San Gimignano, Tuscany: Why You Should Eat, Play & Stay Longer Than a Day

There are so many day trips from Florence you can take to see more of Tuscany, and one of our favorites is from Florence to San Gimignano and the “city of beautiful towers”. It’s easy to get to and a fun way to spend a day. But being fans of slow travel in Tuscany that we are, there’s more to San Gimignano than you might realize - enough to keep you busy for an overnight or two, so you can get a better feel for one of the prettiest hilltop towns in the region.

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Getting To San Gimignano

 

We recommend you rent a car and enjoy the drive. The distance from Florence to San Gimignano is around 60 km from the airport and takes about an hour. (Add link to Driving in Tuscany article). Depending on your budget, and whether or not you’d be comfortable driving in Italy, there are of course other ways of getting there, but we love the freedom of driving and staying late.

You can also take a bus at Busitalia SITA Nord Autostazione next to the train station in Florence. You’ll still have to change to the local bus at the station in Poggibonsi but the timing between buses is much better than the train/bus combo. This’ll take 2-2.5 hours which is easy and inexpensive to boot.

Lastly, there’s the train from Florence to San Gimignano. It’s a little confusing as the train doesn’t actually go to San Gimignano. It stops in Poggibonsi where you transfer to the local bus to get you the rest of the way. This takes about 2 hours, but may end up being longer when the train and bus schedules don’t coincide. 

 

History of San Gimignano

 

As San Gimignano comes into view you realize that it’s not just another typical walled Tuscan city on top of a hill. The unique skyline with 14 of its original 72 towers still standing sets it apart from others we’ve visited. The towers were originally built between the 12th and 14th centuries by the ruling families as signs of their wealth and power, and to outdo one another as in “my tower is taller than your tower”. When the city lost its autonomy to Florence, the Florentine government made the owners shorten their towers or knock them down. Disrepair and time have done the rest but the 14 that remain are truly a tribute to the city’s history.

 

Today, the town is one of the most visited towns in Tuscany during the busy season, which means lots of tour groups, buses, and crowds. Let’s face it, this part of Italy can be like that. But it doesn’t have to be. There are plenty of less crowded and authentic places to visit in Tuscany which we’ve written about before. But San Gimignano is popular with tourists for a reason, and there are ways to enjoy it without the crowds. 


Slow Travel Tip: Stay the Night (or even two)

 

If you only have time for a day trip and don’t like heavy crowds, try and arrive in town earlier or later in the day. Take the morning to explore the countryside then stroll the town later that afternoon when the tour buses leave.

But San Gimignano deserves more than a day trip and here's why:

San Gimignano, Tuscany, Italy
  • It's one of the most romantic hilltop towns in all of Tuscany, the kind you see in those romantic movies about Italy
  • Staying longer means seeing more of the town than just a few streets and towers
  • Night time in town offers unbeatable photo ops and a stunning Old World feel
  • Florence isn't the only Renaissance city in Tuscany, and San Gimignano is a nice break from the bustling capital city.
  • There are enough good restaurants, wine bars, and gelaterias to keep you happy for days
  • You'll find many slow travel experiences in the bucolic countryside near here, including farm-to-table and authentic food experiences 

Things To Do in San Gimignano


1. Self-Guided Walking Tour of San Gimignano

There’s no shortage of things to do in San Gimignano. The city is laid out north to south with parking lots at either end, so no matter which one you start from, everything is an easy walk. Along the way from either direction there are plenty of shops, some with creations by local artisans, coffee shops and gelaterias, wine shops, small cafes and fine restaurants. 

San Gimignano, Tuscany, Italy

Take your time and head for the Historic Centre of San Gimignano, a designated UNESCO World Heritage Site. Make your way to Via San Matteo if coming from the north or Via San Giovanni if coming from the south. Don’t be shy about venturing on to the side streets. Some of the off the beaten path shops and cafes are worth finding, and the narrow streets and medieval architecture are amazing.

San Gimignano, Tuscany, Italy

You’re in the historic center when you reach the Piazza della Cisterna, a triangular shaped plaza with a central octagonal shaped well and red brick pavement. The well is surrounded by the medieval tower houses that belonged to the city’s noblility. At one time there would also have been taverns and assorted workshops. This Piazza grew around the junction of two of the most important roads of the time - the road from Pisa to Siena and the Via Francigena, a pilgrimage route that connected Canterbury to Rome. This was a busy place with its central market and events like festivals and tournaments. Standing here can take you back in time to imagine what life must have been like in the city’s heyday. Well maybe not too far back as we enjoy a gelato from what is arguably the best gelateria in town.

A short open passageway connects to the Piazza del Duomo, the historic center of politics and religion. After the passageway, on the left is the Palazzo Comunale dating from the late 13th century which serves as city hall. When its open you can tour inside to see beautiful frescoes as you go from room to room. 

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Near this Piazza look for a pair of tall towers standing side by side. These twin towers, the Torre Gemelle (aka the Salvucci Towers), are over 700 years old and might be the most famous towers in the city. They were built by the Salvucci family to show their wealth and importance but a rule at the time said that towers could be no taller than the old city hall tower. These two were built a bit shorter than the city hall tower. The base of one starts at a higher elevation than the base of the other. When viewed from a certain angle, one tower can be superimposed on the other, giving the appearance that the Salvuccis had the tallest tower around. 


2. Climb the Torre Grossa

Attached to the Palazzo is the Torre Grossa, a 177 feet tall tower that you can climb inside to the top. This is well-worth the effort. The view is amazing, all those tiled rooftops and a spectacular view of the surrounding Elsa Valley. We climb to the top every time we visit just for that view of this part of Tuscany. Don’t pass this up.


