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San Gimignano Wine 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 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.

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.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

3. 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.

San Gimignano: Truffle Hunting with Lunch & Wine Tasting

4. 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. Tour the Tenuta Torciano Winery before settling in for a tasting of local wines. Start with a tour of the Tenuta Torciano Winery before getting a brief lesson on truffle hunting. 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. For lunch, dig into Tuscan cheeses and cold cuts, bruschetta, tagliolini with truffle and truffle lasagna, roasted meat with a vegetable side dish, and cantuccini cookies for dessert. Taste renowned local wines like Vernaccia di San Gimignano, Chianti Classico, Brunello di Montalcino, and more. Learn about the wines and local industry from the local sommelier.

Half-Day Horseback Riding in Tuscany and Lunch in Winery

5. Half-Day Horseback Riding in Tuscany and Lunch in Winery

On horseback is an excellent way to explore the trails and byways of Tuscany, taking in vineyards and olive groves at a relaxed pace against a backdrop of rolling green hills and landscapes. Once arrived, our guide will match you with a horse that fits your level and needs. The horses are very reliable and also persons without riding experience can partecipate on this tour. We ride through lush vineyards, native woods, olive groves and rolling hills to offer you a collection of breathtaking and unforgettable views. Find the right rhythm and get in harmony with your horse, immerse yourself in the fresh and clean air of the countryside and walk along the newly cultivated fields among patches of sunflowers. After the ride, we will stop in Tenuta Torciano winery to enjoy an authentic Tuscan lunch with typical appetizers (bruschetta, pecorino cheese, cold cuts), lasagna with meat ragù, roasted meat and cantuccini biscuits as dessert. All this will be nicely combined to a great wine tasting class in which you will have the pleasure to taste wines of local production: Vernaccia di San Gimignano, Chianti, Chianti Classico and many other Super Tuscans. You will have the chance to take amazing pictures of the magnificent landscape offered by the Chianti region. And after the tasting if you like you will have the opportunity to buy or ship home. Lunch includes: • Appetizers: Tuscan cheeses and cold cuts, bruschetta • First course: lasagna with meat ragù or ribollita Tuscan soup • Second course: roasted meat with vegetable side dish • Dessert: cantuccini biscuits with dessert wine

From Florence: Tuscany Wine Tasting Full-Day Trip

6. From Florence: Tuscany Wine Tasting 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 PM with an estimated travel time of 1 hour and 10 minutes. You'll arrive back in Florence at about 5 PM.

San Gimignano: Vineyard Walk & Lunch with Wine Tasting

7. San Gimignano: Vineyard Walk & Lunch with Wine Tasting

Visit a new Spiral vineyard, capable of producing mixing aesthetics and tradition, which has become a new attraction in Italy. A harmonious succession of rows of vines arranged in a spiral circle in a spaced move from an island in the central stone as vantage point to enjoy this spectacle of nature.  Visit the estate with a guide with whom you will trace the historical roots to the current production line. During the visit of about 1.5-2 hours, you will have the opportunity to taste wines of the estate's production.  The visit is aimed at a broad audience of both wine lovers and people who wish to make a first wine culture experience. LUNCH MENU Appetizers: Tuscan cheeses and salami, Bruschetta and snack. First Course: Truffle lasagna and tuscan ribollita Second Course: Roast meat with roast potatoes Dessert: Cantuccini with dessert wine WINES 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 flavored Olive Oil Pepper Hot Olive Oil Balsamic Old Vinegar selected

San Gimignano & Siena: Small Group Wine Tour from Rome

8. San Gimignano & Siena: Small Group Wine Tour from Rome

Travel through Italy on a full-day journey from Rome, through the hills of Chianti, to the cities of San Gimignano and Siena. Arriving in San Gimignano, a UNESCO World Heritage Site, explore its charming medieval streets and sample the world-famous Vernaccia white wine.  Stop for a wine tasting and sample local products in a beautiful wine cellar: 10 different types of wine and oil. Then visit the estate and learn about the processing of the grapes before having lunch at a restauarant.  Finally, make your way to Siena for a lovely wander around the historic center of the city, a well-deserved UNESCO World Heritage Site. Walk along Piazza del Campo, the public square that's also home to the Palio di Siena horse race. Visit the Mangia Tower, and admire the Duomo's Romanesque-Gothic facade, before beginning the trip back to Rome through the Tuscan countryside.

San Gimignano: Private Vineyard Lunch and Wine Tasting Tour

9. San Gimignano: Private Vineyard Lunch and Wine Tasting Tour

Discover the best of the Chianti region from its history and landscapes to its wine and culinary traditions during this private winery tour, guided tasting, and 4-course meal experience at Tenuta Torciano in San Gimignano. Spend the day immersed in the countryside atmosphere. Start your visit with a meal right inside the vineyards will give you the chance to immerse yourself in nature and live an experience of the senses, soaking up the air, the colors, the flavors, and the smells of the countryside. Enjoy coziness and the gentle sounds of the earth as you taste menu items such as Tuscan cold cuts, cheeses, lasagna, soup, roasted meat, fresh seasonal vegetables from the garden, and more. During lunch, enjoy the famous Vernaccia white wine, Chianti Classico, Brunello di Montalcino, and many other renowned Tuscan wines paired with extra virgin olive oil. Meet your private wine expert who will guide you through your tasting and share secrets of wine and oil production. The rural yet elegant setting of the estate will perfectly frame and complete your experience. Lunch Menu: • Appetizers: Tuscan cheeses, cold cuts, and bruschetta • First course: lasagna with meat ragù or ribollita Tuscan soup • Second course: roasted meat with a vegetable side dish • Dessert: cantuccini, biscuits, and dessert wine

Florence: Siena, San Gimignano & Chianti Day Trip with Lunch

10. Florence: Siena, San Gimignano & Chianti Day Trip with Lunch

Hop aboard your minibus at 7:45 AM and drive for around an hour through the Tuscan countryside. Enter the heart of Siena, and start the visit with your guide. Take off through the town's narrow streets and hear stories about Siena as you go. Skip the 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. After your walking tour, enjoy some free time to enjoy Siena at your own leisure. Move on to San Gimignano, and admire the unique Tuscan landscape as you drive through marvelous scenery surrounded by olive trees, vines and old stone buildings on your way. Stop at a family owned wine estate to relax and enjoy a traditional Tuscan lunch for a taste of country hospitality. After lunch, take an easy drive to San Gimignano to finish your day. Famous for its splendid skyline of tall medieval towers, have free time to explore on your own. Discover the main street full of typical shops, have a look at the Collegiata (main church), or enjoy a gelato. Return to Florence in the late afternoon.

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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