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53 results
Visit two Tuscan wineries without having to worry about designating a driver by opting for this tour that includes transportation. Immerse yourself in the Chianti wine region as you sample a variety of wines. Discover the art of winemaking through tastings while enjoying the scenery of the Tuscan countryside. Then head to San Gimignano to spend some time exploring its medieval ramparts.
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Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
6 hours
Free Cancellation
4.8
(69)
from
$95
Experience the beauty of Tuscany aboard a vintage Fiat 500 as you explore the scenic Chianti countryside. Travel through rolling hills, vineyards, olive groves, and charming medieval villages in a convoy of classic Fiat 500s driven by professional drivers. Along the way, stop at panoramic viewpoints and visit local wineries for guided tastings of Chianti wines, extra virgin olive oil, and balsamic vinegar. Enjoy a traditional Tuscan lunch at a winery, featuring local specialties and regional wines. Throughout the day, your tour leader will share stories and insights into Tuscan culture, making this a unique, authentic, and unforgettable Tuscan experience.
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Fiat 500 Tour in Chianti with Private Driver,Lunch & Wine Tasting
7 hours
Free Cancellation
4.5
(7,005 Operators)
from
$210
Special Offer
Discover the authentic beauty of Tuscany on an unforgettable scooter adventure through the famous Chianti hills. Ride along scenic roads surrounded by vineyards, olive groves, cypress trees, and medieval villages while experiencing the true essence of Tuscany. After a safety briefing and driving test, follow your local guide through panoramic routes and hidden corners of the countryside, stopping at breathtaking viewpoints and learning about Chianti wine culture and local traditions. Visit local wineries to enjoy tastings of Chianti wines, extra virgin olive oil, and balsamic vinegar. Savor a traditional Tuscan lunch in a charming vineyard setting, featuring bruschetta, cold cuts, cheeses, handmade pasta, and regional wines. Continue your scenic ride through the rolling Tuscan hills before returning to the starting point. Perfect for travelers seeking a unique blend of adventure, wine, food, and spectacular scenery.
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Chianti Scenic Drive with Wine Tastings & Tuscan Lunch
7 hours
4.5
(7,007 Operators)
from
$158
$147
Likely to Sell Out
Discover the magnificent architecture of the Renaissance on this full-day tour from Florence to Pisa and Lucca. Explore the famous marble monuments of Pisa’s Piazza dei Miracoli with a guide, including the city’s grand cathedral and vaulted cemetery. For the ultimate Pisa experience, climb the famous leaning tower and soak up panoramic views. After a stop at a local vintner’s shop for wine tasting, continue on to the medieval walled city of Lucca, where you’ll enjoy free time to stroll the well-preserved streets and squares your own.
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From San Gimignano: Pisa Half Day Trip
6 hours
Free Cancellation
4.2
(6)
from
$57
Beautiful tour that will take you to discover the medieval town of San Gimignano. Not only its towers, but 1000 stories of pilgrims, merchants, travelers who made this place a very rich medieval destination. Churches, squares, alleys, and fantastic views. Join us to find out what tourists on their own often lose the beauty of Sa Gimignano
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Visit of San Gimignano with local expert guide
1 hour 30 minutes
Free Cancellation
3.8
(10)
from
$23
Likely to Sell Out
See Tuscany in classic Italian style by exploring the bucolic region in a vintage Fiat 500. Take the wheel of the classic Italian automobile then ride to the stunning hilltop town of Monteriggioni, cruise through the rolling hills of Chianti, and stop at a local vineyard for a hearty lunch of local fare.
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Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti
7 hours
Free Cancellation
4.3
(52)
from
$210
Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 2-Days 5-Cities Flexible Sightseeing bus tour
2 days
Free Cancellation
4.5
(4)
from
$88
Discover the sights and flavors of Tuscany by e-bike on a private Chianti cycling tour. Meet your cycling guide directly at the starting point or choose pickup at your San Gimignano hotel. Then set off along quiet roads and trails, the perfect way to immerse yourself in the region’s world-famous landscape. Pedal your way to a traditional family farm and wine cellar. There you enjoy a filling meal featuring local specialties and paired with the estate's own wines.
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Private E-bike Tour in Chianti from San Gimignano
6 hours
Free Cancellation
4.8
(4)
from
$445
Price varies by group size
San Gimignano, with its rural, hillside atmosphere, is a great place to sample Tuscan food and wine. This tour pairs Tuscan wine tasting with an elaborate Truffle-based meal at a family-run olive farm and vineyard. The meal is led by one of the farmers, who explains the characteristics of the wines and their organic production. The farm is within walking distance from the center of San Gimignano, so you can walk right over.
