San Gimignano Day Trips from Florence

Known as the Manhattan of medieval times, San Gimignano is one of the most visited towns in Tuscany. Take the opportunity to visit it during your trip

Isabel Catalán

Isabel Catalán

11 min read

San Gimignano Day Trips from Florence

View of San Gimignano | © LigaDue - Wikipedia

Italy is one of the most beautiful countries in the world, but if there is a region whose history, medieval villages, gastronomy and landscapes fascinate travelers, that is Tuscany.

Take advantage of a trip to Florence to explore some of the most emblematic destinations in Tuscany such as Pisa, Siena, Chianti or San Gimignano on a day trip by bus.

Best day trips to San Gimignano from Florence

Piazza Cisterna, San Gimignano| © cfwee - Flickr
Piazza Cisterna, San Gimignano| © cfwee - Flickr

Known as "the New York of Tuscany" for its imposing stone towers, the medieval town of San Gimignano is located just 60 kilometers from Florence and thanks to its beautiful dreamy old town is a top destination to visit during a trip to this emblematic Italian region.

Here are the main organized excursions to discover San Gimignano and the magical Tuscany.

Day trip to San Gimignano, Siena and Chianti (lunch and wine tasting included)

Siena| © Cristina Gottardi
Siena| © Cristina Gottardi

A road trip to Tuscany is one of the most romantic experiences to do in Italy. This is a land of green meadows, rolling hills and vineyards stretching in all directions, charming little villages and delicious gastronomy that will make you sigh.

If you want to let yourself be seduced by the magic of Tuscany, this day trip to San Gimignano, Siena and Chianti from Florence is one of the most complete tours you can take, because for a very reasonable price you will not only visit in one day some of the greatest pearls of the region (Siena, San Gimignano and Chanti) but you will have the opportunity to enjoy a delicious traditional lunch and a tasting of regional wine and olive oil in a beautiful winery in Chianti.

Why I like this tour

One of the advantages of Florence's geographical location is being able to visit some of Italy's most charming towns and cities that are located in the surrounding area. In Tuscany there are real gems lost among the hills that exude art on all four sides and that every traveler should enjoy at least once in a lifetime (although I warn you that this region hooks!)

With this day trip to San Gimignano, Siena and Chianti by bus you will take an unforgettable and complete memory of your trip to the beautiful Italian Tuscany for an affordable price and you will not have to worry about planning travel or lunch during the route, as it is included. You will save time and money that you can spend on other things, which is always nice!

In addition, when it comes to knowing the tourist attractions that are part of this tour, it combines the formula of a guided tour with free time in the different cities that the excursion covers, which is a very interesting option to consider if you want to enjoy the advantages of both modalities.

What to expect

You will leave Florence early in the morning (at 8:45 AM) to take the coach with your group to these emblematic Tuscan towns that played such an important role in the Middle Ages and the Renaissance, which is why this region is such a mine of history and art!

Get ready because along the way you will travel through the bucolic countryside filled with vineyards that have inspired many artists, stroll at your leisure through the medieval town of San Gimignano (known as "the New York of Tuscany" for its impressive towers), you will visit the fortress of Monteriggioni (one of the best preserved medieval complexes in Italy that has hardly changed since the 13th century), tour the small village of Chianti to visit a winery where you will participate in a wine tasting and have lunch with regional specialties.

Finally you will go to Siena, Tuscany's medieval treasure and home of the famous Palio horse race. Here you will explore the historic center accompanied by a guide who will show you all the secrets of this beautiful monumental city and such impressive places as the Duomo, Via di Citta, Piazza and Palazzo Salimbeni, Palazzo Tolomei, Piazza del Campo and Fonte Gaia, Palazzo Pubblico and the Civic Museum of Siena.

What is included in this tour

  • Travel by GT air-conditioned coach.
  • Expert multilingual escorts.
  • Guided tour in Siena with monolingual guide in English or Spanish.
  • Free time in San Gimignano.
  • Visit to the fortress of Monteriggioni.


  • San Gimignano
  • Monteriggioni
  • Chianti, with tasting of its wine and typical products
  • Siena

Book your excursion to San Gimignano, Siena and Chianti

Day trip to Pisa, Siena and San Gimignano (with lunch and wine tasting)

Pisa| © Andrea Cevenini
Pisa| © Andrea Cevenini

Medieval villages that captivate the soul, fertile valleys and landscapes covered with vineyards, colorful sunsets, a gastronomy that takes your breath away... Leaving Florence and choosing a destination among all the corners of Tuscany to spend the day seems an almost impossible task. This Italian region is a treasure trove of art and culture that is virtually unfathomable.

What's there to resist when it's so easy to fall in love with everything in Tuscany? As a traveler, I've asked myself this question more than once, but fortunately there are activities like this day trip to Pisa, Siena and San Gimignano that won't make you give up anything during your trip.