3. Shop for Tuscan Specialties

Shopping in San Gimignano is not as extensive as Florence, but the limited array of shops is actually a plus in my book. I felt much less overwhelmed here and enjoyed spending more time browsing and visiting with shop owners. The southern end of San Gimignano is the more commercial part of town, and you’ll find a concentration of shops along Via San Giovanni. Shop for authentic Florentine leather goods (Le Torri is one of the best), Tuscan ceramics and pottery, hand marbled paper and hand handcrafted jewelry. Visit Macallè for uniquely crafted silver jewelry. Food specialties like truffles, cured meats (look for wild boar), and cheeses are also plentiful and popular, though you'll probably eat them long before you leave the country.


4.  Visit the Basilica: Combined Periods of Art and Architecture

Right next to the Palazzo are the massive steps to the Duomo, formally the Basilica Collegiata di Santa Maria Assunta. It has stood here since the 11th century and in its present form since the 13th century. As you would expect, the structure is in the form of a Latin cross. Inside it is made of alternating black and white marble. Most of the artwork is from the 14th century with some painted vaults in lapis blue with gold stars while other areas have mostly intact frescoes. We have visited many churches but this one is simply beautiful.


5. Vernaccia Winery Tour & Tasting

Vernaccia wine tasting, Capella Sant’Andrea winery, San Gimignano, Tuscany

There are several wineries near San Gimignano, and local producer Capella Sant’Andrea is the perfect place to discover the area’s authentic wine, Vernaccia di San Gimignano. It’s considered one of the best Italian white wines and is unique to San Gimignano. Even if you don’t normally drink white wine, you should try it. It tends to be full-bodied, dry, a bit minerally with a beautiful golden color, and it goes great with an aperitivo.

 

6. Grab a Map and Drive

One could easily spend a day driving the Tuscany roads around San Gimignano, discovering farms, agriturismos, and country homes. Not to mention the many gems along the way so hidden you might think you're trespassing. But the sign invites you in to taste their homemade cheese, wine, or pasta made fresh that day. Go! The photo ops alone are a great way to spend the day.

 

7.  Stay Late for Aperitivo

Aperitivo, San Gimignano, Tuscany, Italy

When the crowds leave for the day is the perfect time for a glass of wine or an Aperol Spritz with aperitivo. D!Vineria is small with an amazing view, serving yummy small plates and cold meat platters. Divornum Wine Bar is also fun with a lively atmosphere. Get there early at both places for a table with a view and watch everyone else leave as you breath a sigh of relief. 


8.  Snap Beautiful Night Photographs

San Gimignano is a place that naturally lends itself to dreamy night photography, with its shadowy back streets and arched alleyways glowing with warm streetlight. It’s the perfect time to shoot street scenes in town with just a few people in them instead of crowds.


Where To Stay in San Gimignano

San Gimignano vineyard, Tuscany, Italy

For an experience that's authenticly Tuscan, consider staying at one of the many bed-and-breakfasts or agriturismos in the surrounding countryside. Fattoria Poggio Alloro gets high marks for it’s authenticity and producing a variety of Italian specialties onsite.

For more amenities, there are several very good small boutique hotels. The small hamlet of Pancole is ideal as a base to explore, and just minutes outside San Gimignano.

 

 Photo: Hotel La Cisterna, San Gimignano

Photo: Hotel La Cisterna, San Gimignano

In Town:

Hotel La Cisterna is centrally located in the heart of town, with romantic rooms and some of the most breathtaking views of the town and towers. Check details and rates.

 Photo: Hotel L'Antico Pozzo, San Gimignano

Photo: Hotel L'Antico Pozzo, San Gimignano

If you want to stay in the historic town, the Hotel L'Antico Pozzo has spacious, affordable and quiet rooms. Check rates and more details

 


Minutes from San Gimignano:

 

The Hotel Le Renaie is located in Pancole, just 5 minutes from San Gimignano, with comfy rooms (some with terraces), a pool, and an excellent on-site restaurant Leonetto for breakfast (included in room rates) and dinner. Check rates and details, and our full review here.  

Hotel San Michele is 1.5 km from San Gimignano, and a casual country inn run by two sisters Paula and Roberta. The property is small and quiet with nice grounds and a beautiful pool. You could even walk or bike to town! Check details and rates.

 Photo: Hotel La Collegiata, San Gimignano

Photo: Hotel La Collegiata, San Gimignano

Casa Lari in Pancole has well-appointed apartments of different sizes, and a lovely pool. Though there's no restaurant, it's right next door to Hotel Le Renaie's excellent restaurant, Leonetto. Find details and rates here.

Hotel Casolare Le Terre Rosse is a stunning country home with large pool, just five minutes from San Gimignano. Check out details and rates.

Hotel La Collegiata is just 2.3 km from San Gimignano, with a beautiful pool, on-site restaurant, and incredible grounds There's also a fitness area and massage available to really pamper yourself! Check out rates and details.

Booking.com

 

Where to Eat in San Gimignano

 

The restaurants in San Gimignano all offer some variation on local Tuscan cuisine. For an authentic local specialty, try a dish with Cinghiale, or wild boar. Delicioso!

Dessert, San Gimignano, Tuscany, Italy

La Mandragola - Off a quiet side street, reserve a table outside in the beautiful courtyard.

Caffe' Giardino - perfect for breakfast or light snacks.

Osteria della Cantene

Gelateria Dondoli - Known for their signature flavor, saffron cream, Crema di Santa Fina, and Vernaccia sorbet

Gelateria Dondoli, San Gimignano, Italy

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