Travelling south from Arezzo you enter the Valdichiana, reclaimed swampland that is now prosperous farming country and vineyard, of which the hill-town of Cortona overlooks. From the valley floor, a 5km-long road winds up through terraces of vines and olives to the ancient Cortona, whose heights survey a vast domain: the Valdichiana stretching westwards, with Lago Trasimeno visible over the low hills to the south.

Via Nazionale is the only horizontal street in the centro storico, and the steep streets of Cortona are more or less untouched by modern building: limitations of space have confined almost all later development to the lower suburb of Camucia, which is where the approach road begins.

Even without its monuments, charming piazzas and art treasures, Cortona would be a good place to rest up, with decent hotels and excellent restaurants.

Until the mid-1990s, Cortona didn’t get much tourist traffic, but in recent years, the town’s popularity has increased markedly, in the wake of Frances Mayes’ Under the Tuscan Sun and Bella Tuscany, books that continue to entice coachloads of her readers to the town.

Top image: Cortona, Italy © cristapper/Shutterstock

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updated 26.04.2021

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