This hilltop medieval town in Tuscany has winding streets, Renaissance palaces, and terraced squares. Home to the prestigious Vino Nobile red wines and authentic local hospitality.
Montepulciano sits 605 meters above sea level in southern Tuscany. Its medieval streets lead to Piazza Grande, where you can climb the Palazzo Comunale's tower for views across two valleys. Below the streets, limestone tunnels house thousands of oak barrels aging Vino Nobile wine. The Renaissance-era Palazzo Tarugi displays its travertine facade along Il Corso, while the white dome of San Biagio church rises among cypress trees at the base of the hill.
Walking Through Montepulciano
Il Corso stretches 1.5 kilometers uphill from Porta al Prato to Piazza Grande. Though it changes names several times, you'll walk past uniform stone buildings with green shutters throughout. Wine shops stock bottles from local vineyards, while delicatessens sell pecorino cheese and pork products. The street's 7-degree incline becomes particularly challenging in the final 200 meters before Piazza Grande.
Piazza Grande and Its Buildings
At Montepulciano's highest point, medieval and Renaissance buildings frame the main square. The 14th-century Palazzo Comunale's red-brick tower rises 40 meters high - climb its 120 steps for panoramic views over Val d'Orcia and Val di Chiana. The Cathedral's rough stone facade remains incomplete since the 16th century. In the square's center, a well displays carved griffins and lions from 1520.
Underground Wine Cellars
Networks of tunnels run beneath the town center, maintaining temperatures of 13-15°C year-round. At Cantina Contucci, you can walk through vaulted chambers dating from the 13th century, where oak barrels age Vino Nobile for two years. Cantina De'Ricci's tunnels extend three levels deep, with guided tours explaining the wine-making process as you explore the medieval cellars.
The Bravio delle Botti Festival
On August's last Sunday, teams from eight districts compete in rolling 80-kilogram wine barrels up Il Corso. The race evolved from a horse competition in 1373 to its current form in 1974. Two pushers per team navigate their barrel through narrow streets and sharp corners. The 1.5-kilometer course ends in Piazza Grande, where the winning district receives a hand-painted banner.
Madonna di San Biagio Church
A 700-meter cypress-lined road leads from the town walls to this Renaissance church. Architect Antonio da Sangallo the Elder designed its Greek cross plan in 1518, completing construction in 1545. The church has one finished bell tower and one that remains half-built. Its white travertine walls stand out against the green valley, making it a landmark visible from 10 kilometers away.
Getting Around Montepulciano
Park at one of five lots outside the town walls - the largest, P1, sits near Porta al Prato with 200 spaces. The ZTL (Limited Traffic Zone) restricts car access in the center from 10:00 to 20:00. A mini-bus runs every 30 minutes between the lower and upper town, stopping at major squares. When walking, wear rubber-soled shoes for grip on the polished stone streets.
Day Trips from Montepulciano
From Montepulciano, you can reach several Tuscan towns within an hour. Pienza lies 13 kilometers west, where you'll find Renaissance palaces and shops selling aged pecorino cheese. Drive 40 minutes to reach Montalcino's medieval fortress and Brunello wineries. The thermal pool at Bagno Vignoni, unchanged since Roman times, sits 30 minutes southwest by car.
