Montepulciano is the highest of Tuscany’s postcard-perfect medieval hill towns, offering bird’s-eye vistas over the surrounding Val d’Orcia and Val di Chiana. Wine lovers travel here to sample Vino Nobile produced in the area’s world-class cellars and winery tours and tastings top the to-do list. Montepulciano’s intact medieval old town is also a star attraction, peppered with highlights like the historic town hall, a terracotta altar by Andrea della Robbia in the Church of Santa Maria delle Grazie, and the Madonna di San Biagio sanctuary just outside of town.
If you drive to Montepulciano, you’ll have to leave your car in paid parking lots around the town, as only residents are allowed to drive within the walls. If you want to arrive by train from a major city, take a fast train to Chiusi and then a bus to the town. Once there, use the pedestrian shortcuts (an elevator and stairs) to the historic center, and then explore the hilly streets on foot.
In the off-peak months of November through March, most Montepulciano restaurants and tourist amenities are closed. Around Easter they reopen, and the village stays lively with visitors through the end of summer. If you want to avoid the throngs of day-trippers and stifling heat, consider the shoulder months of May, June, and September.
At the end of August, the annual Bravio delle Botti—a historic barrel racing event—is held in Montepulciano. Crowds gather to watch burly local men compete by rolling huge wooden wine barrels up the steep old town streets. The race takes place amid other colorful events including medieval costume parades, flag waving, and decorated streets.
