San Gimignano: Exploring the town of medieval towers

​San Gimignano, one of the most charming medieval towns in Tuscany​, is world-renowned for its iconic towers, which once symbolised the power and wealth of local noble families. This architectural gem, located nestled at the heart of the province of Siena, has preserved its medieval urban layout and offers visitors an authentic experience steeped in history, art, and nature. Wandering through its cobbled streets and admiring its picturesque squares truly feels like stepping back in time, into a place where time seems to have stood still.

The Timeless Charm of the Middle Ages: San Gimignano's must see

One of the main reasons to visit San Gimignano is certainly its unique skyline, characterized by its famous medieval towers. At the height of its splendor, the town boasted no fewer than seventy-two towers, built by wealthy families to display their status. Nowadays, only fourteen of them are left– still enough to provide a spectacular and unmistakable sight.

The towers not to be missed include:

• Torre Grossa: 54 meters of height, it’s the tallest tower and offers a breathtaking view of the surrounding countryside.

• Torre Rognosa: One of the oldest and most atmospheric, dating back to the 13th century.

• Torre del Diavolo: Its curious name, which literally means the devil’s tower, is tied to mysterious legends still handed-down by locals. ​​

The city center of San Gimignano revolves around two beautiful squares: Piazza della Cisterna and Piazza del Duomo, where you’ll find the Dome of San Gimignano (or Collegiata di Santa Maria Assunta) and the Town Hall (Palazzo Comunale) – both to be considered must-sees for those interested in the town’s artistic heritage. Inside the Collegiata, you can admire masterpieces by artists such as Benozzo Gozzoli and Domenico Ghirlandaio.

For those who enjoy walking and panoramic views, a visit to the Rocca di Montestaffoli is essential. This ancient fortress offers one of the best viewpoints in town, with a 360-degree view over the Tuscan hills and Vernaccia vineyards.

The Rocca also hosts various events, including the prestigious Vernaccia Wine Festival, celebrating this refined white wine.

The Civic Museum of San Gimignano, housed in the Town Hall, features a rich collection of artworks ranging from the Middle Ages to the Renaissance. Here, you’ll find frescoes, paintings, and sculptures by artists such as Filippino Lippi and Pinturicchio. The museum also allows visitors to climb Torre Grossa, offering yet another incredible view over the town and its rolling hills.

Events and Festivals in San Gimignano

San Gimignano is a vibrant town, hosting cultural events and traditional festivals all year round. One of the most anticipated is the Ferie delle Messi, a medieval re-enactment held each summer, transforming the town into a lively stage for parades, knightly tournaments, medieval markets and performances. During the festival, visitors can fully immerse themselves in the medieval atmosphere, sampling traditional food and enjoying shows by musicians and street artists.

The town also hosts wine-related events such as the Festa della Vernaccia, a local festival where you can discover the secrets of this esteemed white wine, take part in guided tastings and tour local wineries.

Wine and Food Experiences: Vernaccia and local flavours

In addition to its artistic and architectural heritage, San Gimignano is a must-visit for food and wine lovers. The area is famed for producing Vernaccia di San Gimignano, a DOCG white wine appreciated for its fresh, mineral notes. Visiting local wineries offers a chance to taste this unique wine alongside typical regional products such as Tuscan pecorino cheese, Cinta Senese salami, and high-quality extra virgin olive oil. Wine shops and restaurants throughout the town also serve traditional dishes like ribollita, pappa al pomodoro, and the famous “Fiorentina” steak.

Discovering the Tuscan countryside: where to stay in San Gimignano​

The surroundings of San Gimignano offer numerous alternatives for those who enjoy outdoor activities. The hills surrounding the town are excellent for hiking, cycling or horseback riding through idyllic and unspoilt landscapes. Exploring the Tuscan countryside in these areas also allows you to get to know wonderful farmhouses, where you can enjoy unique experiences.

Among the must-see venues, the Relais Villa Grazianella by Tenute del Cerro in Acquaviva di Montepulciano, offers maximum comfort, including suites, a restaurant and a swimming pool, along with authentic experiences… and renewed ones! In fact, here, in the land of Vino Nobile di Montepulciano, Tenute del Cerro’s new wine cellar is being relit, ready to welcome enthusiasts and curious ones. A unique opportunity to explore completely renovated environments, such as the fascinating barrel cellar and the elegant Aquarium Room, designed to offer moments of authentic connection with the world of wine.

Near San Gimignano, embedded in a wild and evocative landscape, is Tenuta di Monterufoli​, our estate located between Val di Cecina and Val di Cornia. Encircled by centuries-old forests, former mines and thermal springs, this estate offers an authentic dive in the wildest soul of Tuscany. It is the ideal place to combine off-road or e-bike experiences and exc​​​ursions with tastings of Vermentino di Toscana, amidst moments of relaxation in contact with nature, in a setting that is also ideal for motorcyclists, photographers and curious travellers.

For photography or motorcycling enthusiasts​, then, the surroundings of San Gimignano are a picture perfect setting: the rolling hills, cypress trees dotting the landscape, golden fields and lush vineyards offer unforgettable views, especially during sunset hours.​

San Gimignano and beyond: must-see surroundings​

San Gimignano is an optimal starting point for exploring other places in Tuscany, world-famous for their historical and gastronomic heritage. These include:

● Volterra​, renowned for its Etruscan history and charming historic centre.

● Certaldo, the birthplace of Giovanni Boccaccio, famous for its well-preserved medieval high part.

● Montalcino, perched among the hills of the Val d’Orcia and known throughout the world for its Brunello wine.

● Monteriggioni, a small fortified village surrounded by still intact medieval walls, offering a plunge into the past.

These towns, within easy reach of San Gimignano, are perfect for one-day trips, where one can explore new corners of Tuscany and savour local specialities. Ready to set off for an unforgettable weekend?