Top Tuscany Wine Tasting & Winery Tours

Q: Got any more Tuscany trip ideas?

We sure do. Check out our curated lists of hand-picked Tuscany Tours. Top 10 Tuscany 2026 Senior-friendly tours Tuscany The best tours and activities for culture lovers in Tuscany Top Day Trips from Tuscany Things to do in Tuscany this summer View all Tuscany Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Tuscany?

Based on our sales data over the past year, the most popular styles of tours and activities in Tuscany are: Tuscany Cultural & Theme Tours Tuscany Luxury & Special Occasions Tuscany Luxury Tours Tuscany Cultural Tours Tuscany Historical & Heritage Tours View all tour styles in Tuscany →

Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena

Enjiy a full day filled with unforgettable memories and photos of Tuscany's most iconic destinations! Depart from Florence and enjoy a scenic drive to Pisa. …More

Florence, Italy

4.0 (2)

Tuscany Grand Tour from Florence: Pisa,Chianti Wine Tasting,Siena

Enjiy a full day filled with unforgettable memories and photos of Tuscany's most iconic destinations! Depart from Florence and enjoy a scenic drive to Pisa....

10 to 11 hours Free Cancellation

4.0 (2)

from
$191

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and …More

Siena, Italy

5.0 (2)

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and...

5 hours 20 minutes Free Cancellation

5.0 (2)

from
$176

Private Tuscan Pinot Noir Experience: Land of Medici Family

Travel to the heart of Tuscany to discover the hidden Pinot Noir in the Medici land, a hilly area in northern Florence. This area boasts …More

Florence, Italy

5.0 (1)

Private Tuscan Pinot Noir Experience: Land of Medici Family

Travel to the heart of Tuscany to discover the hidden Pinot Noir in the Medici land, a hilly area in northern Florence. This area boasts...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$430

Private Wine Tour Top Wineries, Limousine Service, Florence Tours

This Wine Tour of 9 hours on the beautiful Chianti classico area in Tuscany we will visit top wineries and have lunch, cellar tours, wine …More

Florence, Italy

5.0 (3)

Private Wine Tour Top Wineries, Limousine Service, Florence Tours

This Wine Tour of 9 hours on the beautiful Chianti classico area in Tuscany we will visit top wineries and have lunch, cellar tours, wine...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,056

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 …More

Chianti, Italy

5.0 (4)

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...

1 hour Free Cancellation

5.0 (4)

from
$86

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan …More

Florence, Italy

5.0 (3)

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan...

3 days

5.0 (3)

from
$2,488

Italian Cooking Class in Florence - a market to table tour

Discover the essence of Italy through our "Market to Table" cooking class. Immerse yourself in Florence's vibrant San Lorenzo food market, guided by our expert …More

Florence, Italy

5.0 (2)

Italian Cooking Class in Florence - a market to table tour

Discover the essence of Italy through our "Market to Table" cooking class. Immerse yourself in Florence's vibrant San Lorenzo food market, guided by our expert...

5 hours Free Cancellation

5.0 (2)

from
$283

Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit …More

Arezzo, Italy

5.0 (2)

Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit...

4 to 6 hours Free Cancellation

5.0 (2)

from
$616

Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: …More

Florence, Italy

5.0 (3)

Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer:...

9 hours Hotel pickup offered

5.0 (3)

from
$454

Exclusive Tour from Florence: Siena, Chianti and San Gimignano

This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of …More

Florence, Italy

5.0 (3)

Exclusive Tour from Florence: Siena, Chianti and San Gimignano

This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of...

8 hours Hotel pickup offered

5.0 (3)

from
$879

I've been making cooking class for foreigners coming from all over the word for more than 5 years in Pisa. I find it so exciting …More

Pisa, Italy

5.0 (2)

Pisa Private Cooking Class

I've been making cooking class for foreigners coming from all over the word for more than 5 years in Pisa. I find it so exciting...

