San Gimignano

Visiting this medieval hilltop town & why you should too!

6 min read

The majestic slender and sky-high medieval towers of this ancient village definitely have a story to tell, let’s start!

Us at the Piazza della Cisterna

A 30 minute drive away from La Torre, in Val D’Elsa, lies one of our favourite places to visit in Tuscany, the UNESCO World Heritage site named San Gimignano. The sun-drenched hilltown is full of history, culture, food and fun things to do, explore the medieval town with us. 

If you’re planning on touring Tuscany, it’s probably best to come just before or after summer, as during the summer period the slim alleys of Tuscany’s medieval towns can get a little cramped with tourists. The town is located between Siena and Florence so it becomes a popular stop when travelling to either of those cities; not only this but if you’re planning to travel the Via Francigena to Rome, you will also pass by San Gimignano. Although walking up and down hill may be tiring for those walking the Via Francigena, the high views from this hilltop become an opportunity to stare into the peaceful landscape of Tuscany; capturing the swaying trees, the beautiful birds flying over the rolling hills while enjoying a delicious ice cream from our favourite ice cream place so far, is a wonderful way to spend an afternoon or evening on holiday.

The History of San Gimignano

San Gimignano

Between the 11th and 13th centuries, many Italian aristocrats, noblemen and wealthy merchants had taken control of San Gimignano, as it was a vital firm point for pilgrims travelling the Via Francigena (for more information about what the Via Francigena is, click here). They had constructed around 72 towers, not only for defense against enemies, but as a symbol of their power and affluence. The first couple of towers built by rich families consisted of very narrow rooms (1x2m), without very many windows. The walls were made to be 2m thick to ensure keeping the rooms cool in the summer and warm during the winter period; the bottom of the tower had the family shop that was open for customers, the first floor consisted of the bedrooms and higher up the towers kitchens were made (so in case of a fire, they could escape down the stairs).

The town became well known for its production and trade of saffron, Vernaccia wine as well as Greek wine and wool. With the increase in revenue of the town, they invested in restyling the towers in the 12th century, to create more practical living spaces that were larger, with bigger openings and wooden balconies. Becoming an independent town in 1199 didn’t last very long before the Black Plague arrived in 1348, causing the number of inhabitants to dwindle from 13,000 people to two thirds of that! Therefore blowing its riches straight off of the hill. The Florentines took the weak town under its wing and saved it from being urbanised in the Middle Ages, where many historical towns were rebuilt for industrial uses.

The Black Death in Italy

A model displaying the reconstruction of San Gmignano, after the plague in the 1300s

The Great Plague of Milan, a monk visiting a victim of the plague

The amount of towers decimated from 72 to 13 due to low maintenance, although there were a few urban renovations done in the 15th century such as: the Rocca di Montestaffoli (a great wall covering the town in defense against Sienese attack), a couple of churches and buildings, despite this, San Gimignano experienced another economic catastrophe in 1631. The Great Plague of Milan had reached Tuscany, killing many people and leaving the town with only 3000 residents - making San Gimignano one of the poorest places in Tuscany. 

However, hope was not lost as during the 18th century the town focused on bettering its agriculture. The population size slowly started to rise to a whopping 10,000 residents (as recorded in 1948). During the 19th century many buildings were restored to its original strength, this was followed by a rapid growth of cultural tourism, held until today with the ‘Town of Towers’ millions of tourists each year. Now being a UNESCO World Heritage site the amount of tourism has augmented massively in the last decade as well as pushing San Gimignano to protect and preserve its medieval atmosphere and buildings with national laws such as the ‘Code of Cultural Heritage and landscape’, also with strict local regulations, for instance: limits on pollution, traffic and noise. Today, the town has over 8000 residents and thrives off of agriculture, prestigiously producing D.O.C.G Vernaccia wine as well as successful agriturismos scattered all around San Gimignano, from wine tastings and cooking classes to Piaggio tuk tuk tours.

