In a nutshell
- San Gimignano is one of the most beautiful towns in Tuscany — and totally doable as a half-day stop.
- You don’t need more than 2 to 3 hours to see San Gimignano’s highlights.
- There are currently 14 towers in San Gimignano — in the Middle Ages there were as many as 72. That’s where the nickname Manhattan of the Middle Ages comes from.
- Most visitors are day-trippers. Arrive in the late afternoon and the alleyways will be far less crowded — plus the sunsets are seriously stunning.
- Don’t leave without tasting the local wine: Vernaccia di San Gimignano is the region’s famous white, and it’s absolutely worth a glass (or two).
Our Top 8 Things to Do in San Gimignano
San Gimignano is Tuscany at its finest. Medieval alleyways, towers, and breathtaking views — if you’re doing a road trip through Tuscany, you absolutely have to stop here.
These are the must-see highlights in San Gimignano:
Piazza del Duomo
In Italy, even a village of 7,000 people like San Gimignano has a cathedral and a cathedral square.
It sits right in the heart of the little town and is simply pure Middle Ages.
Alongside the cathedral, you’ll find the town hall and several of the family towers here, including the Torre Grossa, the tallest tower in San Gimignano.
Every now and then, a puppet performer shows up on the cathedral square, adding even more to the medieval atmosphere.
Torre Grossa
San Gimignano has 14 towers, all dating from the 13th and 14th centuries.
At one point there were as many as 72 — hard to imagine in such a small medieval town. That’s where the nickname Manhattan of the Middle Ages comes from.
The Torre Grossa is the tallest tower at 54 meters.
It stands right next to the town hall, and your ticket for the tower includes entry to the Pinacoteca in the town hall and the cathedral.
The climb is quite an adventure: you’ll tackle around 220 steps before squeezing through a narrow hatch onto the observation platform.
The panorama is absolutely stunning — you can see not only all of San Gimignano but the entire surrounding landscape as well.
Piazza della Cisterna
Right next to the Piazza del Duomo is the Piazza della Cisterna. The triangular square has a cistern in the middle that people drew water from during the Middle Ages.
To this day you can still see the grooves worn by the thick ropes that were used to lower buckets into the well.
The square has several cafés and restaurants, and the steps leading up to the fountain are also a popular spot to sit.
Right on the square stands a tower that looks a little different from the others in San Gimignano: legend has it that the devil himself built it — hence the name Torre del Diavolo.
Gelateria Dondoli
The Gelateria Dondoli on the Piazza della Cisterna makes outstanding gelato — even by Italian standards. It’s widely considered one of the best ice cream shops in the world.
With its innovative flavors, it has actually won multiple world championship titles: raspberry with rosemary, ricotta with blueberry, or saffron cream.
Plenty of tourists know about this place, and the line outside is correspondingly long.
But the wait is totally worth it — the gelato tastes simply divine!
Viewpoint Via degli Innocenti
Running parallel to the Piazza della Cisterna is the alley Via degli Innocenti, which offers a truly wonderful vista over the vineyards surrounding San Gimignano.
You can reach it by taking the alley downhill to the left of the Gelateria Dondoli and then turning left.
It’s most beautiful here in the late afternoon or at sunset!
Torre e Casa Campatelli
The Casa Campatelli is a manor house with its own family tower, bequeathed by the last heir of the Campatelli family to the Italian National Trust.
You can stroll through the rooms and admire the original furnishings and personal belongings of the wealthy Campatelli family from the 19th century.
The tour begins with a video projection about the history of San Gimignano. Absolutely recommended!
Get tickets for the Casa Campatelli
Rocca di Montestaffoli
Next to the cathedral, a narrow alley leads up the hill to the castle ruins of Montestaffoli.
There’s also a small playground and a lawn with park benches here.
Not much of the castle itself remains, apart from the fortress walls and a single tower. You can climb to the top, and admission is free.
From up there you get another lovely view of San Gimignano and the surrounding vineyards.
Wine Experience La Rocca
Right next to the entrance to the castle ruins is an old farmhouse where wine tastings are held.
Here you can sample several varieties of Vernaccia di San Gimignano, the region’s famous white and red wines.
A local sommelier will walk you through the distinctive features of the vineyards around San Gimignano, and you can seriously expand your wine knowledge while soaking up views of Tuscany.
The Best Time to Visit San Gimignano
San Gimignano is small, the alleyways are narrow, and the tourists are many.
In peak season it can get very crowded very quickly, which puts a damper on sightseeing. But if you’re in Tuscany around Easter or during the summer anyway, we recommend heading to San Gimignano in the late afternoon.
The town is small to begin with, and you won’t need more than a few hours to see it.
Most tourists arrive in the morning and at midday and clear out by late afternoon.
Plus, the sunsets in San Gimignano are truly one of a kind — so it’s definitely worth being there in the second half of the day.
In the evening it gets even quieter, and the towers and alleyways are beautifully lit up. San Gimignano feels like a whole different place after dark!
Our Hotel Recommendations in San Gimignano
Staying overnight in San Gimignano is incredibly romantic — in the evenings the medieval alleyways are nearly deserted and perfect for a leisurely stroll.
There aren’t many hotels, but the ones that exist have truly beautiful rooms. Here are the places to stay we recommend in San Gimignano:
How to Get to San Gimignano
San Gimignano has no train station, so you can only reach the town on four wheels.
From Florence it’s about an hour’s drive, and from Siena about 30 minutes.
Right outside the town gates there are several parking lots where you can leave your car. You can’t miss them — they’re well signposted.
Once you walk through the town gates, it’s pedestrians only.
That said, you don’t necessarily need your own car — there are also tours you can book from Florence or Siena:
Bus tour from Florence: Full-day tour with stops in San Gimignano, Monteriggioni, and Siena, including wine tasting.
Bus tour from Siena: Sunset tour to Montalcino and San Gimignano, with dinner at a winery.
