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The perfect Tuscan town

Magnificently situated, with olives and vineyards creeping up to its walls, Cortona commands enormous views over Lake Trasimeno and the plain of the Valdichiara. Its two fine galleries and scattering of churches are relatively unvisited, while its delightful medieval streets are a pleasure to wander for their own sake. 

Known by some as both ”Mother of Troy and Grandmother of Rome,” tradition claims Cortona was founded by Dardanus, the founder of Troy (after whom the Dardanelles are named). While fighting a local tribe, he lost his helmet (corythos) on a hill overlooking the plains below. In time, as a town grew on this same hill, it took the name Corito after the missing helmet.

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By the 4th century the Etruscans had built the first set of town walls, whose cyclopean traces can still be seen in the 2-mile sweep of the present fortifications. A member of the Etruscans’ 12-city Dodecapolis, it became one of the federation’s leading northern cities. An important consular road, the Via Cassia, which passed the foot of its hill, maintained the town’s importance under the Romans.


Medieval fortunes waned, however, as the plain below reverted to marsh. After holding out against neighbours like Perugia, Arezzo, and Siena, the commune was captured by King Ladislas of Naples in 1409 and sold to the Florentines two years later.

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Cortona’s steep streets make you pay for your pleasure, but any amount of puffing and panting is worth it to enjoy their views and medieval vignettes. Only one lane is level: the main Via Nazionale (linking’ Piazza Garibaldi and Piazza della Repubblica), referred to by locals as the Ruga Piana (Flat Street).

Areas well worth seeking out include Via Guelfa and Via Ghibellina, the main streets of the old town, both sprinkled with a mixture  of medieval and Renaissance architecture; Via Janelli, a picturesque thoroughfare of 14th-century timber-framed houses below Piazza del Duomo; and Via Maffei, lined with a parade of 16th-century Renaissance palazzi.


Visit the Fortezza Medicea and the public gardens near San Domenico for Cortona’s best views. Come at dusk, when lights twinkle across the huge plain below the town.

At Tuoro sul Trasimeno, just a few miles east of Cortona, you can visit the site of one of antiquity’s most famous battles. In 217 bc, Hannibal and his army defeated a Roman army under the consul Flaminius. Some 16,000 Romans were killed after a cunningly planned ambush. A drive and a marked trail have been laid out around the site.

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