San Gimignano
Wine Tasting & Winery Tours

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Our most recommended San Gimignano Wine Tasting & Winery 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: Tuscany Wine Tasting Full-Day Trip

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

6. 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

7. 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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San Gimignano Area: Wine Tasting Experience

8. San Gimignano Area: Wine Tasting Experience

A few steps from San Gimignano, there is a splendid family-run winery. Here, you can taste typical Tuscan products including wine and tasty local croutons. Do not miss the opportunity to learn how to combine Tuscan wine with appetizing foods and find out how wines are produced in a real cellar. You will visit the cellar, the vineyards, and all the places where the wine comes to life. Listen to stories, and hear about winemaking processes. You'll discover that Tuscany and Chianti are areas to be loved and protected. As you discover the secrets of wine and grapes, you'll also learn about the best food pairings.  You can choose between two unique experiences:  Tasting of four wines accompanied by snacks of typical products preceded by a tour of the cellars and vineyard Lunch and tasting of four wines preceded by a tour of the cellar and the vines

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Florence: Chianti Villages, San Gimignano & Wine Roads

9. Florence: Chianti Villages, San Gimignano & Wine Roads

Journey into the heart of the Chianti region along the famous Chiantigiana Road and through a classic Tuscan landscape characterized by gently rolling hills, vineyards, silver olive groves and dotted with quaint villages. Near Greve in Chianti, enjoy a tour of a local winery with wine tasting. Here you have the opportunity to taste and buy organic extra virgin olive oil. En route, stops to get to know the area including the stunning UNESCO World Heritage Site of San Gimignano, famous for its 13 medieval towers which dominate the skyline. At the end of the visit to San Gimignano, enjoy a traditional Italian light lunch with a wine tasting, either in a wine estate or a typical restaurant producing organic wine. Throughout the day, you will travel in a comfortable car or minivan with an English-speaking driver. 

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From San Gimignano: Chianti by E-Bike with Wine Tasting

10. From San Gimignano: Chianti by E-Bike with Wine Tasting

There is no better way than by bicycle to discover the beauty and richness of this part of Italy, sharing in the passion for cycling, art, food and wine. The tour takes place in Tuscany, more specifically, in the magnificent landscapes surrounding Siena. There are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. From the seat of your electric bike, you will discover how Tuscany life flow slowly yet incessantly, creating a natural equilibrium among art, culture, and nature. Tuscany is paradise for a cycling tourist, who will be greeted by gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between fields of sunflowers and vineyards, and is punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gimignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to the splendid medieval for tress of Monteriggioni. 

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Other Sightseeing Options in San Gimignano

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What people are saying about San Gimignano

Overall rating

4.6 / 5

based on 4,582 reviews

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!

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.

Great group experience, enough time to walk around and enjoy. Would have liked more time at Pisa, maybe Pisa should be a bit longer, just a suggestion.

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.

The guide was perfect Our guide Lavina was so helpful and understanding ❤️