How to Spend 1 Day in San Gimignano

Soaring high above the medieval center of San Gimignano, the town’s 14 towers form one of the most remarkable skylines in Tuscany. This UNESCO World Heritage Site hill town is beloved for its intact historic center, excellent food and wine, and endless views over the pastoral countryside. Here’s how to experience its singular appeal in just one day.

Morning: Historic Center

The compact historic center of San Gimignano is considered one of the most enchanting in Tuscany, with medieval streetscapes virtually frozen in time since the town’s 14th-century heyday and more than a dozen of its original 72 towers still standing. Join a small-group or private walking tour to appreciate gems such as the Large Tower (Torre Grossa) and the Collegiate Church of Santa Maria Assunta. Stroll through Cathedral Square (Piazza Duomo) and Cistern Square (Piazza della Cisterna), take in the medieval city walls, and explore the ruins of the 16th-century fortress while learning about the rise and fall of this town along the ancient Via Francigena. 

Afternoon: The Wine Country

One of the biggest draws of San Gimignano is its captivating setting deep in the Tuscan hills, surrounded by some of the region’s most prestigious wine country. Set off in the afternoon to explore the countryside and sample wine at nearby wineries. For a lighthearted twist, you can tour the vineyard-covered hills by Italy’s iconic Fiat 500 car or Vespa scooter. Dedicated gourmands can also opt for a cooking class or truffle hunt followed by a cooking lesson to learn how to prepare Tuscan classics and enjoy the results during a celebratory dinner. Alternatively, head farther afield in the afternoon to visit the historic town of Siena, home to the famed Palio, or Volterra, with its fascinating Etruscan history. 

Night: The Flavors of Tuscany

Cap off your day in San Gimignano by sampling local specialties during a romantic candlelight dinner in the historic center or in a scenic winery outside of town. Enjoy artisan cheeses and charcuterie from the region, traditional Tuscan dishes such asribollita (Tuscan bread soup) and truffle pasta, and local wines paired with each course. Whether you choose to dine in town or in the countryside, be sure to catch the sunset over the rolling landscape at dusk, when the golden light creates a postcard-perfect view.