31km (19 miles) NE of Montepulciano; 34km (22 miles) S of Arezzo; 105km (63 miles) SE of Florence; 194km (120 miles) N of Rome

Draped across a green mountainside above terraced olive groves, austere-looking Cortona is a steep medieval city, where cut-stone staircases take the place of many streets, and views over the wide Chiana Valley stretch south to Umbria's Lake Trasimeno. Cortona has truly punched above its artistic weight; it spawned (among others) the great pre-Michelangelo painter Luca Signorelli and the early-17th-century painter/architect Pietro da Cortona.

Cortona was already a thriving city by the 4th century B.C., when it was one of 12 cities that formed the Etruscan confederation. New finds at Melone II, one of several Etruscan tombs dotting the hillside and valley below the town, suggest it may have been an even more important center than previously believed.

Even though it was long in a fairly undervisited corner of Tuscany, Cortona never succumbed to the all-too-common fate of becoming a dusty abandoned backwater. It retained a good bit of passeggiata action most evenings on the Rugapiana ("flat street," a nickname for Via Nazionale, the only road in town that even comes close to fitting that description), and in summer, the city hosts a modest outdoor film festival in the Parterre Gardens behind San Domenico. In recent years, the book and film Under the Tuscan Sun have brought waves of appreciative fans to town, but Cortona has survived the onslaught. The somber streets and stage-set piazzas are a bit more crowded in summer than they once were, but the town’s appeal is as strong as ever and includes some significant art treasures and romantic misty views over the wide Valdichiana.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.