The 20 Most Breathtaking Medieval Italian Towns to Visit

Italy is home to countless historic treasures, many of which can be found in its medieval towns. With cobbled streets, fortified walls, ancient churches, and stunning castles, these towns offer visitors a chance to step back in time. Whether nestled in the rolling hills of Tuscany or perched atop rugged mountains, each town has a unique charm and story. Here’s a guide to the 20 most breathtaking medieval towns in Italy that transport visitors into a bygone era.

1. Sacra di San Michele, Piemonte

Overlooking the Susa Valley, Sacra di San Michele is an ancient abbey perched on Mount Pirchiriano. Founded in the 10th century, this mystical site inspired Umberto Eco’s The Name of the Rose. Its Romanesque architecture, panoramic views, and stone staircases make it a favorite destination for history enthusiasts and pilgrims.

Where to stay in Susa Valley

2. Castel del Monte, Puglia

Castel del Monte is a 13th-century castle located in Puglia, renowned for its unique octagonal shape. Built by Emperor Frederick II, it is a UNESCO World Heritage site and one of the finest examples of medieval architecture in Italy. The castle’s symbolic design and mysterious history attract countless visitors every year.

Where to stay in Castel del Monte

3. Siena, Tuscany

Siena, with its famous Piazza del Campo and Gothic cathedral, is a treasure trove of medieval art and architecture. The city is known for the Palio, a thrilling horse race held twice a year. Walking through Siena’s narrow streets, one can admire ancient frescoes, palaces, and charming cafes that bring medieval Italy to life.

Where to stay in Siena

4. Gubbio, Umbria

Nestled in the Apennine Mountains, Gubbio is one of Umbria’s most well-preserved medieval towns. The Palazzo dei Consoli, a grand Gothic palace, dominates the town’s skyline. Known for its ceramics and the Festa dei Ceri, a traditional festival, Gubbio is full of vibrant history and culture.

Where to stay in Gubbio

5. Monteriggioni, Tuscany

This enchanting walled town appears frozen in time. Located in the heart of Tuscany, Monteriggioni’s 13th-century walls and towers have remained intact for centuries. It’s a small town that can be explored within an hour, yet it offers an incredible glimpse into Italy’s medieval past.

Where to stay in Monteriggioni

6. Fenis Castle, Aosta

Fenis Castle in the Aosta Valley is a classic medieval fortress with towers, battlements, and frescoed walls. Built in the 14th century, the castle is renowned for its mural paintings and intricate architecture, making it a picturesque destination in the Italian Alps.

Where to stay in Fenis

7. Urbino, Marche

Urbino, a UNESCO World Heritage site, is home to the Renaissance art and architecture that influenced Italian culture. The Ducal Palace, a masterpiece of Renaissance design, houses the National Gallery of the Marche, which boasts works by Raphael and other Italian masters. Urbino’s rich history makes it a must-visit destination.

Where to stay in Urbino

8. San Gimignano, Tuscany

Known as the “Town of Fine Towers,” San Gimignano is famous for its skyline filled with 14 well-preserved medieval towers. A UNESCO World Heritage site, this town offers stunning views of the Tuscan countryside, along with charming piazzas, churches, and winding alleyways.

Where to stay in San Gimignano

9. Perugia, Umbria

Perugia, Umbria’s capital, is known for its medieval architecture and lively culture. The Palazzo dei Priori, a Gothic palace, and the Fontana Maggiore, a 13th-century fountain, are among its highlights. Perugia is also famous for its chocolate festival, making it a sweet addition to your travel itinerary.

Where to stay in Perugia

10. Bergamo, Lombardy

Divided into the historic “Città Alta” and the modern “Città Bassa,” Bergamo is a city of contrasts. The medieval upper city, surrounded by Venetian walls, features stunning architecture, cobbled streets, and the breathtaking Basilica di Santa Maria Maggiore. The fusion of old and new makes Bergamo an unforgettable destination.

