Arezzo is as Tuscan as you can get, both in spirit and in location. In addition to a Hollywood-ready medieval center, the town overlooks four valleys—Val Tiberina, Casentino, Valdarno, and Valdichiana—and is within striking distance of Cortona and Siena. Here are a few ways to see Arezzo and the finest Tuscan hill towns and countryside in three days.
Day 1: In and Around Arezzo
Get to know Arezzo’s handsome historic center and pretty countryside in a single day, beginning with a guided walking tour of the town’s cultural highlights in the morning. Take in the main Piazza Grande, lined with Vasari’s Renaissance Loggia and Romanesque apse of the Church of Santa Maria della Pieve, and stop by the Church of San Francesco and the cathedral to admire Piero della Francesca’s 16th-century frescoes. In the afternoon, wine lovers can tour a winery set in the rolling vineyards and taste the area’s excellent vintages, while foodies can learn how to create classic Tuscan dishes with a local chef.
Day 2: Cortona’s Simple Pleasures
Experience the charm of Cortona, made famous in Under the Tuscan Sun, with a themed walking tour of the historic center that includes locations featured in the book and film, such as Piazza Garibaldi and Piazza della Repubblica. Art aficionados can visit the Diocesan Museum and the Church of San Domenico to see three works by Fra’ Angelico, all dating from 1436. Afterwards, head outside of town to visit two elegant Renaissance churches: Giorgio Vasari’s domed Santa Maria Nuova and the Santa Maria delle Grazie al Calcinaio, home to the Madonna del Calcinaio image, said to perform miracles. Lake Trasimeno is just a few minutes away, its quiet shores offering a welcome break from sightseeing and the perfect way to end the day.
Day 3: Sightseeing in Siena
Spend your third day exploring stately Siena and its large yet perfectly preserved medieval center. Start at the cathedral complex with skip-the-line tickets to view the church, baptistery, museum, and library, taking in masterpieces by Bernini, Donatello, and Michelangelo. Afterwards, explore Siena’s grand historic center with a walking or Segway tour of highlights, including Palazzo Pubblico, Torre del Mangia, Basilica di San Domenico, and sweeping Piazza del Campo—site of the city’s rolicking annual Palio festival and horse race. Photography buffs will want to capture the views over the Crete Senesi landscape from the scenic overlook in Piazza del Mercato; most tours also visit local artisan workshops.