How to Spend Two Days in San Gimignano: A Tuscan Dream
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San Gimignano is a popular day-trip destination from Florence, but if you can, you should stay a couple of nights instead.
This small Tuscan town is known for its unique medieval skyline. With its 14 towers it is an impressive sight, and I can only imagine what it looked like when all the original 72 towers were still standing. No wonder why it’s nicknamed Medieval Manhattan!
Unfortunately, San Gimignano also has a reputation of being over-crowded and too touristy. And there is no doubt there are a lot of people visiting, especially in high season. But that’s also why you should spend two days in San Gimignano instead of visiting on a day trip. Read on to find out what to do to beat the crowds and get the best of the town and the surrounding area.
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Introduction to San Gimignano
San Gimignano is a small hilltop town in the heart of Tuscany, about 56 km south of Florence, surrounded by vineyards, olive groves and rolling hills. It is located in the province of Siena, overlooking the beautiful Val d’Elsa countryside.
During the Middle Ages, San Gimignano was an important stop along the Via Francigena, the ancient pilgrimage route connecting northern Europe with Rome. The town became independent in 1199 and grew wealthy through trade. Rich and powerful families built tall stone towers to show off their wealth and status, creating the famous skyline we still see today.
UNESCO and Today
In 1990, the historic centre of San Gimignano was added to the UNESCO World Heritage List. This is not only because of its towers, but also because the town has preserved much of its original medieval layout, architecture and remarkable works of art.
Today, San Gimignano is one of Tuscany’s most popular destinations, attracting visitors from all over the world. Despite the crowds, it is still a wonderful place to explore, with narrow cobblestone streets, medieval squares, small shops and beautiful views of the surrounding countryside.
Find my itinerary for one week in Cinque Terre and Tuscany here.
How many days do you need in San Gimignano
As mentioned above, San Gimignano is a popular day-trip destination from Florence. So popular that the narrow medieval streets get packed with people who all try to see as much as they can within a limited timeframe.
Instead, I recommend staying overnight. One night is better than none, but if you can, stay two nights. This will give you two evenings to enjoy the old town with fewer crowds as well as one full day to explore the surrounding countryside.
You can also stay longer and use San Gimignano as a base for exploring this part of Tuscany.
The Perfect 2-Day San Gimignano Itinerary
I spent 2 nights here, celebrating my 40th birthday, in mid-October 2025, and it was simply perfect. This itinerary isn’t exactly how we did it, but how would recommend my best friend to spend two days in San Gimignano.
Get my 9 best tips for visiting Cinque Terre here.
Day 1: Arrival and Sunset from Torre Grossa
The easiest way to get to San Gimignano is by car, and it’s located approx. 1,5 hours’ drive from both Florence and Pisa International Airports. We came from Cinque Terre with a small detour to Volterra, and the drive from La Spezia is just under 2,5 hours if you go directly.
After checking in to your accommodation, it’s time to start exploring. And what’s better than getting an eagle’s eye view first thing?
At 54 metres, Torre Grossa is the tallest tower still standing and also the only one you can climb. It dates back to 1310 and is an important historic symbol of the town and Tuscany as a region. If you can, try to time your visit to sunset. We made it just in time and the view was nothing but mesmerising!
Make sure to check the opening hours before going. Opening hours changes by the season, and it’s usually no point in being up there after dark. We purchased tickets on site, but you can also buy online here or get the San Gimignano pass if you plan to visit more attractions.
Back down, it’s time for dinner. There’s no shortage of places to eat, and while it’s nice to just stroll through the narrow, medieval streets popping into whatever place looks cosy, making a reservation might be a good idea. We dined at Il Feudo on our first evening, and I can highly recommend. It was also very accommodating with my partner who has celiac disease (IYKYK).
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Day 2: Horseback riding, wine tasting and views
The main focus of your full day in San Gimignano should be to see more of the area, but at a relaxed pace. The hilltop town is surrounded by farmland, hills, gorges and valleys and is utterly beautiful.
If your evening before didn’t get too late, try to get up early for a sunrise walk. There’s something special about seeing a place wake up with barely anyone else around. A perk of travelling in autumn meant that sunrise wasn’t even that early.
Horseback Riding
Tell me a better way to spend an hour or two, than up and down the hills between the vines on a horseback, with the towers of San Gimignano as a backdrop?!
The landscape here is as made for horse rides and luckily there are several way to make it happen. We booked our one-hour tour directly by e-mail to Agriturismo Il Vecchio Maneggio and can highly recommend. It was my partner’s first horseback ride ever, and the gentle horse and our skilled guide made it a breeze.
You can also book tours combined with wine tasting, lunch and more on San Gimignano Exeperience here, or on Get Your Guide here.
San Gimignano’s Panoramic Roads
Now, it’s time to stretch your legs a bit. And make sure to have your camera ready. While there are picturesque views wherever you go, some places are even better than others. One of them is the Via Cortennano. A gravel road just outside town, popular for easy cycling tours. We stopped by here by car after our horseback ride at Il Vecchio Maneggio.
The other is Via Vecchia per Poggibonsi, often just called Via Vecchia. It’s an easy walk from town and takes you through lush farmland with panoramic views up to the towers on the hill.
