15 Best Things to Do in San Gimignano (Medieval Tuscany Guide)

ByGabriella

San Gimignano is one of Tuscany's most iconic medieval villages - famous for its towers, Vernaccia wine, and saffron gelato. Here is everything I love about it and how to spend your time there.

For more Tuscany inspiration, read my Florence travel guide and my guide to Siena.

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San Gimignano was one of those discoveries that completely blindsided me. I was driving through Tuscany on my way somewhere else - Florence to Siena, I think - when I spotted the towers from the road and made an impulsive turn. I have been going back ever since.

The medieval towers rising above the Tuscan countryside are like nothing else in Italy: dramatic, slightly absurd, completely beautiful. The village has been called Medieval Manhattan and once you see it, you understand why.

But what I love most about San Gimignano is that beyond the famous skyline it rewards people who slow down - there are remarkable wineries nearby, genuinely excellent food, and a pace of life that feels untouched by the tourism that crowds its main piazza.

How to Get to San Gimignano

From Florence

Train + Bus (best option):

  • Train to Poggibonsi (1 hour)
  • Bus to San Gimignano (20 minutes)
    Total: ~1.5 hours, €10-€15

Drive (best experience):

  • ~1 hour 15 minutes through the Tuscan countryside
  • Park outside the historic center (no cars allowed inside)

From Siena

Bus: ~1 hour 15 minutes (direct)
Drive: ~45 minutes

From Pisa

  • Train to Poggibonsi + bus
    Total: ~2-2.5 hours


The Best Things to Do in San Gimignano

Visit Guardastelle Vineyard

I genuinely consider this one of the best experiences I have had in Tuscany - and I have had many. Guardastelle is a small family vineyard just outside San Gimignano producing DOCG wines and olive oil with an almost obsessive attention to quality.

The lunch they prepare is extraordinary: olives, ribollita, bruschetta drenched in their own oil, a spread of meats and cheeses, dessert wine with biscotti. Our host Barbara's enthusiasm for the wine and the land was completely infectious. This is the kind of place that makes you want to cancel your onward plans and stay another day. Reserve in advance - it fills up.

Tour the Historic Center of San Gimignano

Walking into San Gimignano's historic center for the first time feels slightly unreal - like a medieval film set that happens to also be a living town. The towers dominate the skyline and the stone lanes are full of artisan shops, ceramic workshops, and the smell of saffron from the local gelato.

Do not miss the Galleria di Arte Moderna e Contemporanea Raffaele De Grada, which has a surprisingly strong collection of contemporary art that provides an interesting contrast to all the medieval architecture around it.

Piazza della Cisterna

Every visit to San Gimignano eventually leads to Piazza della Cisterna, and every time it stops me in my tracks. The 13th-century triangular piazza is anchored by a well dating back to 1287 - you can still see the grooves worn into the travertine rim by centuries of rope pulling water.

The towers of the Ardinghelli family and the famous Torre del Diavolo frame the square. I like to arrive early in the morning before the crowds and just sit with a coffee and let the place sink in.

Visit Podere La Marronaia Biodynamic Winery

This family-run organic and biodynamic winery just outside San Gimignano is one of my personal favorites in all of Tuscany. Pietro and Corrado host wine tastings, truffle hunts, cooking classes, and farm-to-table meals that are as genuine as it gets. I stayed here overnight and it remains one of the most memorable experiences of any Tuscany trip - waking up to views of the rolling hills and sitting down to a meal made almost entirely from the farm. The wines are excellent. Book ahead.

Fattoria Il Piano Winery

Going to Fattoria Il Piano felt like stumbling onto a well-kept secret. David, the man who runs it, talks about wine the way a good teacher talks about their subject - with stories instead of data, with passion instead of performance.

The tour takes you through the vineyards and into the cellar, and the tasting at the end is generous and informal. Fair warning: you will almost certainly leave with a heavier trunk and lighter pockets. Go by car - it is a steep approach.

Climb San Gimignano Bell Tower

Torre Grossa is the tallest of the surviving towers and the only one open to the public. The climb is steep and a little breathless but the view from the top - towers, terracotta roofs, rolling vineyards, endless Tuscan hills - is worth every step. Open 10am to 7:30pm. Get there early to avoid the worst of the queues.

Torre Grossa (or Torre del palazzo del Podesta)

A slightly easier climb than Torre Grossa and with a different perspective on the town - looking across at the other towers from the bell tower gives you a sense of just how dramatic this skyline must have appeared in the Middle Ages when all 72 were standing.

Where Is San Gimignano?

San Gimignano is a small medieval hill town in Tuscany, central Italy, known for its iconic stone towers and panoramic countryside views.

