Between Wine, History and Festivals
Perched on a limestone hill between the Val d’Orcia and the Val di Chiana, Montepulciano offers postcard-perfect, 360-degree views of the Tuscan countryside—rolling green hills and golden fields dotted with cypress trees.
The town is best explored on foot. Its main street winds uphill for about 1.6 km, beginning at Porta al Prato and leading to the spectacular Piazza Grande. Here stands the Palazzo Comunale (City Hall), which recalls Florence’s Palazzo Vecchio—climb its tower for spectacular views. In the piazza, look for the historic well topped with the Medici coat of arms with six balls, reminder of Florence’s dominance.
Traditions keep Montepulciano vibrant and alive. Each August, the streets echo with the Bravio delle Botti, when teams from the town’s districts (contrade) roll 80 kg wine barrels up to the Duomo’s long staircase, the race’s dramatic finish line. During the same week, the cathedral’s unfinished brick façade serves as a backdrop for flag-throwing contests. By December, Piazza Grande transforms again, hosting one of Italy’s largest Christmas markets, complete with dazzling light projections that turn the square into a winter wonderland.
Just outside Montepulciano stands the Temple of San Biagio, a Renaissance jewel. Its travertine façade, glowing in the sunset, and its picturesque setting make it one of Tuscany’s most photogenic churches.
And then there’s the wine. Montepulciano is the home of Vino Nobile di Montepulciano, one of Tuscany’s most celebrated reds. To immerse yourself in its history, visit the spectacular Cantina de’ Ricci, whose soaring vaulted cellars have earned it the nickname “the Cathedral”. Or explore the historic cellars of Palazzo Contucci (free entry). For tastings and shopping, try Bottega del Nobile on Via Gracciano, just 100 meters from Porta al Prato. And if you don’t know where to begin, you can’t go wrong with the “ABC” winemakers—Avignonesi, Bindella, Boscarelli, Cesiro, Contucci—then continue with Dei, Il Macchione, or Sanguineto.
