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Things to do in San Gimignano

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3 Days in San Gimignano for Families

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

The glory of historic art and architecture is often lost on young travelers, but soaring towers are a hit at all ages—and San Gimignano is home to more than a dozen show-stoppers. The city’s Torre Grossa was one of the first medieval towers my sons scaled, and, decades later, it is still one of their favorite sky-high perches in Italy.

In addition to its unforgettable skyline, San Gimignano also offers a largely traffic-free old town, endless options for kid-friendly dining, and easy access to the hill towns of Chianti, the Val d’Orcia, and the Crete Senesi. If you time your touring to skirt the midday crowds, this historic gem is an excellent base for a family getaway to Tuscany. Here are my tips for making the most out of three days in and around San Gimignano for kids and grown-ups alike.

If you only have time for one thing, climb the 218 steps to reach the panoramic top of Torre Grossa.

The midday summer temperatures soar in San Gimignano, so schedule tours and activities for the cooler morning and late afternoon.

Day 1

You may know that San Gimignano is a UNESCO World Heritage Site, but your kids will be more impressed by the 14 medieval towers piercing the sky far above the rooftops. Take a stroll through town, stopping to climb to the top of Torre Grossa, explore the ruins of the 16th-century fortress, and pop in the shops along the pedestrian lanes of the historic center.

Take a break from the crowds in San Gimignano with an escape to the Chianti countryside this afternoon. Enjoy a scenic drive through the postcard-perfect hills, stopping to explore the tiny villages of Radda, Castellina, and Greve in Chianti. Active families with older kids can opt to hike, join an e-bike excursion, or set off on horseback with a guide.

Day 2

Take a family trip to Siena this morning, less than an hour south of San Gimignano. Famous for the chaotic Palio horse race that takes place in the Piazza del Campo square each summer, Siena is an ideal destination for a treasure hunt. Each of its 17 contrade (districts) that compete in the Palio are represented by animals and other symbols, which decorate historic facades and fountains around the old town center.

Tuscany is famous for its rustic cuisine, so take a break from touring and enjoy some hands-on fun with a family-friendly pasta-making class. Join your chef instructor at a countryside winery to roll and shape fresh pasta made from scratch. The grown-ups can take a quick tour of the cellar and sample the wines over dinner featuring the pasta you’ve prepared together.

Day 3

Get ready for a woodland adventure this morning with a forager guide and squad of expert dogs. Set off on a truffle hunt and learn how the trained pups sniff out rare black truffles for a yummy treat (not the truffles!), then celebrate your precious haul over a farm lunch with your forager hosts.

Otherwise, head to the UNESCO-listed hills of the Val d’Orcia to visit a sheep or heirloom Cinta Senese pig farm. Meet the animals and learn how they have been raised in these hills for generations, then try farm-fresh pecorino cheese and charcuterie or relax over a rustic farm-to-table lunch.

Spend your final evening in San Gimignano enjoying the streets as they quiet down after the bus-tour crowds have left. Take a stroll through the picturesque old town for a final gelato at the foot of its iconic towers.

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