You'll find it:

  • About 50 km southwest of Florence
  • About 40 km northwest of Siena

It sits on a hill surrounded by vineyards and olive groves, right in the heart of the Tuscan countryside.

Map of San Gimignano, Italy

San Gimignano Travel Tips

  • Visit in spring or fall. May, June, and September offer good weather with manageable crowds. Summer is beautiful but extremely busy and the narrow lanes fill up quickly with tour groups.
  • Wear proper shoes. The streets are cobblestone and uneven - comfortable walking shoes are essential.
  • Park outside the walls. Cars are not permitted in the historic center. Park in the designated lots outside the city walls and walk in - it takes about five minutes.
  • Book accommodation early. If you plan to stay overnight (which I recommend), book well in advance especially for spring and summer.
  • Carry cash. Many smaller shops, wineries, and food stalls prefer cash. ATMs are available in town but can have lines.
  • Fill up your water bottle at public fountains. The water is good and it saves money and plastic.
  • Dress modestly for churches. Shoulders and knees covered when entering the Collegiata or any church.
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When is the Best Time to Visit San Gimignano?

During the shoulder seasons of spring and fall, I believe, is the ideal time to visit San Gimignano. When opposed to the busiest summer months, these times of year are my favorites because of the often great weather and lower crowds.

How Long Do You Need in San Gimignano?

I've found that in order to really enjoy San Gimignano's beauty, you need plan to stay there for at least one whole day. I will have plenty time to stroll around the charming streets, take in the stunning medieval towers, and take in the rich historical aura of the town.

Day Trips From San Gimignano

San Gimignano sits perfectly between Florence and Siena, making it an ideal base for exploring central Tuscany. My favorite day trips from here:

  • Siena - one of my favorite cities in all of Italy, deeply romantic and perfectly walkable.
  • Florence - the Renaissance capital of the world, about 50 minutes by car.
  • Volterra - Etruscan heritage, medieval architecture, and alabaster workshops; far fewer tourists than San Gimignano.
  • Greve in Chianti - the heart of Chianti wine country with small wineries and excellent food.
  • Pisa - yes, the Leaning Tower, but also a genuinely interesting city that most visitors rush through too quickly.
  • Lucca - beautiful walled city with Renaissance walls you can walk and cycle along.
  • Montepulciano - hilltop wine town with stunning views and some of the best Vino Nobile in Italy.

Where to Stay in San Gimignano

Hotel L'Antico Pozzo: Right in the heart of San Gimignano, this intimate hotel has genuine charm - stone walls, comfortable rooms, and owners who treat you like a friend rather than a guest number. The third-floor rooms get good light. I have stayed here and would go back without hesitation.

Podere La Marronaia  -  Luxury / Agriturismo: A biodynamic farm stay just outside San Gimignano with stunning countryside views, exceptional food, and the kind of genuine Tuscan hospitality that is increasingly hard to find. Best for travelers who want to slow down and experience rural Tuscany properly.

Where to Eat in San Gimignano

Here's a list of 9 of our favorite places to eat in and around San Gimignano. Check them out and also be sure to look up some restaurants on your own by clicking here.

FAQs About San Gimignano

Is San Gimignano worth visiting?

Absolutely - it is one of the best-preserved medieval towns in Europe and the towers alone are worth the trip. Go early in the morning or in the late afternoon to avoid the worst of the day-tripper crowds.

How far is San Gimignano from Florence?

About 50 kilometers - less than an hour by car. It makes an easy and very rewarding day trip from Florence, though I recommend staying at least one night if you can.

What is San Gimignano famous for?

Its medieval towers (14 of the original 72 still stand), Vernaccia di San Gimignano white wine (one of Italy's oldest DOCG wines), saffron gelato, and its remarkably well-preserved historic center - a UNESCO World Heritage Site since 1990.

What movies were filmed in San Gimignano?

Notable films include The English Patient (1996), Tea with Mussolini (1999), A Room with a View (1985), Under the Tuscan Sun (2003), and the TV series The Medici: Masters of Florence (2016).

How long do you need in San Gimignano?

One full day is enough to see the main sights. Two days lets you add a winery visit and explore the surrounding countryside at a proper pace. If you plan to use it as a base for Tuscany day trips, three nights works well.

How far is San Gimignano from Florence?

In my opinion, San Gimignano is a great day trip location because of its so close to Florence. In other words, the average driving time it took us from San Gimignano to Florence was less than 50 minutes. Therefore, because of this short distance, visitors spending a vacation in Florence could very easily get to experience the medieval marvel that is San Gimignano and then return to Florence that very same day.

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