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Private wine, Extra Virgin Olive Oils & Cheese Tasting
45 minutes
Free Cancellation
4.1
(12)
from
$64
This exclusive truffle adventure sets itself apart by combining the thrill of truffle hunting with a hands-on Tuscan cooking class, offering a genuine farm-to-table experience in an intimate setting. Guided by a knowledgeable truffle guide, chef, and sommelier, you’ll explore the woods close to our farm ( 5/10 minutes driving from the meeting point), uncovering the secrets of truffle cultivation before heading into our rustic kitchen. Here, you'll master the art of fresh handmade pasta, craft delicious bruschetta, and prepare delicious truffle-infused dishes, all using authentic local ingredients. What makes this experience truly unique? The personalized attention, immersive cultural connection, expertly paired organic wines, and e.v.o. Olive oils and balsamic vinegar complement every dish. More than just a class, this is a luxurious, hands-on journey into the heart of Tuscan flavors—an unforgettable experience for truffle lovers and food enthusiasts alike! ✨
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Truffle Hunting & Truffle Cooking Class
4 hours 30 minutes
Free Cancellation
4.8
(4)
from
$356
A special tour that gives more space to the natural environments surrounding the farm. You will be taken on a walk through the fields and vineyards and linger in the shade of a large oak tree for a cool Aperitivo. The tour continues through the vinsantaia, historical cellar, collection of agricultural tools. Tasting of 8 wines from our production: - "Casa Lucii" DOCG Vernaccia di San Gimignano; - 2 different vintages of "Mareterra" DOCG Vernaccia di San Gimignano reserve; - "Spicchio" IGT rosé Tuscan; - "Fuscelli" DOCG Chianti; - "Senarum" DOCG Chianti Colli Senesi; - "Arturo" IGT Tuscan Red with tailor-made artisanal chocolate pralines; - "Curato" DOC Vin Santo del Chianti with Tuscan Cantuccini. The tasting is accompanied by a taste of our organic extra virgin olive oil, cheese and cold cuts selection produced by local farms and accompanied by vegetables from the garden.
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Tasting with welcome Aperitivo in the vineyard of organic wines
4 hours
Free Cancellation
5.0
(1)
from
$140
Navigate through the picturesque landscapes of Tuscany with the Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 5-Days 5 Cities Flexible Sightseeing bus tour
5 days
Free Cancellation
4.5
(5 Operators)
from
$108
During an e-bike tour in Certaldo, you will experience a perfect blend of medieval history, breathtaking landscapes, and authentic Tuscan culture. This area is ideal for cycling, thanks to its rolling hills, scenic country roads, and charming historic center. Certaldo Alto – The Medieval Heart One of the highlights of the tour is reaching Certaldo Alto, the beautifully preserved hilltop medieval village. Here you can explore: Narrow brick-paved streets, ancient walls, and historic gateways Palazzo Pretorio, the symbol of medieval civic power, decorated with coats of arms and frescoed rooms The House of Giovanni Boccaccio, birthplace and home of the famous author of The Decameron Historic churches such as Saints Jacopo and Filippo, where Boccaccio is buried From the village, you’ll enjoy stunning panoramic views over the Val d’Elsa countryside. Tuscan Countryside Riding Outside the town, the route continues through classic Tuscan scenery: Vineyards, olive groves,
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Certaldo E Bike Tour
3 hours
Free Cancellation
from
$117
The contact with nature and with truffle dogs makes it a unique experience of its kind. It is very fun and special.
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Truffle hunting
1 hour 30 minutes
Free Cancellation
4.0
(4)
from
$105
This is a one of a kind treasure hunt. It takes place in a real medieval historic building, mostly decorated with coats of arms that belonged to the noble Florentine families. Ideal for a group of friends who want to spend a different day than usual, for corporate team building activities but also for a family with teenagers. The puzzles are fun and will stimulate your imagination. The palace in which the hunt takes place is simply magical.
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Treasure hunt of the Vicar
1 hour
Free Cancellation
from
$29
Bus tours can make many stops in a short amount of time, but they can be plodding affairs and leave travelers feeling out of touch with the landscapes they drive through. This tour—which takes to the roads of the Chianti region on vintage Fiat 500s—allows visitors more fun and the chance to drive themselves while they follow a guide. Pass medieval villages, rolling countryside, and wineries, and stop for a Tuscan lunch and wine tasting.
