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Cortona

Cortona’s appeal lies in its lofty setting, splendid views and medieval mood. Set close to the Umbrian border, 30 km south of Arezzo, Cortona is one of the most delightful hill towns in Tuscany. It was founded by the Etruscans, colonised by the Romans, and, after its sale to the Florentines in 1409, thrived under the Grand Duchy of Tuscany. Cortona is perched majestically on a ridge of Monte Sant’Egidio, dominating the Val di Chiana. The approach road winds through terraced olive groves and vineyards, past villas, farms and monasteries.

Cortona is a tourism hotspot so its over-popularity is a given. The city’s slow burn was accelerated after the town found fame in Under the Tuscan Sun, a book which led to a film and a summer festival. Even so, once beyond the main squares, the crowds thin out. Luckily, there are enough quaint inns to restore any grumpy spirits.

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