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).

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.

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.