We are so glad that San Gimignano survived throughout its falls in history, otherwise we'd have one less favourite place to visit!

Things to do in the Medieval Manhattan

Taste Vernaccia White Wine From its Home

The vineyards of the San Quirico Winery

Poetically written in the fine words of Dante’s Inferno, San Gimignano’s Vernaccia white wine is definitely a must try when visiting the town. The crisp wine is filled with citrus flavours that give a medium finish, refreshing for an aperitivo or an evening meal - or even better, we prefer to take away a glass of Vernaccia from the many enotecas sprad around the medieval alleys and savour the taste while gazing over the stunning panorama over the hilltop viewpoints. We have also experienced a San Gimignano wine tour where we got to try different wines such as Chianti Classico, Vernaccia and Brunello Di Montalcino, at the same time, learning about the wine making process from a sommelier. The scrumptious cheeses, the variety of salamis and bruschetta helped to keep us sober on the tour! We recommend visiting the Tenuta Torciano (8km from the center of San Gimignano) agriturismo or the San Quirico Winery (3km from the center of San Gimignano) for an unforgettable experience (we suggest to book in advance online or by calling).

Go on a Vespa Tour or a Piaggio Tuk Tuk Tour

Piaggio Tuk Tuk

Vespa Tour

What better way is there to tour San Gimignano, Tuscan style! There are a few companies where you can rent a vespa or a Piaggio tuk tuk for the day with a guide and explore the planned routes with your guide to witness the best scenery on the road, through the vineyards and olive groves. Maps are also provided with suggestions of great places to eat and relax in the calming countryside. We haven’t tried this experience yet but we know that vespa touring is a must do! You can choose to be the driver or just ride as a passenger, an aperitivo is usually offered at the end of the trip to provide a relaxing finish to a day full of excitement. There are a few companies that offer this experience, a good website to use to search and book your fun day out is viator.com

Climb the tallest tower still standing

La Torre Grossa, outside

La Torre Grossa, inside

Unlike taking an elevator to whisk us up to the top of the Eiffel Tower or the Burj Khalifa, we walk up a 13th century ‘skyscraper’. The Torre Grossa is 177 feet (54 meters) high, its construction started in 1298 and was completed in 1311. This is the only tower in San Gimignano that is available to access to the public. The tower has been conserved with rooms left how they were made; in the middle of the tall staircase located in the center of the tower, hangs a long screen showing a 3D video of different rooms in the tower, its structures and the art of the medieval era. We found this experience education and more fascinating the more we climbed the many staircases. If you're pasting the Piazza del Duomo in San Gimignano, its worth taking a stroll (more like a hike) in La Torre Grossa at a cheap price!

Have a blast from the past at the towns torture museum!

Museo della Tortura, San Gimignano

Although the museum may not be as theatrical as the London Dungeon, the exhibits of the Middle Age torture methods definitely made our spines tingle - as well as other things! The gruesome detail of wax models, art pieces and seeing the actual weapons of torture really helped us to empathise how criminals during the Middle Ages suffered. From medieval chastity belts to eye-gougers to knee splitters, whilst taking a stroll through this evil, we quickly understood that there were no human rights during the medieval era. The museum is split into two buildings one exhibiting the torture methods and if that wasn’t enough gore, the other displays ‘the pain of death’ with electric chairs and other horrifying death traps! Payment is taken at the door, if visiting in a group you will receive discount. Unlike most tourist places to visit in Italy, these two museums are also open during the winter on Saturdays and Sundays.

Or visit the museum of exotic birds

Inside the Ornithology Museum

For the squeamish and young children we wouldn’t advise exploring these past horrors. Not to worry, there is another family-friendly as well as educational museum in San Gimignano, the Ornithology Museum. Located in the former Church ‘San Francesco’, the 16th century Church has been converted into a museum displaying around 370 specimens of rare or endangered birds found in Italy and across Europe, the embalmed birds have been collected since 1866. Part of the large collection of embalmed birds was donated to the museum by Marianna Panciatichi Ximenes d’Aragona Paolucci during the 1920s, a Tuscan baroness. Being obsessed with nature and wildlife, we were captivated by how many different bird we got to see, it was a relaxing experience filled with new things to learn about Italy and Europe's wildlife.

