drop by Mon-Fri 9:00-19:00, Sat-Sun 10:30-18:30, tel. 0577-835-616, www.ciaccipiccolomini.com, info@ciaccipiccolomini.com).
Elegant and aloof, 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. While you can try just dropping in, to be assured of a tasting it’s better to call ahead (€12.50-35 tastings, generally daily 8:30-13:00 & 14:30-17:00, Loc. Altesino 54, tel. 0577-806-208, www.altesino.it, info@altesino.it). Leaving Montalcino toward Buonconvento, watch for Altesino signs on the right. Head up this gravel road and behind the big building, following brown-and-yellow Altesino signs to their dramatic cypress-lined driveway.
On the outskirts of Torrenieri, this may be the quintessential family-run winery, with an emphasis on quality over quantity. For that reason, you’ll have to reserve ahead for a tasting here, but it’s worth the hassle. Flatter, a bit less scenic, and much more rustic (with a working-farm feel rather than a swanky tasting room) than the others listed here, this is a Back Door experience. They also produce excellent olive oil and top-notch prosciutto and salami (€15 for tasting and tour, €12-27 bottles, Loc. San Giulia 48, tel. 0577-834-270, www.santagiuliamontalcino.it, info@antagiuliamontalcino.it). It’s tricky to find: 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. Chiara; you’ll take gravel roads through farm fields to the winery.