Day Trips to San Gimignano from Florence

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

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

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

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 sprawling vineyards, charming little villages and mouth-watering cuisine that will make you gasp.

If you want to 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 do, 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 also 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 the most charming towns and cities in Italy that are located in its surroundings. In Tuscany there are true gems lost among the hills that exude art from all four sides and that every traveller should enjoy at least once in a lifetime (although I warn you, this region is a must!)

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

In addition, when it comes to getting to know the tourist attractions that are part of this tour, it combines the formula of a guided tour with free time in the different cities covered by the excursion, 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!

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

Finally you will go to Siena, the medieval treasure of Tuscany and home of the famous Palio horse race. Here you will explore the historic centre 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

Itinerary

Medieval villages that captivate the soul, fertile valleys and vine-covered landscapes, colourful sunsets, 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 an artistic and cultural treasure trove that is almost beyond comprehension.

What's there to resist when it's so easy to fall in love with everything in Tuscany? As a traveller, 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 will make sure you don't have to 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 (world famous 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 organising your travel arrangements (as you will travel comfortably from one place to another by bus) or your lunch and rest stops (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!

Moreover, this tour is an excellent combination of a guided tour and 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 your guide will visit the historic centre and such outstanding monuments as the Duomo, Piazza del Campo and Fonte Gaia, Palazzo Tolomei, among others.

Afterwards you will stop in Poggibonsi for a break and lunch in a beautiful wine cellar. 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 sensation of being immersed in a film set. Not for nothing is it considered one of the most beautiful villages in Tuscany. Enjoy some free time to wander around its beautiful medieval streets, admire gems such as the Piazza della Cisterna or the 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 photo taken holding the Leaning Tower of Pisa. It's a tradition that every traveller must do in Italy.

What's included in this tour

Itinerary

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 as it is not always possible to take in everything you would like to. So, if you have limited time during your trip to Florence to take a tour of 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 towns and explore the beautiful Tuscan countryside with the advantages of travelling 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 get to know first-hand everything you want to know about the main places of interest, but you will also have free time to customise your excursion 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 visit.

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 great, 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 all the photos and videos of the excursion to your social networks, 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'll have to get up early, but even if it's tempting, I don't advise you to take a nap on the bus because on the way you'll see a beautiful rural landscape of hills and vineyards, a prelude to the "gothic dream" that is this World Heritage city.

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

At the end and before having lunch in an old typical Tuscan wine cellar, you will have time to see the fortress of Monteriggioni, a little 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 you to go 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

Itinerary

Although it may not have the fame of other Italian cities such as 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. There is a reason why it was declared a World Heritage Site by UNESCO.

The village can be easily covered in a couple of hours because it is not very big and it is especially known for its landscape of stone towers, so high that they 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 there were during the Middle Ages, 14 remain today, and you can even climb some of them to contemplate the views of the surrounding area. I recommend this to admire from the sky both the magnificent architecture of San Gimignano and the beautiful landscape of cypress trees, vineyards and olive groves 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 to 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 lookout point over 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 sensation of taking a trip back in time to the past, as it still preserves that beautiful medieval atmosphere that transports you to another era and captivates you.

If during your trip to Florence you would like to do several excursions to get to know the surroundings of the city, I recommend 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 your holiday 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-see places in the city such as the Duomo, the Uffizi Gallery or the Accademia Gallery, among many other emblematic places.