53km (32 miles) NE of Montepulciano; (53 miles) SE of Florence; 246km (153 miles) N of Rome

This lively little city on the eastern flanks of the Valdichiana is not as often visited as its more famous Tuscan neighbors, but get past that fairly unremarkable 20th-century perimeter—much of it built atop the rubble left by Allied bombings in World War II—and you’ll find an enticing medieval city of cobbled streets.

Arezzo’s rich cultural life has left it with a number of art-filled churches. Famous natives of Arezzo include not only Vasari but Piero della Francesca, from nearby Sansepolcro, the poet Petrarch (1304–74), and actor and director Roberto Benigni, who filmed parts of his 1999 Oscar-winning La Vita è Bella (Life Is Beautiful) here.

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Festivals and Fairs

Arezzo's famous antiques fair takes over the Piazza Grande and adjoining streets the first Sunday of each month and the preceding Saturday. More than 500 vendors come from around Italy to sell an appealing array of old furniture, silver, oil paintings, and other wares, at very good prices.

The Giostra del Saracino, a jousting contest between the four districts of the town, turns the clock back to medieval times twice a year in June and September. A lively procession through the streets to the accompaniment of trumpets and drums ends in Piazza Grande, where jousters on colorfully bedecked horses wield their lances against armor-plated dummies.

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