Itineraries for Your Trip to Arezzo
3 Days in Arezzo for First Timers
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 a number of iconic hill towns, including Cortona and Siena.
When I want to make a dash across the border from my home region of Umbria into neighboring Tuscany, I head straight to Arezzo. Here I can soak in authentic Tuscan culture and cuisine without having to elbow my way through tourist crowds, plus explore nearby attractions hassle-free. Here are my insider tips for three days in Arezzo and the surrounding Tuscan hill towns and countryside.
Set in the Apennine foothills, Arezzo has hot summers and nippy winters, with lots of rain in spring and fall.
If you only have time for one thing, linger in Arezzo’s postcard-perfect Piazza Grande main square.
Start your trip with a guided walking tour of the Arezzo’s cultural highlights. 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, head to a winery set in the rolling vineyards in the nearby countryside. Taste the area’s excellent vintages paired with Tuscan cheeses and meats.
Today, strike out for charming Cortona, made famous in Under the Tuscan Sun. Visit the historic center, including the Piazza Garibaldi and Piazza della Repubblica; art aficionados can add the Diocesan Museum and Church of San Domenico to see three works by Fra’ Angelico, all dating from 1436. If you have time, 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, and its quiet shores offer the perfect way to end the day. Set off with a sunset boat cruise to take in views of its surrounding hills from the water.
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.
Once you’ve taken in the cathedral from top to bottom, explore Siena’s grand historic center, including Palazzo Pubblico, Torre del Mangia, Basilica di San Domenico, and sweeping Piazza del Campo—site of the city’s rollicking 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.
