Cortona is one of the oldest hill towns in Tuscany and is featured in Francis Mayes's book Under the Tuscan Sun and followed by the movie. Cortona's medieval streets are pleasant to walk, and enjoy fabulous countryside views along the medieval town walls. Cortona has remnants of its pre-Roman Etruscan past, Renaissance artists Luca Signorelli and Fra Angelico, and Baroque artist Pietro di Cortona.
Piazza della Republica: The 13th-century town hall and clock tower are on one of Cortona's main squares, Piazza della Republica. There are cafes nearby to enjoy the piazza life.
Duomo: Cortona's Renaissance cathedral, built on the site of an Etruscan temple, has an 11th-century facade and beautiful 16th and 17th-century paintings inside.
Museo dell' Accademia Etrusca: In the 13th century, Palazzo Pretorio, the Etruscan Academy Museum, located on Piazza Signorelli. Besides good Etruscan artifacts, the museum holds Roman remains, Renaissance and Baroque paintings, 15th-century ivories, and a small Egyptian exhibit. It's closed on Mondays.
Museo Diocesano: This small museum holds outstanding artworks and a decorated Roman sarcophagus.
San Domenico: Near the public gardens, the church of San Domenico has an entirely intact 15th-century altarpiece and works by Fra Angelico and Signorelli.
San Francesco: The Church of San Francesco, built in 1245, holds a Pietro di Cortona painting and the remains of Signorelli.
Cortona's Walls: Cortona's Etruscan walls are incorporated into the medieval walls surrounding its historic center. Inside the walls, you can wander the narrow medieval streets of Cortona's historic center.
Le Celle di Cortona: A Franciscan convent holds the Spartan cell where St. Francis stayed when he preached there in 1211. It's about a 45-minute walk through the woods outside Cortona's walls. You can visit The church and gardens for free.
The 16th-century Medici fortress: Above Cortona has excellent views over Lake Trasimeno. Follow via S. Margherita uphill past lovely gardens to the fortress.
Food and Wine in Cortona:
Cortona has good restaurants serving typical Tuscan food. Enoteria, on Via Nazionale, is a good place for wine tasting. Also on Via Nazionale is the Antica Drogheria with wine, grappa, and health products of the Camaldolesi monks. You'll find picnic supplies in several stores in town, and on Saturdays, there's a market in Piazza Republica. On August 15 is the Sagra della Bisteca (beef steak festival).
Cortona Orientation: The road to Cortona from the valley starts near the Melone Etruscan tombs. On the way up the hill, you'll pass more Etruscan tombs, olive groves, and the Renaissance Church of Santa Maria Delle Grazie al Calcinaio. If you're driving, look for parking near the top of the hill as soon as possible. If you're arriving by bus, you'll arrive in Piazza Garibaldi, a prime-view spot. From the square, walk along Via Nazionale, Cortona's only flat street, to Cortona's center, Piazza Republica and Piazza Signorelli.