Wine Tasting
Wine tasting is a must when in Tuscany, and there are several places you can do it in and around San Gimignano. Some places also offer combinations of lunch and wine tasting, tours through the wines and picnics.
A walk on the Via Vecchia can for example be combined with wine tasting at Tenuta Guardastelle. We didn’t stop here but walked through the farm to make a roundtrip back to town, and it looks exactly like I’d imagined a Tuscan winery would look like.
As the afternoon comes to an end, it’s time to head back into the old town again. Stroll the ancient streets, sit down for an aperitivo on one of the piazzas and enjoy yet another delicious dinner. On our second night, we went to Le Vecchie Mura – another lovely restaurant known for its gluten free cuisine.
A Quick Travel Guide to San Gimignano
I hope that by now you realise why it’s worth spending a couple of days in San Gimignano instead of just a few hours on busy day trip. So what about the practical details of visiting? To make your travel planning a bit easier, you find my best tips below.
When to Go
You can visit San Gimignano year-round. Winter is low-season and sees the least crowds, but bear in mind that some facilities may be closed this time of year. Summer, from mid-June through August, is peak season with more crowds and hot weather.
My recommendation is to visit either in spring or autumn, when there is a bit less tourists than in summer and the mild temperatures are perfect for exploring. I visited in mid-October and it was great. The old town was still busy during the day, but outside of that it was quiet and relaxed. We walked around in t-shirts during the day and dined outside wearing a jacket at night.
And not to forget, Tuscany dressed in autumn colours is something everyone should experience!
How to Get Here
I highly recommend having a car when visiting San Gimignano. While it’s possible to go by bus from for example Florence, it will take longer and you must swap busses along the way. Having a car available also makes getting around the area much easier.
Larger hubs such as Florence and Pisa are less than 1,5 hours away, and Cinque Terre just an hour more.
Check out my tips for first-time visitors to Rome
Parking
The only downside with driving, is parking. Like in other popular historic cities, parking is always a bit of a hassle.
Driving inside the old town is prohibited. Luckily, there are several parking lots just outside. They are signposted and easy to find and prices differs a bit from place to place. The closer to the old town, the more expensive and fuller the parking lot will be.
The best time to find a good parking spot is early morning or late afternoon. To avoid the whole parking problem, try to find accommodation with parking.
Where to Stay
There are plenty of places to stay in and around San Gimignano, from hotels to agritourismos (farmstays). The best location, in my opinion, is outside but within walking distance of the old town.
I love a good view and opted for the Bed & breakfast La Cornice, a 10-15 minutes’ walk from the town centre, and can 10/10 recommend. It’s such a lovely family run place with a strong focus on responsible tourism, only a few rooms and the most beautiful garden with lots of quiet places to sit and enjoy the view of the towers. It also had a small parking lot where guests could park to an extra cost, which is well worth it.
For a more rustic but upscale stay, I would check out Tenuta Guardastelle. The place I mentioned for wine tasting.
Wrapping up Two Days in San Gimignano
Writing this article and going through all my photos again have made me want to return to San Gimignano asap, and I hope I’ve inspired you too. This stunning medieval town is worth more than a couple of hours and the surrounding area has so much to offer whether you’re into sporty activities, beautiful views or food and wine.
Stay overnight, discover the region during the day and visit the medieval town when the day trippers have gone home.
Frequently Asked Questions
Is San Gimignano worth visiting?
Absolutely! San Gimignano is one of Tuscany’s most beautiful medieval towns, famous for its towers, cobblestone streets and stunning countryside views. Despite being a popular tourist destination, it’s well worth visiting, especially if you stay overnight.
How many days do you need in San Gimignano?
You can see the main attractions in a few hours, but I recommend spending at least two nights in San Gimignano. This gives you time to explore the medieval town without the day-trip crowds and discover the beautiful surrounding countryside.
Can you visit San Gimignano without a car?
It is possible to get to San Gimignano by public transport from Florence or Siena, usually by taking a bus via Poggibonsi. However, having a car makes it much easier to explore the surrounding countryside, wineries and smaller villages.
What is the best time of year to visit San Gimignano?
Spring (April–May) and autumn (September–October) are ideal for visiting San Gimignano. The temperatures are generally pleasant, and there are fewer tourists than during the busy summer months. October is particularly beautiful with the autumn colours in the surrounding countryside.
Is San Gimignano very crowded?
San Gimignano can get extremely crowded during the day, especially in summer and on weekends. However, early mornings and evenings are much quieter once the day-trip visitors have left. Staying overnight is the best way to experience the town without the biggest crowds.
Can you climb the towers in San Gimignano?
Yes! Torre Grossa is the tallest surviving tower in San Gimignano, standing 54 metres high, and the only historic tower open to visitors for climbing. From the top, you’ll enjoy spectacular views over the medieval rooftops and Tuscan countryside.
Where is the best place to stay in San Gimignano?
I recommend staying just outside the historic centre, within walking distance of the town. This way, you can enjoy beautiful views of the medieval towers, a quieter atmosphere and easy access to the old town. Some accommodations also offer private parking, which is a big advantage if you’re travelling by car.
