Things to do in San Gimignano

Our most recommended things to do in San Gimignano

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

2. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch

Discover UNESCO World Heritage Sites and taste Chianti wines on a full-day trip from Florence. Visit Pisa, San Gimignano, and Siena, and savor a traditional Tuscan lunch.  First, head to Pisa to marvel at the Piazza dei Miracoli, Pisa Baptistery, Pisa Cathedral, and, of course, the famous Leaning Tower of Pisa. Continue to a wine villa in the Chianti countryside. Enjoy a tour of the estate and learn about its history in the medieval chapel before your first tasting of Chianti Classico on the panoramic terrace. Next, relish a typical lunch accompanied by two of the estate's products, a "Riserva" and an IGP wine. After lunch, relax a while in the villa's luscious gardens before going to the medieval town of San Gimignano.  Then, follow the scenic roads to Siena for a tour of the city's monuments and piazzas. Visit Piazza del Campo — the site of the Palio di Siena horse race — and admire the cathedral's exterior in Piazza del Duomo. After some free time, return to Florence.

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

3. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and opt for a guided tour in your preferred language to learn even more about the historic area. Begin with the visit at Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. After some free time in Siena you'll have lunch in a typical Tuscan winery. Then go ahead to the vineyard, where you can enjoy some local wine and visit San Gimignano, a UNESCO-listed medieval town. Continue to Pisa and to visit its stunning Piazza dei Miracoli. Admire the Baptistery, the cathedral, and, of course, the famous leaning tower.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Guided Tour

4. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Guided Tour

Experience the best of Tuscany on a day trip from Florence. Visit the Leaning Tower of Pisa, the hilltop town of San Gimignano. Journey into the heart of the Chianti region for wine tasting and lunch. Start your tour in Pisa and marvel at the celebrated Leaning Tower. Explore the grounds and see the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Continue to a winery in the foothills of San Gimignano and enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside. Continue to Siena, where a specialist guide will lead you on a walk through the city's historical center. Admire the exterior of the magnificent cathedral, and pass through the shell-shaped Piazza del Campo, where the Palio horse race is held twice a year.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

5. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares, and many local craft stores. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

6. From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell-shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

7. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art.  Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day.  Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo.  Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race.  The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.  If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

San Gimignano: Tuscany Truffle Hunting with Wine and Lunch

8. San Gimignano: Tuscany Truffle Hunting with Wine and Lunch

Have you ever wanted to try your hand at authentic truffle hunting with the help of beautiful dogs? Then this is an experience not to be missed. After meeting your professional guide, have a lesson to learn all about how to recognise and search for truffles, with the help of an English-speaking translator.  After building up your confidence with your lesson, set off on a truffle hunt with beautiful dogs, searching through stunning oak forests. Following an exciting truffle hunt, sit back, relax and savor a delicious lunch made with Tuscan products. Sample some of the winery's finest wines to complete your experience.  LUNCH MENU: Appetizers: Tuscan salami and cheeses, Bruschetta (Bread with Olive Oil), and snack. First Course: Truffle lasagna with meat sauce; Second Course: Roasted meat with potatoes and vegetables; Dessert: Cantuccini with Dessert Wine;                                                                                                          WINES AVAILABLE FOR TASTING: Brunello di Montalcino D.O.C.G. Cabernet Bartolomeo Riserva I.G.T. Merlot Baldassarre Riserva I.G.T. Syrah Cavaliere Riserva I.G.T. Vernaccia of San Gimignano D.O.C.G. Chianti D.O.C.G. Chianti Classico D.O.C.G. Chianti Classico Riserva D.O.C.G. Vino Nobile of Montepulciano D.O.C.G. Red of Montepulciano D.O.C. VinBeato - Dessert Wine Extra Virgin Olive Oil Cold Pressing White Truffle flavoured Olive Oil Pepper Hot Olive Oil Balsamic Old Vinegar selected

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

9. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

From San Gimignano: Horseback Riding in Tuscany

10. From San Gimignano: Horseback Riding in Tuscany

You will be brought to an old riding school in a private, air-conditioned minivan. Soak-up the atmosphere of the old riding school situated in a tranquil and peaceful area nestled between the rolling hills of the Tuscan countryside. The horses will be there waiting for you. Don’t worry if you haven’t ridden a horse before, the experienced school staff will make sure you feel confident before the ride commences. They will help you to become familiar with the horse, showing you all the necessary techniques to ride. You will ride through lush vineyards, native woods, olive groves and rolling hills for a collection of breathtaking and unforgettable views.

Top sights in San Gimignano

Frequently asked questions about San Gimignano

What top attractions are a must-see in San Gimignano?

The must-see attractions in San Gimignano are:

What are the best inexpensive tours in San Gimignano?

What are the best deals and discounts on activities and attractions in San Gimignano?

Other Sightseeing Options in San Gimignano

Want to discover all there is to do in San Gimignano? Click here for a full list.

What people are saying about San Gimignano

Overall rating

4.5 / 5

based on 10,359 reviews

The first winery was no i out t so good. Even if it is small then the place could be cleaner and neater. The second one Casa Emma is wonderful. Scenery is what we wanted to see and it’s there. The wines are good and cold cuts satisfying. The crown of the tour is the third one Poggio Torselli. The gardens is beautiful and small castle is restored wonderfully.

Fabulous driver/guide who could speak multiple languages really well and had deep local knowledge (including winemaking processes), lovely comfortable vehicle to travel in, stunning scenery, the right amount of time in each town and wine tasting with genuine local authentic quality wine makers (plus lovely food). We highly recommend this trip!

Trip was amazing, To me that’s this is a must!! Communication with staff was great, bus was comfortable and the three places were wonderful, bring comfortable shoes cus you have to walk a lot.

Excellent choices of attractions and lunch. Be prepared for alot of walking and a long day....12hours+

Very well organised and personalised tour … mr steffano our guide was exceptional