The 7 Best Things To See In San Gimignano

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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San Gimignano and vineyards

Nestled atop a hill in the Val D’Elsa amidst the stunning Tuscan landscapes, is the beautiful medieval walled town of San Gimignano. Located in the Italian province of Siena, it takes a mere hour in the car to drive from the Tuscan capital of Florence to San Gimignano where you will be treated to a taste of Italy at its finest. 

Bursting with picturesque sights and scenery, this place is home to some of the most famous landmarks in Tuscany, such as The Torri di San Gimignano. These remarkable structures are spectacularly-well preserved gothic towers that endow the town with a captivating skyline that is sure to take your breath away.

And if that isn’t enough to tempt you to pay a visit to this little haven, its elevated position treats visitors to magical views over the gorgeous Tuscan countryside, so you can enjoy some delicious Italian cuisine while taking the time to appreciate the town’s special setting. Offering elegance alongside quaint ambience, this town is bustling with locals going about their day-to-day lives alongside tourists wanting to catch a glimpse of its beauty. 

If you are wanting to plan a visit to the town but are not sure where to start, we have rounded up a list of the top 7 things to see in San Gimignano. Whether you are looking to chill out and enjoy some delicious local delicacies or have an action-packed sightseeing holiday, this town is one of the many places in Italy that is simply not to be missed out on.

  1. La Rocca di Montestaffoli 

A captivating fourteenth-century hill-top fortress, La Rocca di Montestaffoli lies a small climb from the town’s central square, Piazza del Duomo, and is a fantastic place to visit while you are in the area. Constructed back in 1353 by the Florentines, this landmark used to play a very important role in protecting the town by keeping a watchful eye on potential invaders.

Just 202 years later in 1555, the fortress was demolished and all that remains of the building is its shell. Along with being a stunning piece of architecture, the structure is surrounded by gorgeous olive groves and is known to attract artists and musicians alike who fill the area with the most romantic of atmospheres. 

Due to its hilltop location, La Rocca di Montestaffoli also boasts incredible views over the town’s spectacular architecture and winding streets, along with the beautiful verdant landscapes that surround it. Try to visit the landmark during the summer months as it turns into an outdoor cinema, catching a showing at this idyllic landscape is easily one of the best things to do in Tuscany, never mind San Gimignano

2. Vernaccia di San Gimignano Wine Experience 

While in the area, don’t miss out on the Vernaccia di San Gimignano Wine Experience; a museum that shares the history of the town’s delicious local wine, Vernaccia. Situated at Rocca, this attraction lies a stone’s throw away from La Rocca di Montestaffoli so it’s a great idea to get out early and visit both attractions on the same day.

A refreshing, dry white that is bursting with crisp notes, Vernaccia is the perfect drink for a hot day. Don’t worry, the glasses are sure to be in plentiful supply at the Vernaccia di San Gimignano Wine Experience. There are lots of different tasting opportunities for you to choose from depending on how much time and money you are looking to spend, with options including the Easy Wine Tasting, Superior Wine Tasting and the Top Masterclass.

If you are wanting to get an extra-thorough understanding of the wine and leave a Vernaccia expert, you can arrange a meeting with one of the sommeliers during your visit. After the Vernaccia di San Gimignano Wine Experience, you may well be inspired to explore the other local refreshments that the area has to offer and fancy visiting a winery near San Gimignano. There are lots nearby where you can get up close and personal with the grapes of your new favourite drink, with San Quirico Winery just 3 kilometres from the town centre.

If you are looking to tour some of the other fantastic wineries in the area, be sure to check out our list of The 8 Best Vineyards to Visit in Tuscany.

3. Cathedral of San Gimignano

Shouldering the Town Hall in the Piazza del Duomo is the Duomo di San Gimignano, which translates to the Cathedral of San Gimignano. Despite its name, it is not quite a cathedral but a predominantly Romanesque church.

