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Things to do in San Gimignano

Itineraries for Your Trip to San Gimignano

San Gimignano locals share their perfect days.
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3 Days in San Gimignano for Foodies

Curated by Rebecca Winkean Italophile and travel enthusiast who’s lived in and written about Italy for more than two decades.

Located on a scenic hilltop within striking distance of three top Tuscan culinary destinations—Chianti, Val d’Orcia, and the Crete Senesi—San Gimignano is a formidable foodie hub. Within a short drive, you can feast on black truffles, pecorino sheep cheese, artisan charcuterie made from heirloom cinta senese pork, and some of Italy’s flagship red wines. Plus, the old town is crowded with enough traditional Tuscan trattorias to keep you fed for weeks.

I didn’t have high expectations for dining on my first trip to San Gimignano. Instead of tourist traps, I found excellent and authentic culinary experiences inside and outside the city walls. Here’s how to experience some of Tuscany’s best food and wine over three days in San Gimignano.

Torrid summer days make gelato a must in San Gimignano; stop at the award-winning Gelateria Dondoli for a refreshing scoop.

If you only have time for one thing, make it an area winery for a tasting.

Day 1

Set off from the UNESCO-listed medieval center and famous towers of San Gimignano for an excursion into the wine country outside of town. Stroll through the vineyards and taste a variety of local red and white wines, plus relax with an authentic Tuscan lunch overlooking the hills.

Go hands-on this afternoon for a deep dive into traditional Tuscan fare with a cooking class at a farmhouse on the San Gimignano outskirts. Learn the secrets to making pasta, sauces, and main courses from your local host and instructor. Enjoy a family-style dinner featuring the dishes you made to cap off the experience.

Day 2

Enjoy an introduction into the world of Tuscany’s prized black truffle with a morning truffle hunt, accompanied by a local forager and crew of trained dogs. Set off through the Tuscan woods to see how dogs sniff out the truffles under the forest floor. Then, feast on a truffle-themed lunch.

The hills surrounding San Gimignano are known for red wine, black truffles, and golden olive oil. This afternoon, visit a family-run olive farm to tour and taste their traditional extra-virgin olive oil. Learn about the history of local olive oil production and discover how to identify quality olive oil.

Day 3

Drive about an hour south to Siena for a food tour through the UNESCO-listed old town. Admire the main Piazza del Campo square, a Gothic cathedral, Mangia Tower (Torre del Mangia), and other landmarks while sampling sweet and savory specialties.

Afterward, continue further south to the Val d’Orcia, where family farms have raised sheep and heirloom Cinta Senese pigs for generations. Connect with a local family to learn about their artisan production and taste pecorino cheese and charcuterie.

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