San Gimignano, about 50 kilometers southwest of Florence, owes its almost pristine medieval appearance. The town attracted important later Renaissance artists such as Domenico Ghirlandaio, Benozzo Gozzoli, and Benedetto da Maiano, whose works you can witness in the town’s churches. The structures remained almost unaltered until recent restorations promoted by UNESCO set about preserving them. S
The town's major attractions for tourists are the 13 towers that remain from the original 70 and give San Gimignano its distinctive skyline (it is known as the medieval Manhattan).
Here is a list of the top ten attractions and activities!
1. Visit the Old Town
There is no doubt that the main appeal of San Gimignano is its Old Town, the Centro Storico, bristling with square towers that were both fortified homes and status symbols for the rival families that built them.
At the heart of this old center is little Piazza della Cisterna, the town's triangular main square, where you'll find a cluster of these: the stump of a tower on Casa Razzi, the remains of another on Palazzo Tortoli, the tall Torre del Diavolo (Devil's tower) on the Palazzo dei Cortesi, and the two Torri Ardinghelli on the west side.
The piazza's patterned brick pavement leads to Via del Castello, where you'll find more noble homes and towers. Overlooking Piazza del Duomo are the two Torri Salvucci, said to have been built for the purpose of bypassing the Communal Statutes of 1255 that limited towers to the height of the Podestà Tower. To show their superiority (and to annoy their rivals, the equally powerful Ardinghelli family) the Salvuccis supposedly built two whose combined height was taller than the Podestà.
2. Admire the Church of Santa Maria Assunta
The Romanesque church of Santa Maria Assunta was built originally in the 12th century, but in 1457, it was enlarged by Giuliano da Maiano, who added a transept and side chapels. The starkly plain facade faces the misleadingly named Piazza del Duomo; this is not a cathedral and there has never been one in San Gimignano. Inside the church are several outstanding fresco cycles.
On the entrance wall is a 15th-century fresco by Benozzo Gozzoli and two wooden statues of the Annunciation from the same period, by Iácopo della Quercia. In the right-hand aisle is a monumental 14th-century cycle by Barna da Siena, with three bands of New Testament scenes. Its counterpart in the left-hand aisle is a series of highly restored Old Testament scenes by Bartolo di Fredi.
The Renaissance Cappella di Santa Fina, by Giuliano and Benedetto da Maiano (1468) honors San Gimignano's patron saint, much revered for miracles. The altar, also by Benedetto da Maiano, holds a tabernacle with relief decoration and the remains of St. Fina. In the arcades on either side of the altar are frescoes by Domenico Ghirlandaio (1475) depicting the life and death of St. Fina.
3. See the Rocca
Built against the town walls on the highest point of the hill is the rocca (castle), erected by the Florentines in 1353 but demolished in 1555 on the orders of Cosimo I.
Only a tower and fragments of the walls survive, and from the top are magnificent views of the town and surrounding countryside.
Each year on the third weekend in June, a tournament, La Giostra dei Bastoni (a joust), is held here as part of the Ferie delle Messi, a medieval festival.
4. Explore the Rocca di Montestaffoli
Walk up the hill from Piazza delle Erbe to La Rocca di Montestaffoli, the ruins of the 14th century fortress above the town. Lovely olive groves provide a bit of shade from the sun and a great place to enjoy salami on a baguette while taking in the views of the rolling Tuscan hills and the towers rising from the town center. Roving musicians like the harpist pluck out classical tunes while artists set up their easels and paint.
During the summer, there is an outdoor cinema and you can learn more about Tuscany’s best known white wines at the Museo del Vino (Wine Museum) after having taken a walk through the vineyards or having done a wine tasting in a winery.
5. Climb the Torre Grossa
Torre Grossa, the tallest tower at 54 meters (177 feet) in height and dating from 1298, is the only tower open to the public.
Climb to the top for views over the picturesque countryside.
6. Drink Vernaccia di San Gimignano
When you think of Tuscany, you probably think of Chianti. But the vineyards around San Gimignano produce the white wine grape Vernaccia, so famous it was even mentioned in Dante’s Inferno.
Vernaccia di San Gimignano is a crisp white wine with citrus fruit flavors. Enotecas are disseminated through the medieval streets and you can even get a plastic glass to go, which you can take to one of the many panorama viewpoints to enjoy while gazing over the stone Tuscan farmhouses and rolling green hills.
7. Cool off with a gelato
The world-famous Gelateria di Piazza is right in the center of Piazza della Cisterna and has a variety of creative flavors like saffron or pink grapefruit with sparkling wine, aside from the traditional one.
You’ll easily recognize it because there is always a line out the door. This is the most popular way for locals to cool off on a hot summer day.
8. Do some window shopping
Shops and boutiques built right into the stone walls line the alleys of San Gimignano.
You’ll find specialty food, wine, leather, and ceramic shops. Typical fine Italian leather can be found for much less than in nearby Volterra or Florence. Window shopping might tempt you to make a purchase and come home with a new leather bag.
9. Buy and taste wild boar salami
Gourmet shops all throughout San Gimignano sell local wild boar sausage. It even comes with red wine, truffles, fennel, or pine seeds and is thinly sliced and served on a crusty baguette drizzled with olive oil. Grab a salami baguette and a bottle of Vernaccia and head up to La Rocca for a picnic lunch.
10. Have dinner overlooking the town
There’s hardly a more romantic spot to sip on wine and have dinner than the Agriturismo Taverna di Bibbiano, which looks directly at San Gimignano with outdoor tables on the edge of a hillside planted with a lavender field.
The menu changes regularly based upon what ingredients are in season as everything comes fresh from the farm. You can for example have a pear salad drizzled with balsamic glaze or olive oil, pici pasta and Tuscan meatballs in a Chianti sauce accompanied by grilled, stuffed tomatoes. You can also taste and drink a bottle of Chianti as you watch the sun slowly die behind the hills.