Dubbed “Medieval Manhattan”, San Gimignano turns heads with one of the most striking skylines in Tuscany. More than a dozen 14th-century towers soar above its UNESCO-listed historic center—just a fraction of the original 72 that once stood here—and visitors are drawn to the compact old town for its timeless atmosphere, unparalleled cuisine, and sweeping hilltop views over the surrounding Chianti countryside. Just beyond the city walls sit some of the most prestigious wineries in Tuscany, connected by scenic hiking, biking, and horseback riding routes.
A popular day trip destination from Florence, San Gimignano bursts with tourists in summer and on holiday weekends. A spring or fall weekday visit allows you to enjoy this medieval hill town in relative peace, plus you can take advantage of the cooler temperatures and see the surrounding hills blanketed in vineyards and olive groves. The town’s historic Ferie delle Messi, a medieval harvest festival, takes place in June, with period costumes, jousting, and entertainment.
Despite its outsized fame, San Gimignano is a tiny village that can be crossed on foot in minutes. Most of the old town is closed to traffic, so pedestrians have the lanes to themselves to wander and explore. Because there is no train station, day-trippers must arrive from Florence by bus or car; the historic center is ringed with small parking areas that are a short walk from the thoroughfare and square.
In addition to its 14 landmark towers, San Gimignano is home to another iconic attraction: Gelateria Dondoli, where celebrity gelataio Sergio Dondoli holds court among his tubs of gourmet gelato, considered some of the finest in Italy. Try his trademark flavors like crema di Santa Fina flavored with certified San Gimignano saffron and pine nuts, vernaccia sorbet featuring the area’s famous white wine, and Champelmo, a mix of pink grapefruit and bubbly.