1 day 3 hours Free Cancellation

5.0 (2)

from
$102

Wellbeing landscapes: Fonteverde Spa in San Casciano dei Bagni

Landscapes of wellbeing: an exclusive couple experience enjoying the landscapes of wellbeing, the Spa “Fonteverde” and typical products tasting or aperitif. …More

San Casciano dei Bagni, Italy

4.3 (4)

Wellbeing landscapes: Fonteverde Spa in San Casciano dei Bagni

Landscapes of wellbeing: an exclusive couple experience enjoying the landscapes of wellbeing, the Spa “Fonteverde” and typical products tasting or aperitif....

6 hours Free Cancellation

4.3 (4)

from
$101

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 …More

San Gimignano, Italy

5.0 (3)

Truffle Hunting & Truffle Cooking Class

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...

4 hours 30 minutes Free Cancellation

5.0 (3)

from
$350

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint …More

Siena, Italy

5.0 (2)

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint...

9 hours Hotel pickup offered

5.0 (2)

from
$227

Val d Orcia Gourmet Food Tour from Siena

A private tour in a small boutique winery with wine tasting. Gourmet food experience in a local home. Enjoy a taste of several local and …More

Siena, Italy

5.0 (2)

Val d Orcia Gourmet Food Tour from Siena

A private tour in a small boutique winery with wine tasting. Gourmet food experience in a local home. Enjoy a taste of several local and...

7 hours Hotel pickup offered

5.0 (2)

from
$98

Valle del Sole Tasting of 3 wines and EVO oil

A fantastic Wine Tasting on our terrace, where you can see all our vineyards directly, while tasting 3 of our biodynamic wines, a white wine, …More

Lucca, Italy

3.8 (10)

Valle del Sole Tasting of 3 wines and EVO oil

A fantastic Wine Tasting on our terrace, where you can see all our vineyards directly, while tasting 3 of our biodynamic wines, a white wine,...

1 hour Free Cancellation

3.8 (10)

from
$40

The beauty of the landscape all around and the experience of the tipical lunch in a local winery will be unforgettable …More

Florence, Italy

5.0 (3)

San Gimignano and Chianti tour

The beauty of the landscape all around and the experience of the tipical lunch in a local winery will be unforgettable...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$677

Florence and Chianti experience Tour from Lucca Including Wine

Take a day out of your Lucca vacation to visit Florence and the Chianti region, and immerse yourself in Renaissance artwork and renowned wine. You …More

Lucca, Italy

4.3 (3)

Florence and Chianti experience Tour from Lucca Including Wine

Take a day out of your Lucca vacation to visit Florence and the Chianti region, and immerse yourself in Renaissance artwork and renowned wine. You...

9 hours Free Cancellation

4.3 (3)

from
$112

Montalcino: exclusive picnic in the vineyard with wine basket

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 …More

Chianti, Italy

5.0 (1)

Montalcino: exclusive picnic in the vineyard with wine basket

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...

2 hours Free Cancellation

5.0 (1)

from
$35

Full-Day Car Tour Siena San Gimignano and Chianti from Florence

A full-day tour to Siena and to San Gimignano, the medieval town considered a Unesco World Heritage Site. Lunch will be held at the Castle …More

Florence, Italy

5.0 (2)

Full-Day Car Tour Siena San Gimignano and Chianti from Florence

A full-day tour to Siena and to San Gimignano, the medieval town considered a Unesco World Heritage Site. Lunch will be held at the Castle...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$911

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Tuscany Wine Tasting & Winery Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Tuscany Wine Tasting & Winery Tours are:

What are the best kid-friendly options for Tuscany Wine Tasting & Winery Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Tuscany Wine Tasting & Winery Tours are:

View all kid-friendly Tours →

Which Tuscany Wine Tasting & Winery Tours have Instant Confirmation?

Tuscany Wine Tasting & Winery Tours with Instant Confirmation include:

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Which Tuscany Wine Tasting & Winery Tours have Free Cancellation?

Tuscany Wine Tasting & Winery Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Tuscany Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Tuscany Wine Tasting & Winery Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Tuscany trip ideas?

What are the most popular styles of Tours and Activities in Tuscany?