The Chianti region offers excellent wine tours for travelers seeking to experience Tuscany’s famous vineyards.
These tours typically include visits to family-run wineries, tastings of Chianti Classico and Brunello wines, and opportunities to explore charming hilltop villages.
We love the tours that combine wine tasting with local food, as they provide a well-rounded Tuscan experience.
Tours focusing on organic and sustainable winemaking practices are particularly interesting and educational.
For those wanting a more exclusive experience, private tours with gourmet meals are available.
Check out our list of top Chianti wine tours below.
Good To Know
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The Fattoria di Montemaggio Tour offers a 1.5-hour vineyard visit, wine education session, and sampling of 3-6 wines paired with local bread and olive oil.
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The Corte Pavone Gourmet Tasting is a 3-hour experience featuring 6 different Brunelli or Montalcino wines paired with 6 homemade gourmet appetizers.
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The Private Cooking Class and Wine Tasting in Radda in Chianti includes a hands-on workshop on classic Italian dishes and a tasting of wines and olive oil.
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The Gourmet Wine Tour in Chianti is a full-day excursion through the picturesque region, with wine tastings, a delightful lunch, and round-trip transportation.
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The Historic Cellar Tour in Montalcino features two wine tastings and a visit to a historic winery, including a glass of renowned Brunello di Montalcino.
Greve in Chianti Wine Tasting and Winery Tour
After a scenic drive through the rolling hills of Chianti, you’ll arrive at the Azienda Agricola Mauricio Brogioni Winery in Greve in Chianti.
This family-run, organic winery offers a 110-review, 90% traveler-recommended tour. You’ll learn about the renowned Chianti Classico made from Sangiovese grapes and sample four red wine varieties paired with fresh cheeses and salami.
The scenic vineyard tour and access to the on-site cellar enhance the experience. While most guests rave about the knowledgeable hosts and enjoyable tastings, some report issues with booking clarity, tour duration, and value.
Regardless, this intimate winery visit promises to immerse you in the heart of Chianti’s winemaking tradition.
Read our full review: Greve in Chianti Wine Tasting and Winery Tour Review
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Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
Explore the heart of Chianti Classico at the Fattoria di Montemaggio, an organic winery nestled in the rolling hills.
This 1.5-hour tour and tasting offers an immersive experience, with a vineyard visit, wine education, and sampling of 3-6 wines paired with local bread and olive oil.
Led by the knowledgeable Francesco, you’ll learn about the winery’s sustainable practices and Chianti’s rich winemaking heritage.
While the winery’s remote location may require extra travel time, the picturesque setting and informative tour make it well worth the effort.
With a 98% traveler recommendation and a lowest price guarantee, this is a must-do for anyone visiting the Chianti region.
Read our full review: Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area Review
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Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
If you’re looking to discover the stunning Chianti wine region and the picturesque Tuscan countryside during your cruise stop in Livorno, the Chianti and Tuscany Countryside Private Wine Tour is an excellent choice.
This 9-hour private tour offers a scenic drive with stops at Greve-in-Chianti and local wineries, where you’ll learn about the winemaking process and sample local wines and olive oils.
With a 98% traveler recommendation rate, this tour promises a worry-free shore excursion, including pickup at the cruise port and transport in an air-conditioned vehicle.
While the tour doesn’t include meals, it offers a relaxing and informative experience exploring the heart of Tuscany’s wine country.
Read our full review: Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour Review
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Winery Tour & Wine Tasting in Montalcino
Discover the renowned Montalcino wine region with a winery tour and tasting at Corte Pavone. This highly-rated experience offers 6 different wines from Montalcino and/or Maremma, along with a tour of the vineyard and winemaking process.
Explore the beautiful location, learn about grape varieties and wine differences, and enjoy an in-depth, small-group experience. With a 90% recommendation rate and a Badge of Excellence, this tour provides an educational and enjoyable tasting opportunity.
However, some past visitors noted higher prices and less detailed explanations compared to other wineries. This is a unique chance to learn about the renowned Montalcino wine culture.
Read our full review: Winery Tour & Wine Tasting in Montalcino Review
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Private Tuscan Cooking Class and Wine Tasting in Radda in Chianti With Giorgia
Set out on a captivating private Tuscan cooking class and wine tasting experience in the picturesque town of Radda in Chianti with the guidance of Giorgia.
In this 5.0-rated workshop, you’ll learn to create three classic Italian dishes, including homemade pasta. Savor a starter of Panzanella, followed by a main of homemade pasta with ragu. Complement your meal with roasted seasonal vegetables and finish with a delightful Tiramisu.
Between cooking, indulge in a wine and olive oil tasting, with vegetarian and vegan options available. This scenic countryside experience is highly praised for its educational and enjoyable nature, making it a must-do activity in the Chianti region.
