Arezzo

Arezzo is a beautiful town that sits atop a hill at the crossroads of four valleys: Val Tiberina, Casentino, Valdarno and Valdichiana. The 'Man of the El' was discovered here and found to date back to the Paleolithic era. In the 9th century BC, it became the Etruscan Arretium and rapidly turned into one of the most important cities in Tuscany, due to its strategic position along the Via Cassia. Today it is one of the wealthiest cities in Tuscany.

Even though the Medieval center was destroyed during World War II, Arezzo has plenty of monuments, churches and museums remaining that offer visitors a chance to step back into history. The Church of San Francesco is probably the most famous in Arezzo, with the incredible Early Renaissance fresco cycle by Piero della Francesca depicting the Legend of the True Cross. You should then head uphill to the Medicean Fortress, visit the Cathedral dedicated to San Donato, then back down to the Roman Amphitheater and the Church of San Domenico with the wooden Crucifix by Cimabue.

Nearby:
Visit the area of Valtiberina (Sansepolcro, Anghiari, Monterchi) the area of Setteponti (Loro Ciuffenna, Castiglion Fibocchi, Castelfranco) and Cortona, Castiglion Fiorentino

Distances:
Florence - 50 miles, Siena - 57 miles, Cortona - 19 miles

Cortona

One of the oldest hill towns in Tuscany, surrounded by 3,000 year old Etruscan walls, Cortona retains much of its history through its architecture, layers of history built upon the Etruscan core. The plain below Cortona is speckled with Etruscan tombs. But Cortona isn't just about the past; it is the setting for 'Under the Tuscan Sun' (book and movie) and has a thriving Expat community, which is quite involved with the city.

Cortona's Etruscan walls are incorporated into the medieval walls that surround its historic center. Inside the walls, you can wander the narrow medieval streets of Cortona's historic center. Near the walls, you'll often be rewarded with fantastic views of the valley below. Be sure to visit the century town hall and clock tower on one of Cortona's main squares, Piazza della Republica. There are cafes nearby for enjoying the piazza life and the 13th century Palazzo Pretorio on Piazza Signorelli is the Etruscan Academy Museum. Besides good Etruscan artifacts, the museum holds Roman remains, Renaissance and Baroque paintings, 15th century ivories, and a small Egyptian exhibit.

Nearby:
Visit Arezzo, Castiglion Fiorentino, Montepulciano, Pienza

Distances:
Siena - 45 miles , Arezzo - 19 miles, Florence - 64 miles