5 Picturesque Towns in Tuscany You Won’t Want to Miss

Tuscany’s picturesque towns are an architecture and art lover’s paradise. Here are our Favourite Five.

San Gimignano

Renowned for its medieval charm and architectural wonders, San Gimignano is a must-visit destination in Tuscany. This UNESCO World Heritage site is famous for its well-preserved towers, which create a unique skyline often referred to as the “Medieval Manhattan.”

The town is home to the Collegiate Church of Santa Maria Assunta, built in the 13th and 14th centuries. Inside, you can admire renowned frescoes such as ‘Last Judgement’ and ‘Stories from the New Testament.’

San Gimignano is one of Tuscany’s most popular small towns, so expect to encounter quite a few crowds, especially during peak tourist seasons.

Pienza

Often called the “ideal city of the Renaissance,” Pienza epitomises Renaissance beauty. This hidden gem is nestled between Montepulciano and Montalcino in the historic Val d’Orcia region, which is also a UNESCO World Heritage site. Pienza was transformed by Pope Pius II into a model Renaissance town in the 15th century.

Stroll along Corso Il Rossellino, the main street, and visit the Diocesan Museum to see the pope’s embroidered cape and Flemish tapestries.

The town is also known for its delicious pecorino cheese, which you can sample in local shops.

Montepulciano

The picturesque village of Montepulciano, over 1,500 years old, has long attracted architecture and wine enthusiasts. This hilltop town offers a perfect blend of Renaissance and medieval architecture. Wander through its cobbled streets, enjoy a coffee in Piazza Grande, and marvel at the stunning palaces and churches.

Montepulciano is surrounded by vineyards producing the famous Vino Nobile di Montepulciano, a highly regarded red wine.

For breathtaking vistas of the Tuscan countryside, visit the San Biagio church, an exquisite example of Renaissance architecture. The annual Bravio delle Botti, a traditional barrel-rolling race, is a unique event that showcases the town’s vibrant culture!

Volterra

Perched on a hilltop with views over the surrounding valleys, Volterra is a must-visit for art and architecture lovers. This ancient town has a history dating back to the Etruscan period, over 3,000 years ago. It is home to 6th-century palaces and thousand-year-old Etruscan tombs, including the well-preserved Etruscan Arch.

Volterra’s Roman Theatre, dating from the 1st century BC, is another highlight. The town is known for its alabaster crafts, which you can purchase in local shops. Because Volterra is less well-known than other Tuscan towns, you’ll likely encounter fewer crowds and enjoy a more peaceful experience in its small shops and restaurants.

Arezzo

Located in eastern Tuscany, the delightful town of Arezzo is celebrated for its stunning museums, the Medici Fortress, and the breathtaking frescoes in its hilltop church. Inside the beautiful Romanesque church of Santa Maria della Pieve, you’ll find magnificent artworks by Piero della Francesca, including the famous fresco “The Legend of the True Cross” in the Basilica of San Francesco.

Try the famous ‘ribollita,’ a traditional Tuscan vegetable soup, before visiting the Casa Vasari and Casa del Petrarca house museums. Arezzo’s monthly antiques fair is one of the largest and most famous in Italy, attracting collectors from all over the world.

These five towns each offer a unique glimpse into Tuscany’s rich history, culture, and stunning landscapes. Whether you’re an art lover, history buff, or simply looking to enjoy the scenic beauty of the region, these towns should not be missed on your Tuscan adventure.

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