You’ll see the town at its lively best if you come on a Thursday or Saturday morning, when the interlocking Piazza della Cisterna and Piazza del Duomo fill with market stalls. Piazza della Cisterna is named for the well at its center, a fairly ingenious device that for centuries was a repository for rainwater channeled from rooftops—a reliable and safe source of water that could not be tampered with or contaminated by natural events occurring outside the city walls. For a refreshing break from the crowds, head up from the Duomo to the well-marked Rocca e Parco di Montestaffoli. Filling the shell of the town’s 14th-century fortress, this park provides greenery, quiet, and views over the town and countryside, all the better from the little tower in the far corner.

Anchoring the town at the top of Via San Giovanni are its two interlocking triangular piazze: Piazza della Cisterna, centered on a 1237 well, and Piazza del Duomo, flanked by the city’s main church and civic palace. It is easy to find them: From any direction, just keep walking uphill.

Civic Art

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Towers and medieval ambience aside, you’ll also discover that San Gimignano is full of frescoes and other art—in churches, public buildings, and even outdoors. In Piazza Pecori, reached through the archway to the left of the Collegiata’s facade, is a fresco of the “Annunciation,” possibly painted in 1482 by the Florentine Domenico Ghirlandaio. The door to the right of the tourist office leads into a courtyard of the Palazzo del Commune, where Taddeo di Bartolo’s 14th-century “Madonna and Child” is flanked by two works on the theme of justice by Sodoma. The simple 13th-century church of San Lorenzo in Ponte (Via Santo Stefano 8) features several frescoes depicting the life of St. Benedict (look for the scene where he almost gives into temptation and accepts a loaf of poisoned bread); entry to this church is included in the cumulative ticket that also includes Museo Civico & Torre Grossa. Galleria Continua (Via Del Castello 11, galleriacontinua.com, tel. 0577/943134, open daily 10am to 1pm and 2 to 7pm) introduces contemporary art to the town’s medieval ambiance, showcasing well-known and emerging artists in a former cinema, a tower, a cellar, and an old apartment.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.