Add dates

San GimignanoWine tasting & winery tours

Our most recommended San Gimignano Wine tasting & winery tours

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

1. 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 choose a guided tour in your language to learn even more about the historic area. Begin with Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the Cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa. After your free time in Pisa, head to a typical Tuscan winery in the Chianti Area and enjoy a delicious lunch with some local wine. Explore the city of Siena and visit to 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. Enjoy your last stop in San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views.

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

2. 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.

San Gimignano: Lunch or Dinner at a Winery with Wine Tasting

3. San Gimignano: Lunch or Dinner at a Winery with Wine Tasting

Tenuta Torciano is just a few minutes away from the medieval village of San Gimignano, and enjoy a guided wine tasting woods and olive groves. Immerse yourself in the heart of the Chianti region and taste a delicious meal. Your wine expert will immerse you in the world of the wine. Then move to one of the beautiful tasting rooms and a typical lunch or dinner will be served along with local wine and olive oil tasting. Your expert local sommelier will guide you on a tour of Tuscany’s diverse wine producing regions, showcasing wines. Expect to leave with a deeper understanding of Italian wines and an educated palate.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

4. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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: Tuscany Wine Tour Full-Day Trip

5. From Florence: Tuscany Wine Tour Full-Day Trip

Join this fun day trip to the Chianti countryside by van. 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 to taste 4 different types of wines including the renowned black rooster Chianti Classico, Brunello of Montalcino, Super Tuscan wines, along with a 30-year-old balsamic vinegar, and truffle extra virgin olive oil. Develop your taste buds together with a wine producer. Move onto a local winery facing the famous towers of San Gimignano. Let the winemakers guide you through the vineyards and the cellars and share the secrets of wine and oil production. 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. Enjoy the Vernaccia white wine and a Chianti Colli Senesi D.O.C.G. 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 icecream making gelateria. Your departure from San Gimignano is at 3:45 PMn approx with an estimated travel time of 1 hour. You'll arrive back in Florence at about 5 PM.

Florence: Chianti Villages, San Gimignano & Wine Roads

6. 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. 

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

7. San Gimignano: Vineyard and Cellar Tour with Wine Tasting

Begin your wine tasting experience with a tour around the vineyards that surround the winery. While touring the vineyard, learn about the agronomic phases of the vineyard. Once you have toured the vineyard, you'll visit the wine cellar, where you’ll learn about the vinification process and aging techniques. Move into the tasting room, where you’ll get a chance to learn about wine and food pairing before starting your wine tasting. The wine tasting will include all the wines in the vineyard production. The wine tasting will be paired with local cured meats, cheese, and olive oil. Taste a variety of wines including, Vermentino IGT, Vernaccia di San Gimignano DOCG, Vernaccia di San Gimignano Riserva DOCG, Chianti DOCG, Chianti Riserva DOCG, Japigo, IGT Supertuscan, and Vin Ssanto del Chianti DOC.

Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

8. Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

Spend the day discovering many of the main highlights of the Tuscan countryside on this guided tour with a traditional Italian lunch included. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena. Your first stop will be Pisa and the Square of Miracles. See the cathedral, baptistery, and, of course, the famous Leaning Tower. The Leaning Tower is almost 56 meters tall, about 183 feet, and leans at about 4 degrees, making it one of the most famous and iconic buildings in the world.  From Pisa, drive past hilltop hamlets scattered across some of the most beautiful and enchanting areas of the countryside. Arrive at San Gimignano where a traditional Tuscan lunch with wine tasting will be served, if the option is selected. Continue to the preserved medieval village of San Gimignano, a UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous tall, narrow towers. Explore the town center and the charming craftsmen shops along the cobbled stone streets and small squares. End the tour in Siena, a hilltop town rich in art and traditions. Stroll the pedestrian historical center and visit the beautiful local cathedral. Take a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo. Sample Lunch Menu - Appetizer: cold cuts ( prosciutto, finocchiona, salami ) bruschetta olive oil and truffle oil pecorino cheese with balsamic vinegar and green salad - Main Course: penne with meat ragout and parmesan cheese - Dessert: homemade tart with jam and vinsanto - Tasting of 3 different wines

From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

9. From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

Start your experience in the morning and explore the scenic hills of the Chianti region where some of the most famous Tuscan wines are produced. Ride through the beautiful fields of vines, cypresses, and Tuscan rural houses. Enjoy plenty of stops for beautiful photo opportunities throughout your experience.  Stop at a local winery where the kind owners will escort you around their property before serving an authentic Tuscan meal, followed by wine and olive oil tasting. Hop on your scooter once again and follow your guide through the final part of the scenic ride, arriving back at the meeting point in the early afternoon.

San Gimignano: Truffle Hunting with Lunch & Wine Tasting

10. San Gimignano: Truffle Hunting with Lunch & Wine Tasting

Participate in a unique local Tuscan tradition with this guided truffle hunt followed by lunch and a wine and olive oil tasting. Follow the powerful noses of hunting dogs and learn how to discover precious truffles. Follow the trained dogs through the forest where precious black and white truffles are found. Learn to identify the different species of trees and the ideal habitat for truffle growth. Take a break in one of the winery’s tasting rooms for lunch and a tasting of local wine and olive oil. Taste renowned local wines and learn about the wines and local industry from the local sommelier.

Available activities

99 activities found
Sort by:
Page 1 of 7

Frequently asked questions about San Gimignano Wine tasting & winery tours

What are other things to do than Wine tasting & winery tours that are worth visiting in San Gimignano?

The other unmissable things to do in San Gimignano are:

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

4.6 / 5

based on 4,582 reviews

Stefono was an amazing tour guide: great knowledge of the area, just the right amount of wit, and he cared about us having a good experience! We also had a local guide in Sienna, who was amazing in her own right. The lunch was absolutely delicious with a variety of wines, good food, and a great view! The whole day was a whirlwind and left you ready for a nap on the drive back to Florence, but it was a fantastic experience well worth the price!

I got really excited! It was a beautiful sunny day in Tuscany. Not only the leaning tower, there is so much to discover and I was very surprised by Saint Gimigagno!

Alex was such an amazing tour guide. He was friendly and really made the experience the best of tuscany. the tour was beautiful and so informative

Everything was perfect, really enjoyed the tour. Beautiful Sienna I hope to be able to visit it again

Great day out. Really knowledgeable and engaging tour guide