Perched above vineyards and cypress-tree groves in the Italian province of Siena, Montepulciano is the biggest and highest medieval hill town in southern Tuscany. Panoramic views of the Val d'Orcia countryside render it a perfect setting for movies like The English Patient and Under the Tuscan Sun, but it is most famous for its Vino Nobile di Montepulciano, a red wine made primarily from Sangiovese grapes. The town, lined with Renaissance palaces and churches, centers on Piazza Grande, where the Bravio delle Botti barrel race takes place every August. Food lovers will especially enjoy shopping in the Centro Commercial Naturale, visiting the olive mill, and learning how to make pici pasta with flour from local wheat at the Il Sasso school for language and culture.
Uncork: The celebrated reds at the Consorzio del Vino Nobile di Montepulciano, the local wine consortium made up of more than 70 producers, and its Enoteca Wine Shop in the historical Palazzo del Capitano on Piazza Grande.
Pair: Sample Pecorino cheese, meat, honey, and olive oil in the town's cantines (wine cellars), which are often linked by underground tunnels. Local favorite Cantine Contucci, in the 13th-century cellars of the Palazzo Contucci, is open for tastings every weekday.