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500 Vintage Tour - Chianti wine tour - Small group
7 hours
Free Cancellation
5.0
(6)
from
$210
Indulge in a private truffle-based lunch in an authentic Tuscan setting at a family-run biodynamic farm near San Gimignano. Begin with an introduction to the farm’s sustainable agricultural methods, learning about biodynamic winemaking and olive oil production. Then, savor a carefully curated meal featuring truffle-infused dishes, paired with organic wines and extra virgin olive oils produced on-site.
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Private Wine & Evo oil tasting with Truffle Meal
1 hour 30 minutes to 2 hours
Free Cancellation
4.2
(5)
from
$99
Discover the most beautiful places of San Gimignano and the surrounding Chianti area starting from Florence with our professional photographer and our guide who will take you wonderful photos in the village and on the hills among the vineyards. You will not be a passive spectator, but you will be the center of attention, free to enjoy the experience without hindrances such as cameras and various devices. Once the tour is over the photographic material will be shared telematically already edited.
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Private tour San Gimignano-Chianti w/ photographer from Florence
6 hours
Free Cancellation
5.0
(11 Operators)
from
$350
Price varies by group size
On this wine-tasting tour, you will sample some of the region’s best prosecco, rosé, and a variety of Tuscan red wines. Every glass is perfectly paired with local cured meats, cheeses, and various homemade pasta dishes (please inform us if you have any dietary restrictions). As you make your way through the villa’s multiple tasting rooms, you will discover that the Corbucci Wine Boutique not only produces excellent wine, they also make several other exceptional products, including limoncello, grappa, olive oil, and balsamic vinegar. All products are made from the finest, local ingredients and crafted with expert care. All good things must come to an end, and so must this tour. But there is no better way to conclude a wine-tasting experience than with a little more wine. To finish what promises to be an already wonderful experience, your gracious hosts will invite you to join them in raising a glass of Vin Santo—a traditional Tuscan dessert wine—to send you off with a sweet goodbye.
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Wine Tasting In A Beautiful Tuscan Villa
3 to 8 hours
Free Cancellation
from
$117
Price varies by group size
This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in the cellar, to get to know the viticulture and winemaking techniques
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San Gimignano: Vineyard and Cellar Tour with Wine Tasting
1 hour 30 minutes
Free Cancellation
5.0
(3)
from
$53
Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 3-Days 5-Cities Flexible Sightseeing bus tour
3 days
Free Cancellation
4.5
(5 Operators)
from
$98
This experience uniquely combines the ancient art of falconry with Tuscany’s rich culinary traditions, all in the stunning setting of Podere La Marronaia. What makes this experience special? - Interactive falconry session: Watch hawks, falcons, and owls in flight and even hold a bird of prey. - Expert-guided insights: Learn about the history and techniques of falconry from skilled falconers. - Authentic Tuscan Merenda Break: Enjoy a tasting of organic wines, extra virgin olive oils, and balsamic vinegars paired with bruschetta, cheeses, and cured meats. - Breathtaking countryside setting: Admire panoramic views of the Tuscan hills and San Gimignano’s medieval towers. A perfect blend of nature, history, and gastronomy, offering an unforgettable Tuscan experience.
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Wine and Falconry activities in San Gimignano
2 hours
Free Cancellation
5.0
(968 Operators)
from
$234
Tuscany is Italy’s gastronomic heartland and a cooking class is the perfect way to discover the region’s rich culinary traditions. On this 3-hour small-group cooking class, pick up tips and techniques from a local chef; create traditional recipes such as antipasti, bruschetta, and pasta dishes; then enjoy a homemade meal, accompanied by Tuscan wines.
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3-hour Tuscan Cooking Class with Wine & Oil Tasting
3 hours
Free Cancellation
4.7
(38)
from
$222
Tuscany is Italy’s gastronomic heart and this full-day tour from San Gimignano is the ideal introduction for traveling foodies. Sample regional wines and Tuscan specialties at a Montalcino winery; enjoy a self-guided tour of Montalcino fortress; taste regional delicacies such as Pecorino cheese in Pienza; and discover the famous Nobile di Montepulciano wine at a Montepulciano winery.
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Chianti & Montalcino Wine Tour from San Gimignano
8 hours
Free Cancellation
4.3
(6)
from
$163
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