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

Cortona sits majestically on a green mountainside above terraced olive groves, stony yet inviting. It's 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. Its art treasures have always ensured a steady stream of tourists, but the huge popularity of Frances Mayes's book Under the Tuscan Sun (1996), about finding love whilst buying and renovating a villa just outside town, hurled Cortona from relative obscurity to the forefront of Tuscan tourism, especially after the tear-jerking movie starring Diane Lane was released in 2003. Expect serious crowds, especially in summer.