Take the Bus -- Montepulciano's Corso is very steep indeed. For those not up to the climb, little orange pollicini buses connect the junction just below the Porta al Prato and Piazza Grande in about 8 minutes. The official point of origin is “the fifth tree on the right above the junction.” Tickets cost 1€ each way (buy them on the bus) and run every 20 minutes.

Outside the city walls below Porta al Prato squats the church of Sant' Agnese, with a striped 1935 facade surrounding a 14th-century portal. Inside, the first chapel on the right (hit the free light switch) has a frescoed Madonna by Simone Martini. Ring at the door to the right of the altar for access to the pretty cloister. Die-hards can make the 1.6km (1-mile) trek down Viale Calamandrei to Santa Maria delle Grazie, with Mary of the Graces and Annunciation figures by Giovanni della Robbia on the second altar and a rare late-16th-century organ with cypress wood pipes to which musicians from all over the world travel to play.

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You'll see architecture by Antonio Sangallo the Elder before you even get inside the walls. Porta al Prato was reconstructed in the 1500s on his designs, and the Medici balls above the gate hint at Montepulciano's long association with Florence. One block up Via Gracciano nel Corso, a Florentine Marzocco lion reigns from atop a column. (It's a copy of a 1511 original, now in the town museum.) To the right (no. 91) is the massive Palazzo Avignonesi, with grinning lions' heads, and across the street is the Palazzo Tarugi (no. 82). Both are by Vignola, the late Renaissance architect who designed Rome's Villa Giulia. A bit higher up on the left is the Palazzo Cocconi (no. 70) by Sangallo; the top floor looks out of place because it was added in the 1890s. In lieu of an Etruscan museum, Montepulciano has the Palazzo Bucelli (no. 73), the sort of place that makes archaeologists grimace -- the lower level of the facade is embedded with a patchwork of Etruscan reliefs and funerary urns. Most probably came from the Chiusi area, and they represent the collection of 18th-century antiquarian scholar and former resident Pietro Bucelli.

Next on the right is Sant'Agostino, with a facade by Michelozzo in a style mixing late Gothic with early Renaissance. The first altar on the right has a Resurrection of Lazarus by Alessandro Allori. Over the high altar is a wooden crucifix by Donatello, and, behind it, the entrance to the choir of an older church on this spot, with frescoes and an Antonio del Pollaiolo crucifix. On the right as you leave is a painted Crucifixion by Leonardo da Vinci's protégé Lorenzo di Credi. On Piazza Michelozzo in front of the church stands the Torre di Pulcinella, a short clock tower capped with a life-size Pulcinella, the black-and-white clown from Naples, who strikes the hours. It was left by a philandering Neapolitan bishop who was exiled here for his dalliances. At the next corner on the left is the Palazzo Burati-Bellarmino (no. 28), where the door is kept open so you can admire the Federico Zuccari frescoes on the ceiling inside.

The road now rises steeply to Piazza delle Erbe and the Logge del Grano, a palazzo designed in the 15th century by Vignola with an arcaded porch and the Medici balls prominent above the entrance. The main road (it takes a left here) now becomes Via di Voltaia nel Corso, passing Il Capriccio, at no. 14 (tel. 0578-717-006), the town's best gelato vendor, then the grandiose Palazzo Cervini (no. 21) on the left, probably designed by Antonio Sangallo the Younger (Sangallo the Elder's nephew) for Cardinal Marcello Cervini just before he was elevated to the papacy. One of the shortest-lived pontiffs, Pope Marcellus II died 21 days into office. Climbing farther, you'll pass the 19th-century Caffè Poliziano, which serves snacks and pastries in elegant, Liberty surrounds. Next comes the rough facade of the baroque Chiesa del Gesù (the little trompe l'oeil cupola on the dome inside is courtesy of Andrea Pozzo) and, much farther on -- the street's name is now Via del Poliziano -- the house where Poliziano was born stands at no. 5. A scholar, writer, and philosopher, Angelo Ambrogini (called Poliziano after the Latin name of his hometown) had an enormous impact on the Florentine humanist movement as a friend of Lorenzo de' Medici and tutor to his children. Just before his house, Via delle Farine leads left to Porta delle Farine, an excellent and intact example of a 13th-century Sienese double gate.

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The main road now passes out of the city walls, wrapping around the Medici fortress (now private) and passing the seldom-open Santa Maria dei Servi, with another late-17th-century interior by Andrea Pozzo and a Madonna and Child by the Duccio school (inserted into another panel in the third altar on the left).

Back inside the walls, you come to Montepulciano's historic and civic heart, Piazza Grande. On the left is the Palazzo Comunale, designed by Michelozzo as a late-14th-century homage in travertine to Florence's Palazzo Vecchio. (Teens may recognize it from the 2009 vampire movie Twilight: New Moon -- filmed here, despite being set in Volterra.) Daily from 10am to 6pm, you can wander through civic offices to climb the tower for a great view of the surrounding countryside. (It's 2€ to climb, free for children 12 and under; watch your head.) Back on terra firma, to your left is the Palazzo Nobili-Tarugi, with an arcaded loggia on the corner facing a well topped by the Medici arms flanked by two Florentine lions and two Poliziani griffins. Both the palace and well are the design of Antonio Sangallo the Elder, as is the Palazzo Contucci across from the Palazzo Comunale.