Get your perfect stay in Bergamo

11. San Miniato, Tuscany

San Miniato, a small hill town in Tuscany, is famous for its truffles and medieval architecture. The Rocca di Federico II, a fortress with panoramic views, is a must-see. San Miniato’s annual white truffle festival attracts food lovers from all over the world.

Get your perfect stay in San Miniato

12. Civita di Bagnoregio, Lazio

Known as “The Dying Town,” Civita di Bagnoregio is an isolated hilltop village with a stunning view of the surrounding valley. Accessible only by a pedestrian bridge, this charming town faces erosion but continues to captivate visitors with its otherworldly beauty and ancient architecture.

Get your perfect stay in Bagnoregio

13. Sirmione, Lombardia

Located on the shores of Lake Garda, Sirmione is a romantic town with a 13th-century castle, Scaliger Castle, which overlooks the lake. Visitors can explore the town’s thermal baths, Roman ruins, and beautiful beaches. Sirmione is the perfect blend of history, relaxation, and natural beauty.

Get your perfect stay in Sirmione

14. Viterbo, Lazio

Known as the “City of Popes,” Viterbo was once a papal seat in the Middle Ages. The medieval quarter, San Pellegrino, is one of Italy’s best-preserved, with narrow streets, stone houses, and historic churches. The annual Santa Rosa Festival brings Viterbo’s medieval charm to life.

Get your perfect stay in Viterbo

15. Assisi, Umbria

Assisi, the birthplace of Saint Francis, is a spiritual destination renowned for its medieval architecture. The Basilica di San Francesco, adorned with frescoes by Giotto, is a UNESCO World Heritage site. Assisi’s serene ambiance and historical significance make it a popular pilgrimage site.

Get your perfect stay in Assisi

16. Montepulciano, Tuscany

Montepulciano, a hill town in Tuscany, is famous for its Renaissance buildings and world-class wine. The Piazza Grande, surrounded by medieval palaces, is a highlight. Wine cellars carved into the hillsides offer tastings of Montepulciano’s renowned Vino Nobile.

Get your perfect stay in Montepulciano

17. Republic of San Marino

The Republic of San Marino, one of the world’s oldest republics, is a medieval wonder with ancient towers, stone walls, and beautiful views of the Adriatic coast. The Three Towers of San Marino offer incredible panoramas, and the entire city-state feels like a step back in time.

Get your perfect stay in San Marino

18. Bologna, Emilia-Romagna

Bologna, with its rich history and vibrant university scene, boasts medieval architecture like the famous Two Towers, Asinelli and Garisenda. The city’s porticoes, lively markets, and traditional trattorias create an authentic Italian experience with a medieval backdrop.

Get your perfect stay in Bologna

19. Garfagnana, Tuscany

Garfagnana, nestled in the Apuan Alps, is a collection of medieval villages and castles surrounded by breathtaking natural scenery. This region offers a slower pace and opportunities for outdoor activities like hiking, making it ideal for those seeking both history and nature.

Get your perfect stay in Garfagnana

20. Bard, Aosta

The small town of Bard is dominated by the Forte di Bard, a fortress with spectacular views of the surrounding mountains. Bard’s charming streets, lined with stone houses and medieval architecture, transport visitors to a different era. The fortress, now a museum, offers fascinating exhibits on the region’s history.

Get your perfect stay in Bard

Italy’s medieval towns offer more than just beautiful views; they provide a rich tapestry of history, culture, and architecture that transports visitors to another time. From the hilltop monasteries of Sacra di San Michele to the serene shores of Sirmione, each town tells a unique story that speaks to Italy’s vibrant past. Whether you’re wandering through the cobbled streets of Assisi or admiring the towers of San Gimignano, these towns are a must-visit for any history lover or traveler seeking to experience the charm of medieval Italy.

Found something amazing? Spread the wonder and share it with your friends! 🥰