Another family-friendly museum to visit is the San Gimignano 1300

Model of San Gimignano as it once existed

At the San Gimignano 1300 musuem, one can see the town at its peak before its fall downs due to the plagues. There is a huge clay model displaying the medieval town when it once had 72 towers. This masterpiece was visioned by history's arguably best artists, Michaelangelo and Raffaello Rubino, the model was then created by an amazing team of historians and artisans to produce what once was the 'empire' of San Gimignano. This museum helped us to understand the ways of living in the 12th - 14th century as well as why the majority of the towers collapsed and the importance of the Via Francigenas effect on the growth of San Gimignano. With so much to learn about this medieval town, we recommend taking a trip to this museum if you are intrigued by Italian history and architecture.

Delve into La Rocca di Montestaffoli

La Rocca di Montestaffoli

La Rocca di Montestaffoli is situated near Piazza del Erbe and is the remains of a fortress from the 14th century. The fortress was previosly owned by the Bishop of Volterra, until 1353 when the Florentines took control of San Gimignano after the Black Plague hit badly. Although the stronghold was partially destructed during the 'Grand Duchy of Tuscany', the remains were later repaired and restored by the 20th century where we can now savour the panorama of the Tuscan countryside. The open space is perfect for a picnic, as it is on the hilltop, we enjoyed a wild boar baguette while gazing over Tuscany's stunning scenery. Many artists and musicians set up their instruments and play for the public, the experience is truly magical, calming and such a great way to spend an afternoon! During the summer period, the Commune of San Gimignano set up an outdoor cinema for the evenings as well as concerts, we can't wait to visit when summer comes around again (hopefully covid will be gone by then)! Vernaccia wine tasting is also held at La Rocca di Montestaffoli, the purpose is to educate people on the wine, the process of making wine and the impact on emotions that wine causes. When visiting La Rocca we also learnt about the culture, territory and history of Vernaccia from San Gimignano, we would say that it helps to connect the city and the countryside in a fun way.

Try the delicious restaurants and best Gelato ever!

Lots of resturants that can offer you delicious Tuscan cuisine

If museum or history is not your cup of tea, you can simply enjoy your afternoon or evening sitting outdoor and enjoying a delicious meal. San Gimignano is filled with delicious restaurants from its entrance to the roofs of the towers! The Tuscan cuisine is spectacular and in San Gimignano the food is full of flavour, our go to restaurant in San Gimignano is Perucà, we made a restaurant review on Perucà, you can check it out here.

Our friends James and Sophie about to choose their luscious icecream

Aside from the luxury three course meals, a must try when visiting the medieval manhattan is its gelato! Located in Piazza della Cisterna, Gelateria Dondoli can be seen a mile away due to its extensive ques. They have extraordinary flavours such as saffron, pink grape fruit, Vernaccia, but the strangest flavour we've tasted is the 'Italian Garden' flavour. This flavour is a combination of tomato, cheese (most likely ricotta or mozzarella) and basil! Yes, we know this sound weird but honestly, it was mouthwatering, we order a scoop or two each time we visit San Gimignano! When our close friends James and Sophie came to visit us, we clearly had to take them to try this gelato and by no surprise they loved it!


Strolling through the medieval alleys with James and Sophie

San Gimignano is a popular tourist attraction for a reason, its culture, history and beautiful scenery makes it a perfect place to explore and taste the Tuscan countryside. With so many activities to do, whether it be eating, drinking wine, learning about what once was a medieval town, we are certain that the day will be worth your time and we are sure that you'll have fun too!