7 Best Sights in San Gimignano, Tuscany

The town's main church is not officially a duomo (cathedral), because San Gimignano has no bishop. But behind the simple facade of the Romanesque Collegiata lies a treasure trove of fine frescoes, covering nearly every wall. Bartolo di Fredi's 14th-century fresco cycle of Old Testament scenes extends along one wall. Their distinctly medieval feel, with misshapen bodies, buckets of spurting blood, and lack of perspective, contrasts with the much more reserved scenes from the Life of Christ (attributed to 14th-century artist Lippo Memmi) painted on the opposite wall just 14 years later.

This family-run wine estate specializes in Vernaccia di San Gimignano, Tuscany's best-known white wine, and has a history dating to the 10th century (though its current owners took it over more recently, in 1977). A one-hour visit includes a tour and tasting of four to six wines. The property also includes three apartments inside a former convent.

The impressive civic museum occupies what was the "new" Palazzo del Popolo; the Torre Grossa is adjacent. Dante visited San Gimignano for only one day as a Guelph ambassador from Florence to ask the locals to join the Florentines in supporting the pope—just long enough to get the main council chamber named after him.

Upstairs, paintings by famous Renaissance artists Pinturicchio (Madonna Enthroned) and Benozzo Gozzoli (Madonna and Child), and two large tondi (circular paintings) by Filippino Lippi (circa 1457–1504) attest to the importance and wealth of San Gimignano.

Even with all the decoration in the Collegiata, the fine collection of religious articles in the church museum, across the pretty courtyard, is still worth a look. The highlight is a Madonna and Child by Bartolo di Fredi. Other pieces include several busts, wooden statues of Christ, the Virgin Mary, and the angel Gabriel, and several illuminated songbooks.

Across the piazza from the Collegiata is the "old" town hall built in 1239. Its tower was erected by the municipality in 1255 to settle the raging "my-tower-is-bigger-than-your-tower" contest—as you can see, a solution that just didn't last long. The palace is closed to visitors.

If you want to see more of that quintessential Tuscan landscape, walk up to the Rocca di Montestaffoli, which sits at the highest point in San Gimignano. Built after the Florentine conquest to keep an eye on the town, and dismantled a few centuries later, it's now a public garden.

Make a beeline for Benozzo Gozzoli's superlative 15th-century fresco cycle depicting scenes from the life of St. Augustine. The saint's work was essential to the early development of church doctrine. Benozzo's 17 scenes on the choir wall depict Augustine as a man who traveled and taught extensively in the 4th and 5th centuries. The 15th-century altarpiece by Piero del Pollaiolo (1443–96) depicts The Coronation of the Virgin and the various protectors of the city.