San Gimignano (SI) – 11 km – 7 miles

The charm of San Gimignano: The Manhattan of the Middle Ages  

Discover San Gimignano, a town nestled in the hills of Val D’Elsa, just a few kilometres from Siena. Known as the ‘Manhattan of the Middle Ages’ for its many medieval towers, this town offers a unique experience with an historic centre full of attractions, all of which can be explored on foot.    

Historical Towers: Symbols of San Gimignano

Arriving in San Gimignano, it is impossible not to notice them. They all spring up from the heart of the town centre. Of the original 72, only 14 now remain standing, but these dominate the urban landscape. The tallest is Torre Grossa, which towers in the centre. Built in the 1300s, 54 metres high, this tower is one of the few with interiors that can be visited and where you can climb to the top. Torre Grossa offers a breathtaking view of the Tuscan countryside and Chianti vineyards and even of the Apuan Alps on a clear day.    

The squares of San Gimignano

The two most famous squares are undoubtedly Piazza del Duomo and Piazza della Cisterna

Piazza del Duomo, as its name suggests, was the beating heart of the political-religious life of the then medieval city. The two fulcrums were the Palazzo del Potestà, which today houses the Museo Civico and the cathedral of the same name. In the Museo Civico one can admire several works by artists from the Florentine and Sienese schools, such as Pinturicchio. With the same ticket, you can climb up to the top of the Torre Grossa to breathe in the air of the Tuscan countryside. The Duomo, also known as the Basilica Collegiata di Santa Maria Assunta. This building has almost a thousand years on its shoulders: it is estimated, in fact, to have been erected in 1056 but not consecrated until 1148. A symbol of Romanesque architecture, the Cathedral of San Gimignano houses inside frescoes by painters of the Sienese school such as Bartolo di Fredi and Taddeo di Bartolo.     

Piazza della Cisterna, on the other hand, was mainly used for markets, festivals and tournaments. It takes its name from the cistern below, built in 1287, and is still considered one of the most beautiful medieval squares in the world. One of the most striking constructions overlooking the beautiful square is the Torre del Diavolo (Devil’s Tower), one of the fourteen towers that appears to be the work of the devil himself.

Casa Salvestrini also overlooks Piazza della Cisterna, directly opposite the well. This tall and imposing building, now used as a hotel, is shrouded by a few climbing plants that bloom in fine weather, giving the building a poetic hue.    

The Walls of San Gimignano: Witnesses of Time

The Walls of San Gimignano are 2176 metres long. This work of military architecture was built in stages. The first one seems to have been erected at the end of the 10th century, while the second dates back to the 12th century, when trade was beginning to flourish thanks to the nearby Via Francigena. The Walls surround the entire city with five main gates that welcome visitors to this medieval jewel. A journey through these walls is a leap back in time, an unmissable experience for any lover of history and architecture. The five main gates (clockwise from the south):

Porta San Giovanni (on the Via Francigena towards Siena)

Porta Quercecchio (with simpler forms)

Porta San Matteo (on the Via Francigena towards Pisa

Porta San Jacopo

Porta delle Fonti