Cortona is a compact medieval hill town in eastern Tuscany, perched on a steep slope with sweeping views over the Val di Chiana to Lake Trasimeno. It became internationally famous as the setting for Frances Mayes' memoir Under the Tuscan Sun, but the town's appeal long predates the book — the Etruscans built walls here that still stand.
The Piazza della Repubblica and its surrounding streets are full of small restaurants, wine bars and artisan shops. The Museo dell'Accademia Etrusca on Piazza Signorelli houses an impressive collection of Etruscan artefacts, and the Museo Diocesano across the cathedral square holds Fra Angelico's Annunciation. The quiet lanes above the centre lead to the Basilica di Santa Margherita and the Medici fortress, both offering panoramic views. Outside the walls, the Renaissance Santa Maria delle Grazie al Calcinaio and the Etruscan tombs at Il Sodo reward a half-day's exploration in the surrounding countryside.
Cortona is small enough to explore in half a day, but the atmosphere — and the wine — tend to make people stay longer.