4Cortona

A more than 2,700-year-old Etruscan town, Cortona is famous for its glorious hilltop views (and for being where “Under the Tuscan Sun,” starring Diane Lane, was filmed). At 1,968 feet above sea level, you can see all the way to Lake Trasimeno.  

Its steep, tiny alleys lead up to the main piazza, where you can savor a glass of local Vino Nobile di Montepulciano. Steaks from Chianina cattle, bred nearby, are commonly served in restaurants, as is cured wild boar meat. And shops specialize in local extra virgin olive oil as well as a variety of handcrafted goods made of leather, ceramic, or clay.

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