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Visit a family-run winery in Chianti to experience the traditional side of local winemaking. With an included tasting of several house wines, this tour of Montefioralle Winery goes from Chianti classic to sweet vin santo. In warm weather, you can sample the wine in a scenic outdoor spot with views of the vines and the surrounding historic village.
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Montefioralle Winery - Tour and Wine Tasting in Chianti
1 hour 15 minutes
Free Cancellation
4.3
(99)
from
US$42
Discover Chianti Classico with a visit and tasting in Viticcio: explore the winery, discover the winemaking and taste our best wines. An authentic Chianti experience! Our experience takes place in a historic winery in the heart of Chianti Classico, where the Tuscan wine tradition is breathed in every detail. The location offers a breathtaking panoramic view of the surrounding hills, making each tasting an unforgettable moment immersed in the beauty of the landscape.
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In the Heart of Chianti Classico : Wine, Winery and Tradition
1 hour 30 minutes
Free Cancellation
5.0
(3)
from
US$40
Learn how to create up to three classic Italian dishes—including homemade pasta—during this private cooking workshop in Chianti. Head to a scenic countryside home for an intimate lesson led by a pair of local cooks. Workshops include a wine and olive oil tasting and home-cooked meal with vegetarian and vegan options available.
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Private Tuscan Cooking Class And Wine Tasting in Radda in Chianti
3 hours
Free Cancellation
5.0
(12)
from
US$166
What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, a family winery surrounded by the rolling hills of Montalcino. Guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the traditions, craftsmanship and passion behind Brunello di Montalcino production. The experience continues with a carefully curated tasting of premium Tuscan wines paired with a traditional Tuscan lunch featuring local specialities and fresh handmade pasta, creating a journey that combines wine, food and landscape in a truly authentic way. Far from crowded commercial tours, this immersive experience offers a refined and memorable taste of Tuscany in a relaxed and elegant setting. Each tasting is led by expert sommeliers, transforming every glass into a deeper journey through the world of Brunello di Montalcino.
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Montalcino: Brunello Wine Tasting & Tuscan Lunch
1 hour 30 minutes
Free Cancellation
5.0
(10)
from
US$117
Immerse yourself in the authentic culture of Chianti with a wine tasting in Radda, a medieval village nestled in the Tuscan hills. Surrounded by Sangiovese vineyards, this experience offers more than just a tasting—it’s a journey into local tradition. Guided by an expert, you’ll explore the full winemaking process, from fermentation to barrel aging, before sampling three typical Tuscan wines and a Vermouth. A perfect way to connect with the land, its history, and its flavors.
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Wine Tasting in an Authentic Tuscan Cellar in Radda in Chianti
1 hour
Free Cancellation
4.5
(81
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US$38
Enjoy Tuscany to the fullest on a private vineyard picnic. Discover our winery on a guided tour (optional), taste wine in a cozy atmosphere overlooking Montalcino, and enjoy your picnic basket filled with delicious homemade Tuscan specialties.
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Winery Tour & picnic in the vineyard with a bottle of wine
2 hours 30 minutes
Free Cancellation
4.7
(7)
from
US$48
Taste your way through Tuscany at a classic wine tasting. After a cinematic journey through a cypress avenue, a trained team will serve you 6 wines in 3 flights at your table. After an introduction to each wine, you will have the opportunity to taste the wines in detail by yourself.
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Classic Wine Tasting in Montalcino
45 minutes
Free Cancellation
4.8
(8)
from
US$36
Make the most of your time while in port in Livorno and avoid wasting hours trying to explore Tuscany by public transportation or rental car on this full-day private wine tour in the Chianti hills. Led by a wine-focused guide, take a scenic drive into the heart of the Chianti wine region and visit a local winery to learn about the winemaking process and sample local blends. Taste top-quality wine and Tuscan olive oil while admiring the rolling landscape before heading back to your cruise ship.
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Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
9 hours
Free Cancellation
5.0
(86)
from
US$546
Price varies by group size
Tour the cellars of Monterinaldi Castle with a sommelier as your guide. This historic castle in the heart of Chianti is the perfect setting to learn all about the winemaking process. After your private tour of the cellars, enjoy a 3-course Tuscan lunch with wine pairings in an 18th century villa.
