Walking Tours

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.

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 Gracchino nel Corso, a Florentine Marzocco lion reigns from atop a column. (It's a copy of a 1511 original, now in the 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 grit their teeth -- the lower level of the facade is embedded with a patchwork of dozens 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 del Voltaia nel Corso, passing 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 elegant 19th-century Caffè Poliziano, which serves snacks and pastries. 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.

The main road now passes out of the city walls, wrapping around the Medici fortress (now a school) 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 (third altar on 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 variation in travertine on Florence's Palazzo Vecchio. Monday through Saturday from 8am to 1pm, you can wander through dingy civic offices and past overflowing file cabinets to climb the tower for a great view of the surrounding countryside. (It's free; watch your head.) Back on terra firma, to your left is the Palazzo 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 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 Duomo, 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 eventually 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 of the monument.

The gold-heavy triptych on the high altar is by Taddeo di Bartoldo (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. Bartoldo was one of the masters of late-14th-century Sienese art, and this is one of his greatest works. (I particularly like the predella panel where one child is shimmying 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, a della Robbia altar surrounding a gilded marble bas-relief of the Madonna and Child by Benedetto di Maiano.

Continue down Via Ricci to the intersection with Via del Paolino, where you can cut back to the left on Via de' Grassi. Head outside the city walls and you'll be on the road toward Antonio da Sangallo the Elder's Tempio di San Biagio (1518-34), one of the true 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 and uninhibited 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.