Top Chianti Wine Tasting Tours

Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

2 hoursFree Cancellation

4.9

(134)

from $47

Greve in Chianti Wine Tasting and Winery Tour

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.

Greve in Chianti Wine Tasting and Winery Tour

Winery Tour & picnic in the vineyard with a bottle of wine

4.7

(121)

from $58

2 hours 30 minutesFree Cancellation

4.7

(7)

from $47

Experience the authentic side of Tuscan cuisine with this exclusive farmhouse cooking class. Meet your local host at their farm in the Chianti hills and enjoy a hands-on lesson to learn how to turn out fresh ravioli or “pici” pasta, beef ragu or other sauces, pizza dough, and chocolate “salami”. Relax over a homecooked meal after your lesson to enjoy the dishes you've prepared paired with local wine.

Cooking Class on a Family Farm in Chianti with Lunch

4 hoursFree Cancellation

(177)

from $169

Winery tour & wine tasting in Montalcino

1 hour 45 minutesFree Cancellation

4.4

(42)

from $47

Brunello Wine Tasting with typical Tuscan Lunch

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.

Brunello Wine Tasting with typical Tuscan Lunch

2 hours 30 minutesFree Cancellation

Classic Wine Tasting in Montalcino

(2)

from $73

45 minutesFree Cancellation

4.8

(8)

from $35

In the Heart of Chianti Classico : Wine, Winery and Tradition

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.

In the Heart of Chianti Classico : Wine, Winery and Tradition

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.

(3)

from $40

Montalcino: Brunello Wine Tasting & Tuscan Lunch

Montalcino: Brunello Wine Tasting & Tuscan Lunch

Private Tuscan Cooking Class And Wine Tasting in Radda in Chianti

(9)

from $114

3 hoursFree Cancellation

Live an authentic experience in the heart of Chianti, on the family farm in Montefioralle. We will welcome you in a warm and traditional environment to let you discover the wines, oil and Tuscan cuisine. During the experience you will taste rich traditional chopping boards made with locally sourced and strictly homemade (non-industrial) products, special wines, personally produced olive oil and final dessert. After the tasting, for those who wish, it will be possible to take a short walk through the vineyards to discover how the wine is born. We believe in a simple, authentic and genuine welcome. Here you will not find an experience built for tourists, but a real moment of Tuscan life, made of wine, food and conviviality.

(12)

from $166

Tasting in the Farm of Wines Oil and Local Products

Tasting in the Farm of Wines Oil and Local Products

1 to 2 hoursFree Cancellation

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!

(2)

from $47

Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

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.

(6)

from $45

Wine Tasting in an Authentic Tuscan Cellar in Radda in Chianti

Wine Tasting in an Authentic Tuscan Cellar in Radda in Chianti

1 hourFree Cancellation

4.5

from $37

Montalcino: Brunello Wine Tasting with Tuscan Specialities

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.

Montalcino: Brunello Wine Tasting with Tuscan Specialities

1 hourFree Cancellation

4.7

(7)

from $87

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

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.

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

8 hoursFree Cancellation

(1)

from $408

Per group

Winery Tour & Gourmet Tasting in Montalcino

2 hours 30 minutesFree Cancellation

We are Federico, Raimondo, and Riccardo, and we’re excited to welcome you on this unforgettable tour! Discover the beauty of our land through its flavors—taste our organic wines, including red Chianti Classico Mariagioconda, rosé Lo Stinto, white Il Pinone, and orange Il Matan, along with our finest extra virgin olive oil and the seasonal vegetable garden we grow. As we explore the breathtaking Chianti landscape, you’ll visit our vineyards and cellar, where we’ll share the secrets of aging and caring for our wines, nurturing both the bottles and the fields. Together, we’ll taste four organic wines and our exceptional olive oil, paired with delicious local cheeses and cold cuts. The tasting will take you on a journey from crisp white native wines to the deep flavors of Sangiovese red. Get ready to immerse yourself in nature and experience its most precious gifts firsthand!

(16)

from $93

Chianti family owned organic wine tasting

Chianti family owned organic wine tasting

1 to 3 hoursFree Cancellation

Cooking Class in a Real Tuscan Farmhouse

from $72

3 hoursFree Cancellation

(16)

from $128

Your experience will start directly at your hotel, where you will climb aboard an air-conditioned vehicle with a professional driver. You will visit a historic wine cellar to discover the aromas of the barrel room and the quiet of the cellars. Enjoy different vintages of local Chianti Classico wines. After, you will be welcomed to a family-run winery to visit the cellar, have a wine tasting, and enjoy a full lunch accompanied by locally produced wines for those who wish to discover the pleasure of local cuisine. In the end of the tour, you will visit a third winery, a biological one. You will visit the cellars and enjoy a guided tasting of three local wines with tastings of olive oil with bread and Cinta Senese Dop cured meats. Please note that the order of visits and the wineries could change due to availability. When select SELF DRIVE OPTION, you have to travel with your OWN car. NO TRANSFER is included. It is NOT possible to take the tour using public transportation.