In keeping with the period, the architecture is stylish yet understated and the real masterpiece of the structure lies in its interior. Once inside the building, you will find the walls to be adorned with magnificent 14th-century fresco cycles that depict stories from the New and Old Testaments of the Bible. 
While visiting the Duomo di San Gimignano, also known as the Collegiata di Santa Maria Assunta or Collegiate Church of the Assumption of Mary, be sure to check out Santa Finta; a small chapel inside the church that is filled with stunning artwork. The pieces have been credited to three prominent artists from Florence, one of which was an architect, another a sculptor and the last one, a painter

4. The Torre Grossa

Translating to ‘Fat Tower’ in English, the Torre Grossa dates back to 1298 and stands at an impressive height of 54 metres, earning it the title of the tallest tower in San Gimignano. Journeying to the top of Torre Grossa by foot is certainly quite the trek, with no less than 218 stairs required to take you to its crown, but as you can imagine, you will be rewarded with some spectacular views.

The scenes from the top are absolutely fantastic; between the rolling Tuscan hills and a panoramic view of the town, you really are in for a treat. If you’re not up for the challenge of taking the stairs, there is always the option of skipping to the good part without breaking a sweat by zooming up to the top using the tower’s elevator.

Back in the day, there were 72 towers similar to the Torre Grossa, each of which was constructed by rich, influential families in the town as a testament to their power and privilege. Flash forward to the present and only 14 of these towers remain, but they make great viewpoints for taking in the town and getting to appreciate the full glory of its surrounding landscape.

5. Torre e Casa Campatelli 

Torre e Casa Campatelli, which translates to ‘Tower and House of Campatelli’, is another of San Gimignano’s famous monuments. Unlike most of the buildings in the town, the building around the tower actually dates back to the 18th century instead of medieval times, so it adds a splash of alternative architecture and is a great place to visit to catch a glimpse of the unique features of each time period.

The tower itself was built during the 12th century and originally stood 11m high before it was extended to 28 metres. The wealthy Campatelli family purchased the building in the 18th century and turned it into the luxurious family home that you see it as today, decorated with lavish furnishings and fascinating art pieces.

During your visit, you will be able to listen to stories of San Gimignano’s past through educational videos that are screened in the building’s attic. These resources offer a unique chance to get an insight into the area’s fascinating history while standing in one of its very relics.

6. Church of Sant’Agostino

Towards the northern end of the town near Piazza Navona lies Basilica di Sant’Agostino, which translates to the ‘Church of Sant’Agostino’ in English. Encircled by houses, this 13th-century brick church sits in a square of the same name and offers a tranquil place to catch a break from the hustle and bustle of the town.

Being the second-largest religious building in the town (after the Duomo di San Gimignano),  you will be able to take in magnificent views of the town from the Church of Sant’Agostino’s many lookout points. Just like the Duomo, the exterior of the Church of Sant’Agostino follows the gothic style and appears very unpretentious and unassuming from the outside, as the magic lies in its interior.

The walls are embellished with spectacular frescoes that burst with colour and bring the church to life. Keep a special eye out for the work of the renowned Tuscan Renaissance painter, Benozzo Gozzoli, whose pieces can be found just behind the altar.

7. Centro Storico: Piazza della Cisterna 

Certainly not to be missed out on, Piazza della Cisterna is the main square in San Gimignano and sits right in the historical centre of the town. The area is a unique triangular shape, bordered by medieval towers and luxurious houses.

Here, you will be able to cool off by grabbing some tasty gelato while doing some people watching and taking in the beautiful architecture around the square. Being a key meeting place and cultural hub for locals and visitors alike, the Piazza della Cisterna has a delightful buzz during the day and night. 

The square also plays host to lots of events every year including festivals and tournaments, causing the town’s ancient architecture and medieval past to overlook the day-to-day hubbub of the area’s present. Piazza della Cisterna is also home to some of the best hotels in San Gimignano, Italy, so it is definitely worth checking out if you are looking for a place to rest your head for the night!


A truly magical place to visit, San Gimignano is easily one of the most beautiful towns in Tuscany, offering its visitors the exciting opportunity to explore medieval skyscrapers and stunning architecture while sampling some delicious local wine. Whether you are wanting a romantic getaway, a solo adventure, a trip with the kids or a break with friends, there is certainly something for everyone in this special town.

If you’re hoping to take a trip to Tuscany and visit beautiful towns like San Gimignano, get in touch with Italy4Real and speak to a member of our team for personalised advice and help planning a bespoke trip.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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