San Gimignano, Italy: The Manhattan of the Middle Ages

The Story of San Gimignano, Italy

We decided to add San Gimignano to our Tuscany itinerary, and we were so glad we did! It’s really easy to visit from cities like Siena and Florence, and it is one of the most famous villages in the region, thanks to its interesting medieval history.

We visited in September, which had the perfect climate for exploring: warm but not too hot, ideal for wandering the streets and discovering the medieval towers the village is famous for.

Did you know? Back in the Middle Ages, families in San Gimignano competed to build the tallest towers, trying to outdo one another. There used to be around 72 towers, which is why it’s known as the “Manhattan of the Middle Ages”.

Things to do in San Gimignano, Italy

1. Torre Grossa

We headed straight for Torre Grossa, which means ‘big tower’. It’s the icon of the town, standing at a mammoth 54 meters (the tallest tower in San Gimignano!). We found a spot to sit on the main square, Piazza del Duomo, and imagined what it was like to work in this watchtower, protecting against attacks from the valley below.  

Unlike many other towers we saw, Torre Grossa is open to visitors, so we could climb up the 218 steps to the top. Worth it for fantastic views over the town and the Tuscan rolling hills and vineyards! Get your tickets here.

As it’s the tallest of the towers, we also had a good view of the other towers below.

2. Cathedral Santa Maria Assunta 

Make sure to visit the Cathedral of Santa Maria Assunta, a stunning cathedral that dominates the Piazza del Duomo. Inside, we saw some of the most incredible frescoes and murals. 

In the same square, there’s the Palazzo del Podesta, which used to be the town’s mayor’s palace. The palazzo also has a tower named ‘Rosogna’(51 meters high); we didn’t climb this one, but if you have time, it’s worth a look!

3. Palazzo del Popolo, San Gimignano 

The Palazzo del Popolo is a stunning building that houses the local government office. Made from the typical San Gimignano stone, it has enormous medieval arched windows.

We only walked around the outside, but you can also pay to see the beautiful interior (with frescoes painted by some of Italy’s most famous artists!).

4. Eat Gelato

San Gimignano is home to one of the best gelatos we had on our entire trip: 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!). 

We visited in the middle of the day, so it was very busy; we waited in line for about 20 minutes, but it was worth it!

No time to read now?

No worries! Save on Pinterest to read it later.

Save to Pinterest

5. Piazza Della Cisterna

We stumbled across this really interesting triangular-shaped ‘square’ while wandering around San Gimignano. There’s a pretty well at its center, and its three edges are lined with beautiful ancient buildings.

Our favorite was the Torre del Diavolo (tower of the devil), which got its name after the owner returned from a trip to find the building taller than before. The only explanation he could find was that it was the devil’s work.

6. Cappella di Santa Fina 

Cappella di Santa Fina is a beautiful Renaissance chapel that honors a girl named Fina, who died at 15 in 1253. Locals say that when she died, people could see flowers growing from the board she slept on. And sick people who visited her remains said they were instantly cured. 

Part of her body is still enshrined in the chapel; it’s not a must-see, but it’s an interesting stop if you have time.

7. Go Wine Tasting 

Aside from gelato, Tuscany is known worldwide as the home of some of the greatest wines. As we looked down from the walls of San Gimignano, we saw endless vineyards spread out below us. We didn’t have time for a wine tour here, but if you do, make sure to try the local Vernaccia, one of the world’s oldest wines.

8. 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). We had some of the best pasta dishes here! 

9. Hike the Elsa Trail

Not far from San Gimignano, we discovered the beautiful Elsa Trail, which runs alongside a milky blue river. We did the 5 km round-trip hike and stopped for a dip in the stunning Diborrato Waterfall. It’s a perfect way to escape the heat if you’re visiting in summer.

We parked for free along the roadside near Spugna Bridge (a 20-minute drive from San Gimignano), but you can take bus 770 to the nearby village of Colle di Val d’Elsa.

Best Cafes and Restaurants

After a morning wandering around the town, we grabbed a takeaway at this fantastic pizzeria and ate it in the square. But there are also lots of beautiful restaurants with outdoor terraces where you can soak up the sun. Some other great spots to try are:

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

Where to Stay in San Gimignano

We stayed in Castiglion Fiorentino, about 1.5 hours away, because we wanted to stay in a villa with friends. However, if you want the authentic San Gimignano experience, stay for a night (or two) in the center. Once the day-trippers disappear, the town becomes super quiet, allowing you to really appreciate its charm and history. 

Our favorite hotels in San Gimignano 😴

View all

Agriturismo Il Segreto di Pietrafitta

San Gimignano

Fabio Apartments

San Gimignano

Podere Bellavista

San Gimignano

See available hotels in San Gimignano

Check available hotels

Check available hostels

How to Visit San Gimignano, Italy

San Gimignano, Italy, is perfectly located between Florence (1-hour drive) and Siena (1-hour drive), so it’s an ideal day trip. 

By Car

We rented a car to visit San Gimignano as part of our Tuscany road trip, which we definitely recommend for more flexibility. You’ll need to park outside the city walls, as most streets are pedestrianized.

• We parked at this location, just on the edge of the historic city center. Please note that it’s quite a steep walk into the village.
• If it’s full, there’s also this car park on the other side of town.

By Bus

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

However, there are plenty of organized tours leaving from Siena and Florence that 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, then take bus number 130. The train journey takes 25 minutes and costs approximately 4 EUR each way.

Best Time to Visit

We visited San Gimignano in late September, which was perfect. We had nice warm weather, but it wasn’t too hot, and it was less crowded than in July and August. If you are visiting in the summer months, try to visit early in the morning or late afternoon once the tour buses have left.

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