You will travel through the green plains of Tuscany to Siena (the artistic pearl of Tuscany and a World Heritage City), enjoy a delicious Tuscan lunch and wine tasting in a charming wine cellar-restaurant in Poggibonsi, visit the medieval town of San Gimignano (famous for its impressive towers) and visit Pisa (known worldwide for its leaning tower). What more could you ask for?

Why I like this tour

If you have never visited this famous Italian region before, the most complete way to get to know its culture, traditions and all the must-see sites of Tuscany such as Siena, Pisa or San Gimignano in just one day is by taking this tour.

It's all advantages! You won't have to worry about organizing your transfers (as you will travel comfortably from one place to another by bus) or stops to eat and rest (as this tour includes a traditional Italian lunch and wine tasting), or finding the main tourist attractions to see. Everything is perfectly planned for you to enjoy the experience to the fullest!

In addition, this tour combines in an excellent way the formula of a guided tour with free time in the different cities covered by the tour, which is a very interesting option to consider if you want to have the advantages of both modalities.

What to expect

At 7:45 AM you will leave Florence by bus for Siena, the so-called "Red City", where you and a guide will visit the historic center and monuments such as the Duomo, Piazza del Campo and Fonte Gaia or Palazzo Tolomei, among others.

Afterwards you will stop in Poggibonsi for a break and lunch in a nice winery. Besides tasting typical Italian dishes you will have the chance to participate in a Chianti wine tasting, a truly fantastic and fun gastronomic experience!

The next stop on this tour is San Gimignano, a medieval hilltop town with the best skyline in Tuscany. I'm not exaggerating! Its spectacular medieval towers that stoically stand the test of time are visible from the road.

During the walk through San Gimignano you will have the feeling of being immersed in a movie set. Not for nothing is it considered one of the most beautiful villages in Tuscany. Enjoy free time to lose yourself in its beautiful medieval streets, contemplate gems such as the Piazza della Cisterna or Porta San Giovanni, visit the Duomo or climb one of the famous towers. The views from the top are amazing!

Finally you will visit Pisa and its impressive Piazza dei Miracoli, where you can admire the Duomo and the Baptistery as well as the famous leaning tower that has made this city world famous.

Isabel's Traveler Tip

By the way! Don't forget to have your picture taken holding the Leaning Tower of Pisa. It's a tradition that every traveler must do in Italy.

What is included in this tour

  • Air-conditioned bus
  • Professional guide
  • Guided tour of Siena in English and Spanish only
  • Lunch and wine tasting at Poggibonsi
  • Visit to San Gimignano and Pisa


  • Siena: Piazza del Campo, Fonte Gaia, the Duomo, Palazzo Tolomei, Via di Città and its historic center.
  • Poggibonsi: traditional Tuscan lunch in a local winery located halfway between Siena and San Gimignano. Menu based on bruschetta, salami and fresh cheese as starter, tagliatelle with ragù sauce (on request with tomato) as first course and dessert. Wine and water included.
  • San Gimignano: Piazza della Cisterna, Piazza del Duomo, Torre Grossa and Porta San Giovanni.
  • Pisa: Piazza dei Miracoli, the Duomo, the Baptistery and, of course, the Leaning Tower.

Book your tour to Pisa, Siena and Chianti

Day trip to Siena and San Gimignano

Panoramic view of Siena| ©Alevision Co
Panoramic view of Siena| ©Alevision Co

Tuscany is one of those corners of Europe where everything is worth seeing. It has sublime landscapes of green meadows and vineyards, spectacular gastronomy and historically significant villages of unparalleled beauty that are easy to fall in love with.

But as with any trip, sometimes you have to choose because it is not always possible to take in everything you would like to. So, if during your trip to Florence you have limited time to tour this mythical Italian region, my advice is to take this day trip to Siena and San Gimignano.

Why I like this tour

With this tour you will see the highlights of both locations and explore the beautiful Tuscan countryside with the advantages of traveling in a small group and having the assistance of a guide for part of the tour, specifically in Siena.

Thanks to your guide you will learn first hand everything you want to know about the main sites of interest but you will also have free time to customize the tour in San Gimignano and go at your own pace, getting lost in its beautiful medieval streets and stopping wherever you want and whenever you want. It is a very interesting option to consider if you like to combine both types of visits.

In addition, you will live the experience of having lunch in an authentic Tuscan winery where you can taste the excellent wines of the region, relax for a while chatting with the group and taste a bit of that "buona vita" Italian style that has crossed borders. Sounds wonderful, doesn't it?

Another highlight is that on the way back to Florence, as the bus has free Wi-Fi, you can take the opportunity to upload to your social networks all the photos and videos of the excursion, which I can assure you will be many because Tuscany is a fascinating land that raises real passions.

