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Perched on a hillside overlooking a vast plain in Tuscany, the charming small town of Cortona has a distinctly Medieval air, although its origins go back to Etruscan times, and it boasts an exceptional historical and archaeological heritage. Walk the steep, narrow streets, admire the nicely-preserved Etruscan walls and gateways, visit the 13th-Century Cathedral (Duomo), the church dedicated to the town’s patron saint, Santa Margherita, and the remarkable Franciscan convent Eremo Le Celle, which was founded by St. Francis himself. You can also shop for antiques, handicrafts and olive oil, and sample traditional Tuscan specialties such as panzanella, minestra di pane, trippa and castagnaccio, accompanied by a glass of excellent Tuscan merlot, syrah or sangiovese.