Cortona has a rich history as one of the oldest hill towns in Tuscany. It was also prominently featured in the book and movie Under the Tuscan Sun by Francis Mayes, which turned it into something of a tourist attraction.
Cortona is a beautifully city, but like other Tuscan towns it can be expensive if you’re not prepared. Begin your trip by exploring the Etruscan tombs scattered around the entrance of town and take in the olive groves and Renaissance Church, all for free.

© Bartuchna | Dreamstime
Make your way to the center of town and the Via Nazionale, the only flat street in Cortona, where you’ll find a wonderful breakfast at Caffe Tuscher for a meal and coffee for less than $15.
From there, make your way to the Piazza della Republica, the heart of town, to take in a few of the sites and visit the local mom-and-pop shops selling goods and souvenirs. Nearby you’ll find the Museo dell’ Accademia Etrusca. An entrance fee of $12 will gain you access to rooms full of Etruscan, Roman, Renaissance and Baroque paintings, and even a small Egyptian exhibit.
It’s never too early for a good glass of wine, so head on over to La Bucaccia for a light meal and a drink. They have a wide selection of choices and the owner is known for his gregarious and delightful personality. It’s a bit on the pricey side, so expect to drop around $30 for a meal.

© Pavlos Rekas | Dreamstime
Afterward, walk to Cortona’s public gardens and the church of San Domenico to view a 15th-century altar piece and other beautiful works of art. Finally, take a stroll along Cortona’s Etruscan walls; you can get a view inside the narrow corridors along with spectacular sights of the surrounding hills from above.
End your evening with a traditional Italian meal and wine at the famous Osteria del Teatro. It’s beloved like locals and tourists and home to some of the most delicious antipasto around.
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