What to expect

To make the most of the day, the tour departs early from Florence (at 8 AM) for Siena. You will have to get up early, but even if it is tempting, I do not advise you to take a nap on the bus because along the way you will see a beautiful rural landscape between hills and vineyards, a prelude to that "Gothic dream" that is this World Heritage City.

When you arrive you will believe that time in Siena seems to have stopped in the 13th century. It is an incredible city! During the guided walking tour of the historic center you will see important monuments such as the Piazza del Campo and Fonte Gaia, the Duomo and Palazzo Tolomei, among others, and watch out for stories about the Palio di Siena festival because it is more than just a horse race!

At the end and before lunch in an old typical Tuscan winery you will have time to see the fortress of Monteriggioni, a small walled village on a hill surrounded by olive trees that looks like something out of a fairy tale. In my opinion, one of the most beautiful sites of the tour, you won't get tired of taking pictures!

The last stop of the tour will be San Gimignano, the best preserved medieval citadel of the region famous for its skyline of large stone towers. The most iconic are Torre Grossa (for being the tallest) and Torre Rognosa (for being the oldest) although in the old town you will see other very cool monuments such as the cathedral, the palazzo del Popolo or the church of San Agostino.

Before returning to the bus that will take you back to Florence, I recommend going to the main street of San Gimignano because it is full of typical little shops where you can buy some souvenirs or an ice cream.

What is included in this tour

Day trip to Siena and San Gimignano from Florence in a small group

  • Professional English speaking guide and driver.
  • Round trip transportation by air-conditioned minibus or minivan with free wifi
  • Guided walking tour with free time in Siena
  • Tickets to visit the of Siena Cathedral (if option is booked)
  • Lunch at a Tuscan winery, along with its excellent red wines.
  • Free time in San Gimignano.


  • Siena
  • Monteriggioni
  • San Gimignano

Why San Gimignano is worth a visit

San Gimignano Museum 1300| ©Fracund - Trabajo propio
San Gimignano Museum 1300| ©Fracund - Trabajo propio

Although it may not have the fame of other Italian cities like Florence, Pisa or Siena, in my opinion San Gimignano is one of the most beautiful villages in the country and one of the must-see places in Tuscany. For a reason it was declared a World Heritage Site by Unesco.

The village can be covered in a couple of hours comfortably because it is not very big and is known especially for its landscape of stone towers, so high that can be seen even from the road before reaching the town. They have a curious origin and it is that they arose from a kind of competition between the wealthy families of the area to show which was the richest and most powerful.

Of the 72 that came to have during the Middle Ages, nowadays 14 are preserved and you can even climb some of them to contemplate the views of the surroundings. Something I recommend to admire from the sky both the magnificent architecture of San Gimignano and the beautiful landscape of cypresses, vineyards and olive trees that surrounds it.

In addition to its towers, during the walk through its charming medieval streets you will see other buildings such as the Duomo (which has wonderful 14th century frescoes), the Palazzo Comunale (home of the Civic Museum and from where you can enter the Torre Grossa), the church of San Agostino, the Cisterna square and the Rocca di Montestaffoli, which serves as a viewpoint of the town. The views from here are also fabulous, so take your time to take the photos you want and enjoy the moment.

There are many reasons to visit San Gimignano but I recommend it especially because during the visit you will have the feeling of making a trip back in time to the past, as it still retains that medieval atmosphere of great beauty that transports us to another era and catches.

If you like this excursion, you might be interested in

If during your trip to Florence you would like to make several excursions to get to know the surroundings of the city, I advise you to take a look at the article The 10 best tours and excursions from Florence to find inspiration for your next getaway.

However, in case you prefer to concentrate on your vacation in the capital of Tuscany to get the most out of it, don't miss the post The best things to see and do in Florence where we review the must-sees of the city such as the Duomo, the Uffizi Gallery or the Accademia Gallery, among many other emblematic places.

Frequently asked questions

  • Why should I visit San Gimignano?

    Known as the medieval Manhattan, San Gimignano is famous for its 14 towers, which contribute to its impressive skyline. It is also known for Vernaccia wine and the famous Gelateria Dondoli, an ice cream parlor founded by master gelato maker Sergio Dondoli, a former international champion gelato maker.

  • How far is San Gimignano from Florence?

    San Gimignano is about 60 km (37 miles) away from Florence, and it takes approximately 1 hour 20 minutes - 1 hour 40 minutes to get there, which depends on your means of transportation.

  • What souvenirs can I take home from San Gimignano?

    Vernaccia wine is an original product of the town of San Gimignano, and is a great souvenir to take home. Ceramics depicting the medieval skyline are also a nice souvenir of the architectural uniqueness of San Gimignano.