Arezzo Travelers Recommend

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.

With two days in Arezzo, not only can you enjoy the town’s notable art, architecture, and vibrant, lived-in historic center, but you’ll still have time left over to discover the quintessentially Tuscan town of Cortona, well-known to fans of Under the Tuscan Sun. Here’s how to combine them for two days of Tuscan discovery.

Day 1: Authentic Arezzo

Morning: Begin by taking in the cultural highlights in Arezzo, home to important medieval and Renaissance palaces and churches. Take a guided walking tour of the historic center to discover masterpieces such as Vasari’s elegant Loggia lining the Piazza Grande and Piero della Francesca’s magnificent 16th-century frescoes in the cathedral and Church of San Francesco.

Afternoon: Set in the heart of Tuscany, Arezzo is a prime spot to sample the region’s iconic food and wine; a hands-on cooking class in town or the surrounding countryside is a fun way to learn how to prepare classic Tuscan dishes. Oenophiles can instead head to the vineyard-covered hills for a winery tour and tasting.

Night: Enjoy the charm of Arezzo as the sun sets by heading to the Medici fortress above town for views over the valley, or relaxing at a sidewalk restaurant or café in the Piazza Grande. Photography enthusiasts can capture this and other striking Tuscan scenes during a nighttime photography walking tour in the historic center.

Day 2: Captivating Cortona

Morning: Cortona may be half the size of Arezzo, but it rivals its neighbor in scenic charm. Explore the medieval town center made famous in Under the Tuscan Sun —the bestseller later made into a film—by joining a themed walking tour through its pocket-size squares and tiny churches, including San Damiano, frescoed by Fra’ Angelico.

Afternoon: With its popularity as a tourist destination, it’s no surprise that Cortona is thick with excellent eateries. You can linger over lunch or, better, learn to make the area’s delicious dishes at home by joining a cooking class in town. If you’d rather spend a few hours at the beach, the placid waters of Lake Trasimeno are just minutes away.

Night: Your Tuscan immersion is drawing to a close, so be sure to toast your final evening by watching the sun set over the valley and Lake Trasimeno. One of the most panoramic spots in town is outside the pretty cathedral, with a sweeping view over the hills of Tuscany and neighboring Umbria.

Arezzo’s historic center is so meticulously preserved that it was the setting for the Academy Award–winning film Life Is Beautiful. Though its art and architecture are a delight to explore, this small Tuscan city remains refreshingly authentic, bustling more with locals than tourists. Here’s how to soak up the atmosphere in just one day.

Morning: A Historic Center Straight from Central Casting

It’s no surprise that Arezzo was chosen to play the role of the quintessential Tuscan town for Roberto Benigni’s 1997 hit film. With its mix of rustic medieval and elegant Renaissance architecture, lively main Piazza Grande, and friendly small-town character, this vibrant city in the hills southeast of Florence was typecast. The compact historic center can be easily visited in a morning; join a private guided walking tour to fully appreciate Arezzo’s architectural treasures such as the 16th-century Loggia Vasariana and the Romanesque Church of Santa Maria della Pieve, as well as masterpieces painted by Piero della Francesca in the 1500s to decorate the Church of San Francesco and Arezzo Cathedral (Duomo di Arezzo).

Afternoon: Tuscan Cuisine in and Around Arezzo

Tuscany is synonymous with excellent food and wine, and Arezzo is set in its culinary heart. Use your afternoon to discover the secrets to traditional Tuscan cuisine with a hands-on cooking class in the town center or a country estate. Most classes pair a practical lesson with an informal meal featuring the Tuscan classics you’ve prepared together. Wine lovers can opt for a winery tour and tasting instead, with a jaunt to Arezzo’s vineyard-covered hills. Alternatively, spend the afternoon exploring the nearby hill town of Cortona with a guided walking tour or local cooking class.

Night: Arezzo Under the Stars

Arezzo is lovely by day, but after the sun sets the city takes on a magical air. Shutterbugs can capture this evening glow by taking a photography walking tour through the historic center to experiment with different night-photography techniques, light settings, and framings of the city’s medieval monuments strikingly illuminated after sunset. Others can simply settle in at one of the animated restaurants or cafés lining Piazza Grande to people watch over a relaxing meal or glass of Tuscan wine.