The last side of Piazza Grande is taken up by the rambling brick nonfacade of the 17th-century Cattedrale di Santa Maria Assunta, a somewhat embarrassing reminder to Poliziani that, after building so many palaces and fitting so many of them with travertine, the city ran out of money to finish the ambitious plans for rebuilding the cathedral and had to leave it faceless. To the left of the church, the suspiciously 1950s-looking bell tower is actually the oldest thing on the piazza, dating from the 14th century and the cathedral of Santa Maria that once stood here. Inside, the Duomo makes up for its plain facade with two important works. The first takes some explaining because it's scattered in pieces around the church. Between 1427 and 1436, Michelozzo carved a monumental tomb for Bartolomeo Aragazzi, secretary to Pope Martin V. In the 18th century it was disassembled and the pieces lost until they were discovered under the altar of the Duomo in 1815. Two of the figures were stolen and found their way to London, but the rest remain here. Because no indication of what the monument originally looked like exists and the supporting architecture is gone, the various figures are distributed throughout the church. They start with a reclining statue of the deceased to the right of the central entrance door (he's the one with the hood) and two bas-reliefs on the first two columns on either side of the nave. The Greco-Roman-influenced statues flanking the high altar and the putti frieze above it, along with a statue in a niche to the right of the altar, are the other main pieces.

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The gold-heavy triptych on the high altar is by Taddeo di Bartolo (1401) and depicts the Assumption of the Virgin with Saints topped by Annunciation and Crowning of the Virgin pinnacles, and is banded with a Passion cycle in the predella. Bartolo was one of the Sienese artists of the generation after the 1348 Black Death, and this is one of his greatest works. (We particularly enjoy the predella panel where one child is shinning up a tree to get a better view of Christ entering Jerusalem.) On a pilaster to the right of the altar is a schiacciato bas-relief tabernacle by Vecchietta. Also inside the Duomo, as you walk out on the right, is an almond-eyed Madonna and Child (1418) by Sano di Pietro, located on the pilaster between the first two chapels. In the last chapel stands a 14th-century baptismal font with bas-relief and caryatid figures and, on the wall, della Robbia's Gigli Altar surrounding a gilded marble bas-relief of the Madonna and Child by Benedetto di Maiano.

A short walk north along Via Ricci brings you to Piazza San Francesco, where views extend south across the Valdichiana to Lago Trasimeno in Umbria and northeast across the hilly Val d’Orcia toward Siena.

Down the hill opposite the Duomo is Montepulciano's modest Museo Civico Pinacoteca Crociani, Via Ricci 10 (tel. 0578-717-300), whose star attractions are two blockbuster painted terra-cotta altars by Andrea della Robbia. Admission costs 5€, or 3€ for children 18 and under and those 65 and over. Opening hours are complex, but you should find it open Tuesday through Sunday most weeks outside quiet winter months, when it may be open on Fridays and weekends only.

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Continue down Via Ricci to the intersection with Via del Paolino, where you can cut back to the left on Via de' Grassi. Outside the walls is Antonio da Sangallo the Elder's Tempio di San Biagio (1518-34), one of the undisputed masterpieces of High Renaissance architecture. It became fashionable in the High Renaissance to build a church, usually on a Greek cross plan, just outside a city so that the classically inspired architecture would be unimpaired by surrounding buildings and the church could be appreciated from all angles. Todi and Prato each have their own version, but Montepulciano's is the best of the lot, a pagan temple built entirely of travertine, dedicated to the gods of mathematical and architectural purity and only nominally to any saint. Two bell towers were to have been fitted into the corners at the front, but the right one reached only 4.5m (15 ft.). The interior, while as peaceful and elegantly restrained as the overall structure, has nothing to hold you. Sangallo also designed the companion canon's house nearby, which was built after his death.

Underground Tunnels & Noble Wine

The local wine consortium, the Consorzio del Vino Nobile di Montepulciano (www.consorziovinonobile.it), has a showroom and tasting center in the basement of the Palazzo del Capitano on Piazza Grande where you can sample the wares of every member (which means most Vino Nobile vineyards) Easter–Oct Mon–Fri 11:30am–1:30pm and 2–6pm, Sat 2–6pm. If you’re heading into the country for some wine touring, staff here can provide maps. Across the corridor, the Strada del Vino Nobile office (www.stradavinonobile.it; tel. 0578/717484) can help you arrange a wine itinerary.

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Montepulciano has more enoteche and cantine (wine cellars) than you can shake a wine bottle at, most offering the chance to sample local products: pecorino cheese, salami, honey, olive oil, and, of course, Vino Nobile di Montepulciano. Many shops also let you descend into their cantine, often a linked maze of basements, underground tunnels that once connected the palaces, and older grottoes carved into the tufa of the mountain. Calling the grottoes "Etruscan tombs," as the signs in the stores proclaim, may not be far from the truth -- the earliest foundations of a city on this site are still contested.

The cantine with the most attention-grabbing tunnels include Ercolani, Via Gracciano nel Corso 82 (tel. 0578-716-764), which boasts a città sotteranea (or "underground city") in its lengthy cellars, featuring a "medieval torture room," an Etruscan tomb, and a collection of iron implements found here -- medieval weapons, household tools, and even a chastity belt. The Gattavecchi cantine, Via di Collazzi 74 (tel. 0578-757-110; www.gattavecchi.it), burrow under Santa Maria dei Servi, with moldy tunnels and a staircase leading down to an even moldier chapel-like structure carved out of the rock -- no one knows when it dates from or what it was, but it's intriguingly and suggestively located directly below the altar end of the church. Gattavecchi’s Vino Nobile is topnotch, as is the 100% Sangiovese Parceto. Tasting is free. Cavernous cellars at Cantina Ricci, Via di Collazzi 7 (www.cantinadericci.it; tel. 0578/757166), seem to spread beneath half of Montepulicano, with the main cellar, soaring 60 feet high, filled with centuries-old oak barrels. The cantina is open daily, with tastings (glasses from 2€, at the end of the tour. Contucci (www.contucci.it; tel. 0578/757006), in the 11th-century cellars of a historic palace in Piazza Grande, has a fine range of Vino Nobile wines; it’s open for free tastings every day of the year. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.