San Gimignano
Sightseeing Tours

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Our most recommended San Gimignano Sightseeing Tours

From Florence: Siena, San Gimignano & Monteriggioni Tour

1. From Florence: Siena, San Gimignano & Monteriggioni Tour

Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT Coach. Arrive at San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the landscape. Make the second stop at Siena. Explore the Piazza del Campo, famous for the Palio Horse Race and for its splendid examples of Gothic civic architecture. You can also visit the magnificent Palazzo Pubblico. Finally, visit Monteriggioni and its intact medieval city walls. Then, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

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From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

2. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

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.

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From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-Day Trip with Lunch

3. From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-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.

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From Florence: Tuscany Day Trip with Optional Lunch and Wine

4. 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.

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

5. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Lunch

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. 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. You will then return to Florence.

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From Florence: Tuscany Wine Tasting Full-Day Trip

6. From Florence: Tuscany Wine Tasting Full-Day Trip

Join this fun day-trip made for 18 to 35-year-old travelers to the Chianti countryside by van, and discover why the area is famous for its scenery as well as its wine. Visit two local wineries and taste their flavorful wines, as well as local produce samples. Walk through the streets of San Gimignano at your own pace, discovering this charming town first-hand. Head straight to a wine tasting school, your first stop, where you will taste 4 different type of wines, including the famous Chianti Classico D.O.C.G. and a Super Tuscan wine, a 30 year-old balsamic vinegar, and the delicious truffle extra virgin olive oil. Here, learn how to recognize the different flavors and develop your taste buds together with a wine passionate producer. Next, drive to your second stop, a local winery located in a stunning area well-known for the production of the D.O.C.G. Vernaccia white wine and facing the famous towers of San Gimignano. Let the winemakers guide you through the vineyards and the cellars and they will share the secrets of the wine and oil production as well as the best wine and food combinations. At this winery, take the opportunity to buy their local products and wine at a convenient cost to bring back home or to ship to friends and family. In the afternoon, enjoy visiting and spending time wandering through the narrow streets of San Gimignano at your own pace. Shop 'til you drop and enjoy gelato from the world-champion ice-cream making gelateria. Your departure from San Gimignano is at 3:45 PM with an estimated travel time of 1 hour and 10 minutes. You'll arrive back in Florence at about 5 PM.

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Horseback Riding from Siena

7. Horseback Riding from Siena

An old riding school situated in a tranquil and peaceful area of Castellina in Chianti immersed between the rolling hills of the Tuscan countryside. After a short journey on a private air-conditioned minivan, the horses will be there waiting for you. Don’t worry if you haven’t ridden a horse before, the experienced staff will make sure you feel confident before leaving for a ride. You will ride through lush vineyards, native woods, olive groves and rolling hills for a collection of breath taking and unforgettable views.

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From Florence: Siena, San Gimignano and Chianti Wine Tasting Full-Day Trip with Lunch

8. From Florence: Siena, San Gimignano and Chianti Wine Tasting Full-Day Trip with Lunch

Enjoy a wonderful day in the Tuscan countryside, visiting the most gorgeous corners of Siena, San Gimignano, and the Chianti area. Departing from Florence, drive to the historic village of Monteriggioni. Admire the landscape of olive groves and vineyards dotted with Romanesque churches, farmhouses, villas, and castles. Continue to Siena, where a local expert guide will lead you through the city's steep medieval streets to marvel at splendid palaces. Reach the Cathedral, Palazzo Comunale, and Piazza del Campo, where the Palio race takes place every year. Make a stop at a farmhouse in Chianti, where you will taste some of the best Tuscan wines, and a tasty lunch made with local produce. Continue to San Gimignano, declared a World Heritage Site by UNESCO. The guide will lead you into the heart of the village and then you will have free time to discover the beautiful squares, buildings, and alleyways.

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San Gimignano, Siena, Chianti Guided Tour from Florence

9. San Gimignano, Siena, Chianti Guided Tour from Florence

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.

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Full-Day Excursion to Siena, San Gimignano & Chianti

10. Full-Day Excursion to Siena, San Gimignano & Chianti

Enjoy a full-day excursion by minivan to see the beautiful Chianti area and to visit the cities of Siena and San Gimignano.  Depart at 9:00 AM from Piazza Cavalleggeri, the meeting point located in the city center of Florence. Stop at Piazzale Michelangelo for few minutes to see the splendid panorama and then in one hour you will arrive in Siena. Take a guided tour of the city center, including Piazza del Campo and the Cathedral. There is free time to walk by yourself in the narrow and ancient streets.  Then leave Siena to arrive in Monteriggioni, an old Medieval little village. After a short stop, continue to San Gimignano where you will have free time to explore the city center on your own. San Gimignano is famous for its towers, vernaccia wine and its characteristic craft articles.

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Other Sightseeing Options in San Gimignano

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What people are saying about San Gimignano

Overall rating

4.4 / 5

based on 3,501 reviews

This was an excellent and affordable trip to 3 places throughout Tuscany. When I priced the train to Pisa and back, it was approximately the same cost as this trip. Our tour guide was excellent, the winery that we stopped at was very good and the host was exceedingly entertaining. I do wish we had had more time in Sienna as it was beautiful, but I understand there is a time constraint. Overall, I would highly recommend this tour.

Great trip to see a lot in a relative short time. Tuscan country side, Old towns and good food. Our guide Manolo was great, with a lot of information about Tuscany and Florence and on the way back he went past everyone to answer any questions they might had. Loved it!

Valentina was a very good guide providing all the necessary information for our day tour! We also had a very profesional driver (Raul) The tour is totally recomended! Get the one with the entrance in the Siena included! Thanks you for the beautiful experience!

Amazing immersion in the Italian history, art and cuisine. Perfect combination of sight seeing in 3 "must see" places in Tuscany, complete taste of the incredible food and wine from Tuscany and enjoyable and entertaining guide with Alessandro.

Very nice trip! Saw all the sights without worrying about where to go and how to get there. Would book if you get tired of having to plan out your day.