3 Best 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, cuisine and landscapes truly fascinate travellers, it is Tuscany.

Take advantage of a getaway to Florence to explore some of Tuscany's most iconic destinations, such as Pisa, Siena, Chianti and San Gimignano, on a day trip by bus.

A road trip through Tuscany is one of the most romantic experiences you can have in Italy. This is a land of green meadows, rolling hills and vineyards stretching in every direction, charming little villages and delicious cuisine that will make you sigh with delight.

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 comprehensive you can take, because for a very reasonable price, not only will you visit some of the region's greatest gems (Siena, San Gimignano and Chianti) in one day, but you will also have the opportunity to enjoy a delicious traditional lunch and a tasting of regional wine and olive oil at a beautiful Chianti winery.

Why I like this tour

One of the advantages of Florence's geographical location is that you can visit some of Italy's most charming towns and cities in the surrounding area. Tuscany is home to real gems hidden among the hills, brimming with art and culture, which every traveller should enjoy at least once in their lifetime (although I warn you, this region is addictive!).

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 beautiful Tuscany at a reasonable price, and you won't have to worry about planning your travel or lunch along the way, as it is included. You'll save time and money that you can spend on other things, which is always a good thing!

In addition, when it comes to visiting the tourist attractions that are part of this tour, it combines 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.

What to expect

You will leave Florence early in the morning (at 8:45 a.m.) to board the coach with your group, which will take you to these iconic Tuscan towns that played such an important role in the Middle Ages and the Renaissance. This region is a historical and artistic treasure trove!

Get ready to travel through bucolic fields 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), discover the fortress of Monteriggioni (one of the best-preserved medieval complexes in Italy, which has hardly changed since the 13th century), and visit the small village of Chianti to visit a winery where you will take part in a wine tasting and enjoy a lunch of regional specialities.

Finally, you will go to Siena, the medieval treasure of Tuscany and home to 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 impressive sites such 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 this tour includes

Itinerary

Medieval villages that captivate the soul, fertile valleys and landscapes covered with vineyards, colourful sunsets, cuisine that will take your breath away... Leaving Florence and choosing a destination from 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 practically impossible to take in.

Why 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 such as this day trip to Pisa, Siena and San Gimignano, which means you don't have to give anything up during your trip.

You'll travel through the green plains of Tuscany to Siena (the artistic pearl of Tuscany and a World Heritage Site), enjoy a delicious Tuscan lunch and wine tasting at a charming winery-restaurant in Poggibonsi, discover the medieval town of San Gimignano (famous for its striking 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 best way to discover its culture, traditions and all the essential sites of Tuscany, such as Siena, Pisa and San Gimignano, in a single day is by taking this excursion.

It's all advantages! You won't have to worry about organising your travel (as you'll travel comfortably from one place to another by coach) or stops for food 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 so that you can enjoy the experience to the fullest!

In addition, this tour combines a guided tour with free time in the different cities visited, which is a very interesting option to consider if you want to enjoy the advantages of both.

What to expect

At 7:45 a.m., you will leave Florence by bus for Siena, nicknamed the "Red City," where you will visit the historic centre and such notable monuments as the Duomo, Piazza del Campo, Fonte Gaia, and Palazzo Tolomei, among others, accompanied by a guide.

You will then stop in Poggibonsi for a break and lunch at a lovely winery. In addition to savouring typical Italian dishes, you will have the opportunity to participate in a Chianti wine tasting. A truly fantastic and enjoyable gastronomic experience!

The next stop on this excursion is San Gimignano, a medieval town located on top of a hill that has the best skyline in Tuscany. I am not exaggerating! Its spectacular medieval towers, which have stoically withstood the passage of time, are visible from the road.

During your walk through San Gimignano, you'll feel like you're immersed in a film set. Not surprisingly, it is considered one of the most beautiful villages in Tuscany. Enjoy your free time to lose yourself in 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.

What this tour includes

Itinerary

Tuscany is one of those places in Europe where everything is worth seeing. It has sublime landscapes of green meadows and vineyards, spectacular cuisine 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's not always possible to see everything you'd like to. Therefore, if you have limited time during your trip to Florence to tour this legendary Italian region, my advice is to take this private day trip to Siena and San Gimignano.

Why I like this excursion

On this tour, you will see the highlights of both towns and explore the beautiful Tuscan countryside with the advantages of travelling on a private excursion (just for you and your group) and having the assistance of a guide throughout.

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 personalise your excursion in San Gimignano and go at your own pace, losing yourself in its beautiful medieval streets and stopping wherever and whenever you want. It is a very interesting option to consider if you like to combine both types of visit and have a personalised experience.

In addition, you will enjoy lunch in an authentic Tuscan winery where you can savour the region's excellent wines, relax for a while chatting with the group and get a taste of that Italian "buona vita" 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 all your photos and videos from the excursion to your social media accounts. I can assure you that there will be plenty, because Tuscany is a fascinating land that inspires true passion.

What to expect

To make the most of the day, the excursion leaves Florence early (at 8 a.m.) and heads for Siena. You'll have to get up early, but although it may be tempting, I don't recommend taking a nap on the bus because along 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, you will feel as if time in Siena has stood still since the 13th century. It is an incredible city! During the guided walking tour of the historic centre, you will see important monuments such as Piazza del Campo and Fonte Gaia, the Duomo and Palazzo Tolomei, among others. Listen carefully to the stories about the Palio di Siena festival, because it is much more than just a horse race!

At the end of the tour, and before lunch in an old typical Tuscan wine cellar, 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, it is one of the most beautiful places on the tour. You won't get tired of taking photos!

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

Before returning to the bus that will take you to Florence, I recommend visiting the main street of San Gimignano, which is full of typical little shops where you can buy souvenirs or ice cream.

What this tour includes

Itinerary

Although it is not as famous as other Italian cities such as Florence, Pisa or Siena, in my opinion San Gimignano is one of the most beautiful towns in the country and one of the must-see places in Tuscany. It is not for nothing that it has been declared a World Heritage Site by UNESCO.

The village can be comfortably explored in a couple of hours as it is not very big and is especially known for its landscape of stone towers, which are so tall that they can be seen from the road before you even reach the village. They have a curious origin, as they arose from a kind of competition between the wealthy families of the area to prove which was the richest and most powerful.

Of the 72 towers that existed during the Middle Ages, 14 remain today, and you can even climb some of them to enjoy the views of the surrounding area. I recommend doing this to admire both the magnificent architecture of San Gimignano and the beautiful landscape of cypress trees, vineyards and olive groves that surround it.

In addition to its towers, as you stroll through its charming medieval streets, you will see other buildings such as the Duomo (which has some wonderful 14th-century frescoes), the Palazzo Comunale (home to the Civic Museum and the entrance to the Torre Grossa), the Church of San Agostino, Piazza della Cisterna and the Rocca di Montestaffoli, which serves as a viewpoint 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 especially recommend it because during your visit you will feel as if you have travelled back in time, as it still retains that beautiful medieval atmosphere that transports us to another era and captivates us.

If during your trip to Florence you would like to take several excursions to explore the city's surroundings, I recommend you take a look at the article The 10 best tours and excursions from Florence to find inspiration for your next getaway.

However, if you prefer to focus on the capital of Tuscany during your holiday 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 city's must-sees, such as the Duomo, the Uffizi Gallery and the Accademia Gallery, among many other iconic places.