Read our full review: Private Tuscan Cooking Class and Wine Tasting in Radda in Chianti With Giorgia Review
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Radda in Chianti: Wine Tasting Tour With Lunch at the Castle
Spend an afternoon exploring the historic Monterinaldi Castle in Radda in Chianti, where you’ll indulge in a guided wine tasting tour and savor a traditional Tuscan lunch.
Led by a knowledgeable sommelier, you’ll discover the castle’s cellars and sample three distinct wines and a dessert vinsanto.
Afterward, you’ll enjoy a 3-course meal with wine pairings in an 18th-century villa.
With a rating of 4.5 from 8 reviews, this experience offers a chance to learn about Chianti’s winemaking heritage.
While some guests noted pacing issues and wine quality concerns, the majority praised the tranquil setting, informative tours, and delectable cuisine.
At $93.37 with a lowest price guarantee, this tour provides excellent value.
Read our full review: Radda in Chianti: Wine Tasting Tour With Lunch at the Castle Review
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Winery Tour & Gourmet Tasting in Montalcino
Venture to the renowned Corte Pavone Winery in Montalcino, where you’ll indulge in a delightful winery tour and gourmet tasting experience.
With 100% traveler recommendation and rave reviews, this 3-hour tour offers an exceptional value at just $87.87 per person.
Savor 6 different Brunelli or wines from Montalcino, each expertly paired with 6 homemade gourmet appetizers sourced from organic-biodynamic agriculture.
The tour is capped at 25 travelers, ensuring an intimate setting.
Easily access the winery by driving from Montalcino towards Grosseto, turning right after 1 km, and following the avenue of cypress trees.
Don’t miss this chance to learn about the flavors of Tuscany.
Read our full review: Winery Tour & Gourmet Tasting in Montalcino Review
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Classic Wine Tasting in Montalcino
Savor a classic wine tasting experience at the renowned Corte Pavone Winery in Montalcino.
Sample 6 different wines from the Montalcino and Maremma regions, choosing from 4 options. At just $32.95, this tour offers exceptional value with a lowest price guarantee.
The winery is easily accessible, with clear directions from Montalcino towards Grosseto. Enjoy the included alcoholic beverages and bottled water, as well as all fees and taxes.
While the experience isn’t wheelchair accessible, it’s stroller-friendly, and service animals are welcome.
With a maximum of 20 travelers, you’ll savor an intimate tasting. Free cancellation is available up to 24 hours in advance, providing flexibility.
Read our full review: Classic Wine Tasting in Montalcino Review
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Montalcino Wine Tour
A Montalcino wine tour is the perfect way to explore the region’s renowned Brunello di Montalcino. This full-day tour takes you to four different cellars, where you’ll enjoy a guided visit and tutored tasting.
Savor a light lunch paired with Rosso and Brunello di Montalcino, accompanied by snacks and alcoholic beverages. The air-conditioned vehicle ensures a comfortable journey, and the knowledgeable tour guide provides insights into the winemaking process.
With a maximum of 8 travelers, you’ll have an intimate and personalized experience. At $384.45 per person, this tour offers excellent value for Brunello lovers, as highlighted by the positive reviews.
Just note that it’s not wheelchair accessible, but strollers are allowed.
Read our full review: Montalcino Wine Tour Review
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Two Wine Tastings and Visit to a Historic Cellar Inside Old Walls of Montalcino
Enjoy the rich winemaking heritage of Montalcino during this captivating tour.
You’ll enjoy two wine tastings and visit a historic cellar within the ancient walls of this charming town. Start with a guided tasting of 3 wines at a historic winery, then savor a glass of renowned Brunello di Montalcino in a city center wine shop.
You’ll also receive a detailed digital itinerary to explore the area at your own pace. With a maximum group size and private tour, you’ll enjoy a personalized experience.
While not suitable for those with mobility issues, most travelers can participate in this highly recommended tour.
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Wine Tasting, Dinner and Cooking Class Under the Sunset
After exploring the historic winemaking traditions of Montalcino, you’ll now have the chance to learn about the local culinary culture through a hands-on cooking class, wine tasting, and delectable dinner.
You’ll learn to make traditional ‘pinci’ pasta using local flour, then savor your homemade creation with a Tuscan sauce and typical cakes, accompanied by five tastings of the renowned Brunello di Montalcino wines.
This small-group experience, limited to 8 participants, includes round-trip hotel transfers and transport by air-conditioned minivan.
Whether you’re a food and wine aficionado or simply looking to discover the flavors of Tuscany, this half-day culinary adventure is sure to delight.
