Chianti and San Gimignano: Exclusive Wine and Art Tour

Next, continue to San Gimignano, famously dubbed the “Medieval Manhattan” for its towering skyline. Enter through one of its historic gates – Porta San Matteo, Porta San Giovanni, or Porta Quercecchio—and step into a world where time seems to have stood still. As you explore its medieval streets, marvel at the 13 surviving towers that once symbolized the town’s wealth and power. The town’s historic center is a treasure trove of architectural and artistic wonders.

You’ll have ample free time to visit the highlights of the town at your own pace and according to your own interests: you will certainly want to stop at Piazza del Duomo, home to significant landmarks such as the Palazzo Vecchio del Podestà, the Palazzo Comunale, and the Collegiate Church of Santa Maria Assunta, which houses exquisite frescoes by renowned Tuscan artists. The town’s perimeter is equally captivating, featuring a series of historic churches adorned with stunning frescoes, such as Sant’Agostino, where Benozzo Gozzoli’s paintings are some of the greatest works of the early Renaissance.

For panoramic views of the Tuscan landscape, don’t miss a walk up to the Rocca di Montestaffoli, a 14th-century fortress surrounded by olive groves.

Don’t be fooled by the modest Romanesque facade of the town’s Duomo – inside splendor awaits, with breathtaking frescoes adorning almost every surface. On the left side, Bartolo di Fredi’s Old Testament stories unfold in rich detail, while the right side features the New Testament cycle attributed to Simone Martini’s followers.

Our journey through the nave reveals the dramatic Judgment Day fresco by Taddeo di Bartolo, commanding attention with its bold imagery. The transept hides more treasures, such as the Chapel of Santa Fina, where Ghirlandaio’s masterpiece continues to inspire, and the 13th-century wooden crucifix, radiating an almost mystical aura.

A short walk from Piazza del Duomo, we move towards the picturesque Piazza della Cisterna, a triangular square named after the ancient cistern. The lively piazza was once the heart of medieval life, bustling with markets, festivals, and even jousting tournaments. Surrounded by imposing medieval towers and historic buildings, each with its own story, the square exudes an atmosphere of timeless charm.

As we take in the details, Palazzo Tortoli, with its elegant 14th-century windows, and the mysterious Torre del Diavolo (Devil’s Tower), captures our imagination. According to local lore, the tower grew taller while its owner was away—an unexplained phenomenon attributed to the devil himself.