3 Cellars in Chianti with Visits, Wine Tastings, Lunch&Transfer

3 Cellars in Chianti with Visits, Wine Tastings, Lunch&Transfer

8 hours

Price varies by group size

from $204

Brunello Vineyards Bus Tour

3 hours

Price varies by group size

(11)

from $210

Chianti -Fresh Pasta Making Class and Sauces with Lunch or Dinner

Rather than bringing home souvenirs from your trip to Chianti, this experience allows you to bring home new skills—the knowledge of how to make authentic Italian pasta from scratch. Taking place in a beautiful villa in the Italian countryside, the experience is private, which ensures one-to-one guidance from your instructor. Learn to prepare 2–3 types of fresh pasta with sauces—such as gnocchi, ravioli, and tagliatelle—and then enjoy feasting on them after your lesson.

Chianti -Fresh Pasta Making Class and Sauces with Lunch or Dinner

3 hoursFree Cancellation

Montepulciano Pienza Montalcino Tour from Siena

(23)

from $140

8 to 9 hoursFree Cancellation

(5)

from $1,152

Per group

Much more than a cooking course, it will be a unique experience. Sight, smell, hearing ... in this path the 5 senses will be involved, so as to leave you with an unforgettable memory. This experience comes from a childhood memory, spent outdoors. It has the scent of freshly cut grass, the passion for traditional cuisine and the serenity of an atmosphere that warms up under the notes of the Italian Opera.

Cooking, Dinner & Live Opera in the countryside

Cooking, Dinner & Live Opera in the countryside

3 hours 30 minutesFree Cancellation

4.8

(45)

from $210

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What are people saying about Chianti

Homemade Pasta Class and Lunch in the Heart of Chianti

Megan_S, Jul 2026

The Highlight of Our Honeymoon in Tuscany

If you’re considering this experience, stop thinking and book it. Our pasta-making class with Valentina and Annamaria was one of the absolute highlights of our honeymoon and one of our favorite memories from all of Italy. From the moment we arrived, they welcomed us into their beautiful home like family. Their warmth, kindness, and genuine hospitality made communication effortless. The setting in the Chianti countryside was breathtaking. Learning to make fresh pasta completely by hand was so much fun, and Valentina and Annamaria were incredibly patient, encouraging, and passionate about sharing their family traditions. It never felt like a tourist activity. It felt like being invited into someone’s home to experience authentic Tuscan life. After cooking together, we enjoyed one of the best meals we had during our trip, paired with wonderful local wine and incredible conversation. Every detail was thoughtfully planned, and you could truly feel the love they put into the entire experience. We left not only with new cooking skills, but with memories we’ll treasure for the rest of our lives. Thank you, Valentina and Annamaria, for making us feel like part of your family. We can’t wait to recreate these recipes back home and remember our honeymoon in Tuscany every time we make pasta. Five stars isn’t enough. 🇮🇹❤️🍝

Cooking Class in a Real Tuscan Farmhouse

Joseph_B, Jun 2026

Interesting, delicious and fun.

Great day learning about Tuscan history & cooking in a picturesque location. The team of two ladies were fun, knowledgeable and worked well together to keep things moving at a great pace to complete our preperations and cooked our meal. Couldn't have been better.

Chianti -Fresh Pasta Making Class and Sauces with Lunch or Dinner

Lisa_S, Jun 2026

Tuscany pasta making - great family experience

This was a great way to experience the art of making pasta. The hosts were extremely knowledgeable and passionate. We learned many pasta shapes and ate our creations. The setting was well designed for groups. We relaxed and savored 2 dishes and finished with gelato at lunch.

Cooking Class on a Family Farm in Chianti with Lunch

Jean_S, Apr 2026

Book IT!

Camilla has a beautiful farmhouse that looks over a carpet of Olive trees and grape vines. We made pasta, bread and more! Sat outside and had wine and had more food than you could imagine! There was one other couple so it was a very intimate setting. We loved it! She is a fabulous person. A highlight of our stay! Thanks Camilla!❤️

Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

Ross_P, Aug 2025

Unforgettable Experience and Amazing Wines

It's rare to meet someone as knowledgeable and as passionate for their craft as Francesco is. He provided so much insight and education about the wine making process, and highlighted the importance and uniqueness of the Chianti Region. This was an amazing experience and wonderful wine tasting, and one you should not miss. All of the wines were unique and excellent, and Francesco did a wonderful job of showcasing the subtleties of each wine and style. If you are visiting Tuscany you should visit Fattoria Di Montemaggiore.