Read our full review: Wine Tasting, Dinner and Cooking Class Under the Sunset Review
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3-Hour Private Food and Wine Experience in Montalcino
Get ready to indulge in a private culinary journey through the heart of Montalcino, where you’ll savor the flavors of Tuscany.
This 3-hour experience immerses you in the region’s food and wine traditions. Delight in an appetizer from the renowned Molino di Sant’Antimo, followed by seasonal recipes from the Vittori family.
Finish with their signature desserts paired with a wine tasting. With a 5-star rating and private tour for your group, you’ll enjoy a personalized experience in a wheelchair and stroller accessible setting.
Priced at $131.81, this is a must for any Chianti enthusiast seeking an authentic taste of the region.
Read our full review: 3-Hour Private Food and Wine Experience in Montalcino Review
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Gourmet Wine Tour
Embark on an unforgettable gourmet wine tour through the picturesque Chianti region.
This 5-star rated experience includes a full-day excursion with wine tastings, a delightful lunch, and round-trip transportation by air-conditioned minivan.
You’ll be picked up from your selected hotel and taken to the charming town of Montalcino, where you’ll visit a local winery and savor the region’s renowned Tuscan wines.
The tour also provides a vegetarian option, ensuring everyone can indulge in the gourmet delights.
With a maximum of 8 travelers, you’ll enjoy a personalized and intimate exploration of Chianti’s winemaking heritage.
Don’t miss this opportunity to learn about the flavors of this iconic Italian destination.
Read our full review: Gourmet Wine Tour Review
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Private Hike and Wine Experiences in Chianti
For a truly immersive exploration of Chianti’s natural wonders and world-renowned wines, consider booking a Private Hike and Wine Experiences in Chianti.
This private tour offers a chance to hike through the picturesque Chianti region and enjoy wine tastings at local wineries. The tour starts in Greve in Chianti, with a meeting point at the Piazza Matteotti.
The hike is moderate, and the tour includes a lunch featuring Tuscan specialties like bruschetta, cheese, and prosciutto, as well as a pasta dish.
Private transportation, knowledgeable guides, and free cancellation up to 24 hours before the experience make this tour a convenient and enjoyable way to discover the beauty and flavors of Chianti.
Read our full review: Private Hike and Wine Experiences in Chianti Review
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Grand Tour of Pienza, Montalcino, Montepulciano Wine and Cheese Tasting
Exploring the charming Tuscan towns of Pienza, Montalcino, and Montepulciano in a single day, this Grand Tour offers a comprehensive immersion into the region’s renowned wine and cheese heritage.
You’ll visit the UNESCO-listed Pienza, discover Renaissance palaces in Montepulciano, and enjoy a guided winery tour and tasting in Montalcino.
Savor local pecorino cheese and Tuscan wines, while your private guide shares the history of each destination.
With private transportation and a small cheese tasting included, this tour provides a seamless and intimate experience.
Priced at $384.45 per group, it’s a Lowest Price Guarantee, with free cancellation up to 24 hours in advance.
Read our full review: Grand Tour of Pienza, Montalcino, Montepulciano Wine and Cheese Tasting Review
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Frequently Asked Questions
What Is the Best Time of Year to Visit Chianti for Wine Tours?
The best time to visit Chianti for wine tours is typically spring or fall. You’ll enjoy mild weather, fewer crowds, and the opportunity to see the vineyards in their most vibrant seasons.
Can I Bring My Own Food on a Chianti Wine Tasting Tour?
You can typically bring your own food on a Chianti wine tasting tour, though some tours may provide a light lunch or snacks. It’s always best to check with the tour operator beforehand to understand their policies.
Do I Need to Make Reservations for Chianti Winery Tours in Advance?
Yes, it’s generally recommended to make reservations for Chianti winery tours in advance. This ensures you’ll have a spot on the tour and can avoid disappointment, as many popular wineries book up, especially during peak seasons.
Are There Any Age Restrictions for Chianti Wine Tasting Tours?
Most Chianti wine tasting tours don’t have strict age restrictions, but you’ll need to be at least 18 to participate. Check with the specific wineries beforehand to confirm their policy. Reservations are generally recommended to guarantee your spot.
Can I Customize My Chianti Wine Tour Experience to Suit My Preferences?
Yes, you can often customize your Chianti wine tour experience to suit your preferences. Many tour operators allow you to choose the wineries, activities, and pace that best fit your interests and needs.
The Sum Up
Explore Chianti’s renowned wineries and savor the flavors of Tuscany. From private tours to cooking classes, there’s something for every wine enthusiast. Discover organic vineyards, indulge in Montalcino’s renowned Brunello, and enjoy the breathtaking countryside. Whether you’re a seasoned oenophile or a curious newcomer, these experiences will leave you with unforgettable memories of Chianti’s rich wine culture.