Cortona

With olive trees and vineyards creeping up to its walls, pretty Cortona—popularized by Frances Mayes's Under the Tuscan Sun—commands sweeping views over Lake Trasimeno and the plain of the Valdichiana. Its two galleries and churches are rarely visited; its delightful medieval streets are a pleasure to wander for their own sake. The heart of town is formed by Piazza della Repubblica and the adjacent Piazza Signorelli; both contain pleasant shops to browse in.

Cortona is considered one of Italy's oldest towns—popularly known as the "Mother of Troy and Grandmother of Rome." Tradition claims that it was founded by Dardanus, also the founder of Troy (after whom the Dardanelles were named). He was fighting a local tribe, so the story goes, when he lost his helmet (corythos in Greek) on Cortona's hill. In time a town grew up that took its name (Corito) from the missing headgear. By the 5th century BC the Etruscans had built the first set of town walls, whose cyclopean traces can still be seen in the 3-km (2-mi) sweep of the present fortifications.