With medieval monuments, traditional taverns and wine bars set around labyrinthine streets, Montepulciano is everything you would expect of a Tuscan hill town. Montepulciano’s beguiling architectural landscape bears testament to the affluence of the aristocratic families that resided here between the 14th and 16th centuries. This is offset by a stunning setting above the Val di Chiana and Val d’Orcia, two valleys decorated with olive groves, patchwork fields and sprawling vineyards.
The town’s atmospheric heart is an area of narrow and hilly lanes set inside ancient walls. Enter through Porta al Prato and make your way along Il Corso, the town’s main thoroughfare. See Gothic and Renaissance palaces located beside bars, boutiques, cafés and fashion outlets. Pause to admire centuries-old treasures such as Palazzo Avignonesi, Chiesa di Sant’Agostino and Torre di Pulcinella.
Veer off Il Corso to visit Piazza Grande, the town’s sumptuous central square and its highest point. Gaze at the unfinished façade of the 16th-century Montepulciano Cathedral, which houses works by Sienese masters. Enjoy panoramic views of lush countryside from the tower of the town hall, Palazzo Comunale. On clear days you can see the towns of Montalcino and Pienza in the near distance.
Continue to the Fortezza and look down on the beautiful Renaissance church, Chiesa di San Biagio. Spot art and Etruscan civilization artifacts at the Museo Civico.
Take a break from sightseeing at the osteria (taverns) and traditional trattorias. The town is famous for its production of the Nobile di Montepulciano and Rosso di Montepulciano red wines. These are readily available at the enoteche (wine bars) and wine-tasting cellars on Il Corso. Learn more about the town’s viticulture on a tour of Fattoria le Capezzine, a vineyard just a 20-minute drive west.
Montepulciano sits toward the southeast corner of the province of Siena. Daytrip buses travel regularly throughout the year from Florence and Siena. Rent a car and take advantage of the town’s convenient location close to other Tuscan hill towns, including Monticchiello and San Quirico d’Orcia.