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Radda in Chianti: Wine Tasting, Cellar Tour & Tuscan Lunch
2 hours
Free Cancellation
4.6
(10)
from
US$94
What makes this experience truly unique is the intimate atmosphere of Paradiso di Cacuci, a family winery nestled among the rolling hills of Montalcino, far from crowded commercial wine tours. Guests are welcomed into an authentic Tuscan estate where tradition, landscape and passion come together to create a genuine Brunello experience. From walking through the vineyards to exploring the ageing cellar, every moment offers a deeper connection to the craftsmanship and philosophy behind Brunello di Montalcino. The guided tasting allows travelers to discover the elegance and evolution of Sangiovese through carefully selected wines, perfectly paired with traditional Tuscan flavours. Surrounded by breathtaking vineyard views and the peaceful atmosphere of the Tuscan countryside, this experience is designed for those seeking not only a wine tasting, but a refined and memorable journey into the heart of Tuscany.
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Montalcino: Brunello Wine Tasting with Tuscan Specialities
1 hour
Free Cancellation
4.7
(7)
from
US$89
Discover Tuscany and biodynamic viticulture on a winery tour with a breathtaking view of Montalcino while you learn about our philosophy. During a seated wine tasting, we will serve you 6 different wines and give you a short introduction to each of them. Then you will have the possibility to taste them independently.
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Winery tour & wine tasting in Montalcino
1 hour 45 minutes
Free Cancellation
4.4
(43)
from
US$48
Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging in a guided tasting of three local wines, beautifully paired with a platter of Tuscan cured meats and cheeses. Discover the traditional methods and techniques used to produce high-quality wines. During the tasting, you’ll savor three exceptional wines, including the world-renowned Brunello and Rosso di Montalcino. Plus, you’ll have the unique opportunity to taste wine straight from the wooden barrel! Capture your memorable moments and feel free to share your experience on social media!
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Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese
1 hour 30 minutes
Free Cancellation
5.0
(7)
from
US$46
What makes this experience truly unique is the opportunity to discover the authentic soul of Montalcino through the intimate atmosphere of Paradiso di Cacuci, a family winery nestled in a small “corner of Paradise” among the rolling Tuscan hills. Far from crowded commercial tastings, guests are welcomed into a place where tradition, landscape and passion create a genuine Brunello experience. From walking through the vineyards to exploring the ageing cellar, every moment offers a deeper connection to the world of Brunello di Montalcino and the craftsmanship behind each bottle. The experience is enriched by breathtaking views, expert sommeliers, carefully selected wines and traditional Tuscan flavours, creating a refined journey into the heart of Tuscany. Whether you are a wine enthusiast or simply searching for an unforgettable moment in the Tuscan countryside, Paradiso di Cacuci offers a timeless experience shaped by authenticity, elegance and the unique charm of Montalcino.
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Montalcino: Brunello Wine Tasting & Vineyard Tour
40 minutes
Free Cancellation
5.0
(1)
from
US$54
For true wine-lovers, there’s no greater thrill than seeing where Tuscany’s specialty red is made. During this in-depth tour of an organic, family-run winery, you’ll learn the ins and outs of Chianti Classico. Tour the scenic vineyard and sample four different red wine varieties inside the atmospheric on-site cellar. Pair your tasting with fresh cheeses and salami, all made from fresh regional products.
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Greve in Chianti Wine Tasting and Winery Tour
1 hour 30 minutes
Free Cancellation
4.7
(122)
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US$60
If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine of the Chianti lands, immersed in the green countryside, this is the tour for you. The small group size of no more than 6 pax will make you appreciate the tranquility and peace of Chianti
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Open Top Van!! Half Day in Chianti with Wine Tasting
4 to 5 hours
Free Cancellation
5.0
(9)
from
US$179
Price varies by group size
Enjoy an unforgettable day: let yourself be guided through the rolling hills and vineyards while admiring the beautiful Tuscan landscapes! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking. Thanks to this tour you will be able to appreciate wines and food and to learn more about our history and traditions: in two words, our Tuscan life style!
