San Gimignano, Italy: The Manhattan of the Middle Ages

The Story of San Gimignano, Italy

San Gimignano, Italy, has stood on this beautiful hilltop for over 800 years, dating back to the Middle Ages. Back in those times, families competed to build the tallest towers, all trying to outdo each other. The higher you could build, the more you elevated your status as the wealthiest family in the town. 

In the Middle Ages, there were around 72 towers. However, these days, there aren’t as many left (there’s some debate about how many are still standing. We think about 14!).

San Gimignano has also been awarded UNESCO world heritage status to protect the ancient buildings and teach about their immense history. This is just one of the reasons why San Gimignano is one of the most famous villages in Tuscany! Plus, it’s only 25 miles north of Siena, so it’s the perfect day trip.

Things to do in San Gimignano, Italy

San Gimignano may be small, but that doesn’t mean there aren’t lots of things to do. Just wandering the beautiful meandering streets is an activity, exploring hidden corners and discovering beautiful churches and houses.

Because of its popularity, San Gimignano can get very busy. However, there’s always a secluded spot to be found where you can take photos and absorb the history of the medieval town. 

1. Torre Grossa

Torre Grossa (meaning ‘big tower’) stands at 54 meters and is the tallest tower in San Gimignano. Sitting on the main square of Piazza del Duomo, this tower was used as a watchtower to protect against attacks from the valley below.  

Unlike many other towers, Torre Grossa is open to visitors, allowing you to climb up the 218 steps to the top for fantastic views over the town and the surrounding rolling hills and vineyards. Plus, as it’s the tallest of the towers, you’ll have a good view of the other towers below.

Cathedral Santa Maria Assunta 

Make sure also to take a look at the Cathedral Santa Maria Assunta, a stunning cathedral that dominates the Piazza del Duomo. Inside you’ll find incredible frescoes and murals that depict biblical scenes. 

Entry fee: 4 EUR or 6 EUR if you want to go to the adjoining sacred art museum. 

2. Palazzo del Popolo, San Gimignano 

The Palazzo del Popolo (meaning ‘people’s palace’) is a stunning building that houses the local government office. Made from the typical San Gimignano stone, it has enormous medieval arched windows and a beautiful interior. It’s mainly known for the extraordinary frescoes you can see inside, painted by some of the most famous Italian artists of all time. 

3. Eat Gelato

There is no activity more important in Italy than eating gelato! San Gimignano is the best place to do it, as it’s home to the fantastic Sergio Dondoli Gelateria. Sergio Dondoli was the first to put white wine in his ice cream (genius!) and prides himself on his unusual flavors, serving everything from dark chocolate and chili pepper gelato to saffron and pine nuts (trust us, it works!). 

It’s no surprise that it’s been named ‘The World’s Best Gelato’, drawing travelers and celebrities from all over the globe. Because of this, the gelateria is always very popular so you may have to queue. However, it’s well worth it!

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4. Piazza Della Cisterna

Piazza Della Cisterna is a pretty square named after a cistern (well) at its center. Unusually, its shape is triangular rather than square, with beautiful, ancient buildings surrounding its three edges.

One of those buildings is the Torre del Diavolo (tower of the devil) which got its name after the owner returned to San Gimignano to find the building taller than it was before. The only explanation he could find for the magic was that it was the devil’s work.

5. Cappella di Santa Fina 

Cappella di Santa Fina is a beautiful renaissance chapel with a fascinating history. It was named after Fina, a young girl who died at 15 in 1253. She had a terminal illness, but her faith prevented her from feeling pain (she even chose to sleep on a wooden board rather than a bed). When Fina died, the story says that local people could see flowers growing from the board. What’s more, when sick people visited her remains, they were instantly cured. 

Because of these miracles, Fina is commemorated in the town, and part of her body is even enshrined in the chapel. Visit the chapel, learn more about Fina, and see the beautiful designs and sculptures inside.

6. Go Wine Tasting 

Aside from gelato, Tuscany is known worldwide as the home of some of the greatest wines. As you look down from the walls of San Gimignano, you’ll see acres and acres of gorgeous vineyards spread out before you.

One of the most famous areas in Tuscany is the Chianti wine region which is well worth a visit. You can also try Vernaccia white wine in the area, which is one of the oldest wines in the world, much like San Gimignano itself! 

7. Day Trip to Siena

If you’re basing yourself near San Gimignano on your road trip in Tuscany, make sure to carve out a day to visit the nearby city of Siena (only an hour’s drive away). The atmospheric city is home to narrow, steep streets, ancient squares, churches, and some of the best pasta dishes going! 

8. Hike the Elsa Trail

Not far from San Gimignano, discover the beautiful Elsa Trail, a meandering path in nature that follows along a milky blue river. Follow the path for a few kilometers (5 km round trip) and discover the stunning Diborrato Waterfall, a 15-meter-high waterfall. This is the perfect place to stop and enjoy a refreshing swim in the pools below, enjoying the cooling spray from the mighty waterfall.

There is plenty of free parking nearby (a 20-minute drive from San Gimignano) or take the bus (770) to the nearby village of Colle di Val d’Elsa.

Best Cafes and Restaurants

Delicious food is everywhere in San Gimignano, whether it’s the unique flavors of ‘The World’s Best Gelato’, the creamy taste of local pecorino cheese, or a smooth glass of Chianti wine. After a morning wandering around the town, book lunch at one of the lovely restaurants in the town, each with a beautiful outdoor terrace where you can sit and enjoy the flavors of Italy in the sun. Some great places to try are:

Alternatively, for an amazing food experience in San Gimignano, book a Tuscan cooking class!

Where to Stay in San Gimignano

If you want the authentic experience of San Gimignano, stay for a night (or two). Once the day-trippers disappear, the town becomes super quiet, allowing you to really appreciate its charm and history. 

Hotels in San Gimignano 😴

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Agriturismo Il Segreto di Pietrafitta

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Fabio Apartments

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Podere Bellavista

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Stay in one of the apartments or hotels in San Gimignano itself, or choose a charming agriturismo outside of the city parameters, deep in the Tuscan countryside. Either option is perfect as a stopover on your road trip through Tuscany.

How to Visit San Gimignano, Italy

San Gimignano, Italy, is perfectly located between Florence (1-hour drive) and Siena (1-hour drive), making it great to visit on a day trip. 

By Car

Rent a car in Italy and add San Gimignano to your itinerary for the real Tuscany road trip experience. It means you have the flexibility to drive through the Tuscan countryside, making stops as you go. When you get to San Gimignano, there is parking outside the city walls. Please note that it’s quite a steep walk into the village.

By Bus

There are no direct buses to San Gimignano; you’ll need to take a bus to the nearby town of Poggibonsi and then jump on the local bus 130.

However, there are plenty of organized tours leaving from Siena and Florence, which include your return journey (and sometimes a tour guide).

By Train

There is no train station in San Gimignano. However, you can take the train from Siena to Poggibonsi and then get on bus number 130. The train journey takes 25 minutes and costs approximately 4 EUR each way.

Best Time to Visit

San Gimignano is extremely popular all year round. However, the busiest times are always the summer months (June – August), when vacationers come from all around Italy to visit. This means it can get crowded, especially when the tour buses visit at peak times of the day. Because of this, we recommend visiting outside of those hours, either early in the morning or late afternoon/evening when the tour groups have left.

To see it at its most tranquil, stay a night in San Gimignano and enjoy the beautiful views at dusk or dawn.