Must-Visit Tuscan Villages

Montepulciano is a charming hill town in Tuscany. Walk the streets to get a feel for its appeal. On the outskirts of town visit San Biagio, a 16th-century church. This late-Renaissance building was constructed on the site of a pre-existing Palaeochristian pieve (a type of church) dedicated to Saint Mary and subsequently to Saint Blaise. By the early 16th century the pieve had fallen into ruin, its remains including a wall with a fresco of the Madonna with child, and Saint Francis, from a 14th-century Sienese painter. The church today has a circular plan with a large dome over a terrace and a squared tambour. The exterior, with two bell towers, is built in white travertine. It’s a lovely church worth the hike from the town center.

One of the most important cities during the Etruscan period, then later made rich by its goldsmith traditions, this city, just a short drive southeast from Florence, is something of an insider’s favorite when visiting Tuscany. With fewer crowds, you’ll have more room to breathe while exploring sites like the Church of San Francesco (with its stunning early-Renaissance frescos by Piero dell Francesca), the ruins of the Roman amphitheater, the Medicean Fortress, and the Church of San Domenico, home to a wooden crucifix by Cimabue. Arezzo is also a favorite among treasure seekers, as it’s home to a number of well-stocked antique shops and one of the best antiques fairs in Tuscany. Running since 1968, the latter takes place the weekend of the first Sunday of each month, and features over 500 vendors and up to 30,000 shoppers looking to score a find. Taking place July to September, the Terre d’Arezzo Music Festival also draws big crowds to the piazza with its calendar of classical concerts and opera performances.

While wine production has been a part of Montalcino life for centuries, it took the 1888 creation of Brunello di Montalcino—a gorgeous twist on Chianti blends made with 100 percent Sangiovese grapes—to put the medieval town’s name on everyone’s lips. Wine fans will delight in visiting area vineyards and producers, many still small and family-owned, and sampling vintages both at the source and in local bars. If you’re not a drinker, never fear: There’s plenty else in the fairy-tale town that will charm you, including the Piazza del Popolo main square, with its Gothic loggia; the 14th-century Rocca fortress, boasting breathtakingly vast views from its ramparts (a hotspot during sunset); and the Museo del Vetro, a glass museum set inside a former castle that showcases delicate works by the ancient Egyptians on down to modern-day Venetians. Stroll the maze-like cobblestone streets, popping into the small shops and cafés, to get a feel for the place. Better yet, visit during a festival; among the annual celebrations are Montalcino Honey Week in September and the Jazz & Wine Festival each July.