Entering from Porta San Giovanni, the first stop on the itinerary is the Torture Museum. It houses a unique collection in the world of instruments designed to torture from all over Europe, which date back almost entirely to the 16th and 17th centuries. In addition to the famous Virgin of Nuremberg, the large sarcophagus filled with pointed nails, there are also the guillotine, the stretching bench, the impaling pole, the pillory, the inquisitorial chair and the chastity belt. Going up via San Giovanni you arrive at Piazza della Cisterna, one of the most beautiful squares in San Gimignano, which owes its name to the well that occupies the central part. Characterized by a triangular shape, it is surrounded by medieval palaces and towers. Noteworthy are the Salvestrini house, the Tortoli palace, the two Ardinghelli towers and the fifteenth-century Cortesi-Lolli palace.

Continuing on via Costarella, after a few steps you will reach Piazza del Duomo, which is overlooked by some of the most important buildings in San Gimignano. On the left is the Palazzo Comunale, which houses the historic seat of the Civic Museums. Also known as Palazzo del Popolo or Palazzo Nuovo del Podestà, it was built in 1288 and enlarged in 1323. On the first floor you can admire the ancient Council Hall, also known as the Sala di Dante, which features a famous cycle of frescoes by the Florentine painter Azzo di Masetto. On the second floor are the Podestà’s room and the Pinacoteca, where works of inestimable value created by artists of the caliber of Filippino Lippi, Benozzo Gozzoli and Pinturicchio are kept. From the Pinacoteca it is possible to access the Torre Grossa, from which you can enjoy a breath-taking view of the city.

Next to the Palazzo Comunale stands the Collegiate Basilica of Santa Maria Assunta, also known as the Cathedral of San Gimignano. The walls are covered with splendid frescoes depicting scenes from the New and Old Testament made by well-known painters of the Sienese school of the fourteenth century. At the bottom of the right aisle, it is also possible to admire the beautiful Chapel of Santa Fina, inside which the relics of the saint of the same name are preserved. Designed by Giuliano and Benedetto da Maiano in the 15th century, it presents a magnificent cycle of frescoes by Domenico Ghirlandaio, one of the most important masters of the Florentine school. The Museum of Sacred Art has been set up next to the Cathedral, in the ancient Dormitory of the Chaplains. Arranged on two floors, it includes liturgical furnishings and works from the churches and convents of the area.

Opposite the Cathedral stands the Palazzo Vecchio del Podestà, with the tower called Rognosa and an enchanting fresco by Sodoma. From Piazza del Duomo, a small road on the right of the church climbs towards the suggestive Rocca di Montestaffoli, from which you can observe an extraordinary view of the city and the surrounding countryside. Here the municipal centre for documentation and tasting of Vernaccia di San Gimignano wine has been set up, where, in addition to discovering the history of this wine, it is possible to participate in various tastings. Finally, the last stop on the itinerary is the Church of Sant’Agostino located in the homonymous square. Dating back to the 13th century, it has features of both Romanesque and Gothic architecture. Of particular interest is the exceptional cycle of frescoes by Benozzo Gozzoli with the Stories from the life of St. Augustine.