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Gourmet Wine Tour
5 hours
5.0
(1)
from
US$333
Price varies by group size
A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and immerse yourself in Val d’Orcia! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking. Thanks to this tour you will be able to appreciate wines and food and learn more about our history and traditions: in two words, our Tuscan life style! 10.00am Departure from Montalcino – Via Circonvallazione, 3 10.10am Arrive at MARTOCCIA . 11.45am Will reach PIOMBAIA – Biodynamic estate 1.00pm lunch in the historical villa, (4 coursed menù) After lunch, guided visit of the cellar 3.45pm We'll reach SAN CARLO estate. 3.15pm We move towards the historical cellar of CONTI COSTANTI, one of the oldest of Montalcino’s area. 7.00pm We’ll return to Montalcino – via Circonvallazione, 3
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Montalcino wine tour
9 hours
4.2
(6)
from
US$440
Price varies by group size
Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative. Tasport From Montalcino
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From Montalcino Brunello di Montalcino Wine Tour with Lunch
2 hours 30 minutes
Free Cancellation
5.0
(9
Operators
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from
US$142
WHAT TO EXPECT Picnic basket with typical products Inside, in fact, you will find not only a comfortable blanket and compostable and recyclable tableware, but also a selection of typical Tuscan products such as bruschetta and a selection of 0 kilometer cured meats and cheeses. Experience in contact with nature After walking through the vineyards and breathing in the scent of the vines, you can choose the place that best belongs to you, where you can enjoy your bottle of wine and your picnic comfortably sitting on your blanket. Bottle of wine of your choice When booking this fabulous picnic, you can choose between a bottle of Rosso di Montalcino or a bottle of Brunello di Montalcino. This choice is fundamental: it will in fact be what will accompany lunch in front of the wonderful spectacle that nature gives you. Both wines are produced by the farm you are on. In fact, you can taste your wine while sitting among the vines that yield the fruits for divine nectar.
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Montalcino: exclusive picnic in the vineyard with wine basket
2 hours
Free Cancellation
4.0
(3)
from
US$36
What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the peaceful atmosphere and timeless beauty of the Montalcino countryside. As the sun sets over the rolling hills, guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the passion and traditions behind Brunello di Montalcino. The evening continues with a curated tasting of exceptional Tuscan wines paired with traditional cuisine, creating a journey where every glass and every dish reflects the soul of Tuscany. From Brunello Riserva selections to handmade pasta and authentic Tuscan flavours, the experience combines elegance, intimacy and a true sense of place. Far from crowded restaurants and commercial tastings, this is a refined and immersive evening designed for those seeking exceptional wines, authentic food and the unforgettable atmosphere of a dinner in the vineyards under the Tuscan sky.
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Montalcino: Brunello Wine Tasting & Tuscan Dinner
3 hours
Free Cancellation
4.8
(5)
from
US$196
Exclusive Gourmet Experience in Montalcino - Wine Tasting with specially developed created Gourmet Bites! For all those who are in the mood for a culinary delight. During a guided wine tasting, you will get served 6 organic wines in 3 flights. Each wine paired with an individual Gourmet Bite. An exciting way to get to know us and our wines.
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Gourmet Wine & Food Tasting
1 hour 30 minutes
Free Cancellation
4.8
(10)
from
US$83
Discover three of Tuscany’s most beautiful towns as you explore Pienza, Montalcino, and Montepulciano in one day on this walking tour. With a private guide, see the splendid 16th-century Renaissance palaces of Montepulciano and walk through the town of Pienza, built by Pope Pius II. In Montalcino, take a guided tour of a winery and taste the renowned Brunello de Montalcino wine. Note: transportation is not included.
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Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting
8 hours
Free Cancellation
5.0
(1)
from
US$417
Per group
Step into the heart of Tuscan cuisine and enjoy a fun, hands-on cooking experience in Chianti, where food, wine, and good company come together. Led by a professional chef, this interactive class will guide you through the preparation of two of Italy’s most beloved dishes: pizza and tiramisu. This experience is designed to be relaxed, social, and engaging—perfect for travelers of all skill levels. Whether you’re a beginner or a food lover, you’ll enjoy learning in a welcoming atmosphere while sharing laughs and stories with fellow participants. Once the cooking is done, sit down and enjoy the meal you’ve prepared, accompanied by local wine. It’s the perfect moment to relax, connect, and savor the authentic flavors of Tuscany. More than just a cooking class, this is a true Italian experience—where you cook, eat, drink, and create lasting memories.
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Best of Florence: Pizza & Tiramisu Cooking Class with Wine
3 hours
Free Cancellation
5.0
(2)
from
US$137
Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce our high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative.
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Brunello Wine Tasting with typical Tuscan Lunch
2 hours 30 minutes
Free Cancellation
5.0
(2)
from
US$75
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