The Town of Fine Towers: A San Gimignano Walking Tour

San Gimignano’s 14 medieval towers pierce the Tuscan sky like stone skyscrapers, earning it the nickname “Manhattan of the Middle Ages.” On this walking tour, you’ll discover how this small hilltop town became extraordinarily wealthy in the 1200s and 1300s.

The tour starts in the central Piazza del Duomo. You’ll walk through elegant medieval squares and past imposing towers built by rival families to display their wealth and power. You’ll also discover the frescoed church where Michelangelo’s teacher once worked, and explore quiet residential streets where locals still live among these remarkable stone monuments. Along the way, you’ll learn why San Gimignano is the only Italian town that preserved so many towers when others demolished theirs.

You’ll stand beneath the best-preserved family towers in Italy, hearing how they served both as status symbols and defensive fortifications with retractable ladders and indoor escape routes. The tour ends at the austere Church of St. Augustine, home to important fresco cycles depicting the saint’s life transported into Renaissance Italy.

On this 40-minute tour, you’ll have a chance to:

• Admire the Torre Grossa, still the town’s highest tower at 54 meters, from the courtyard of the Palazzo del Popolo
• Learn about Vernaccia, the delicate white wine mentioned by Dante that became Italy’s first DOC in 1966
• Discover how the golden threads of saffron – once worth more than salt – made medieval merchants extraordinarily rich in the charming Piazza della Cisterna
• Climb the fortress of Montestaffoli for sweeping views over the town’s remarkable skyline
• Examine the Cugnanesi tower’s architecture to understand how medieval families connected their homes to these defensive structures

This tour reveals how a small medieval town became one of Tuscany’s most distinctive destinations. If you have time, try the world-champion gelato at Gelateria Dondoli afterwards.