Top Choice Street in Montepulciano

Il Corso

Montepulciano's main street – called in stages Via di Gracciano, Via di Voltaia, Via dell'Opio and Via d'Poliziano – climbs up the eastern ridge of the town from Porta al Prato and loops to meet Via di Collazzi on t…
Top Choice Museum in Montepulciano

Museo Civico

Montepulciano’s modest museum and pinacoteca have recently had a curatorial dream come true: a painting in their collections has been attributed to Caravaggio. The masterpiece is a characteristic Portrait of a Gentl…
Top Choice Palace in Montepulciano

Palazzo Comunale

Built in the 14th-century in Gothic style and remodelled in the 15th century by Michelozzo, the Palazzo Comunale still functions as the town hall. The main reasons to head inside are to drink in the extraordinary vi…
Winery in Montepulciano

Fattoria Le Capezzine

This wine estate, 15km northeast of Montepulciano, is part of the legendary Avignonesi company, which produces Vino Nobile di Montepulciano, Rosso di Montepulciano, Vin Santo, grappa and olive oil. Spread over 19 he…
Cathedral in Montepulciano


Montepulciano's late-16th-century duomo is striking, largely because its unfinished facade gives the building an organic, heavily weathered look. Inside track down Taddeo di Bartolo's ornate Assumption triptych (140…
Church in Montepulciano

Chiesa di Sant'Agostino

Michelozzo's Chiesa di Sant'Agostino features a lunette above the entrance holding a terracotta Madonna and Child, John the Baptist and St Augustine.
Winery in Montepulciano

Cantina de’ Ricci

Piazza in Montepulciano

Piazza Grande

Elegant Piazza Grande is the town's highest point and if you think it looks familiar, it might be because it featured in New Moon, the second movie in the Twilight series based on Stephanie Meyer's vampire novels. T…
Street in Montepulciano

Via Ricci

From the central Piazza Grande, Via Ricci runs downhill past Palazzo Ricci, now home to a German music academy. The street terminates in Piazza San Francesco, where you can admire still more panoramic views of the …
Monument in Montepulciano

Colonna del Marzocca

At the upper end of Piazza Savonarola is the Colonna del Marzocca, erected in 1511 to confirm Montepulciano's allegiance to Florence. The splendid stone lion, squat as a pussycat atop this column is, in fact, a copy…