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 →

Private Tasting of Organic Wines in the Cellar in Mugliano

In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different …More

Arezzo, Italy

5.0 (5)

Private Tasting of Organic Wines in the Cellar in Mugliano

In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different...

2 hours Free Cancellation

5.0 (5)

from
$34

Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal

1) A Unique Perspective on Wine – Beyond just tasting, you'll explore wine’s lesser-known by-product: balsamic vinegar, crafted from grape must. 2) An Exclusive and …More

San Gimignano, Italy

4.7 (12)

Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal

1) A Unique Perspective on Wine – Beyond just tasting, you'll explore wine’s lesser-known by-product: balsamic vinegar, crafted from grape must. 2) An Exclusive and...

1 hour 30 minutes Free Cancellation

4.7 (12)

from
$86

Private Chianti CastleWineries Experience from Florence

Imagine sipping world-renowned Chianti wines in an enchanting medieval castle, surrounded by the picturesque hills of Tuscany. This dream can become a reality with a …More

Florence, Italy

5.0 (5)

Private Chianti CastleWineries Experience from Florence

Imagine sipping world-renowned Chianti wines in an enchanting medieval castle, surrounded by the picturesque hills of Tuscany. This dream can become a reality with a...

10 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$623

Villages of Chianti with lunch and tasting in Open Top Van

A fantastic private tour, to discover the medieval villages of Chianti. Thanks to our unique minivan specially modified to fully appreciate the landscape. Enjoy the …More

Florence, Italy

5.0 (6)

Villages of Chianti with lunch and tasting in Open Top Van

A fantastic private tour, to discover the medieval villages of Chianti. Thanks to our unique minivan specially modified to fully appreciate the landscape. Enjoy the...

7 to 8 hours Free Cancellation

5.0 (6)

from
$247

Embark on an unforgettable journey into the culinary traditions and world-renowned wines of Tuscany. The Chianti region is celebrated across the globe for its exceptional …More

Florence, Italy

5.0 (5)

Private Tuscan Dinner from Florence

Embark on an unforgettable journey into the culinary traditions and world-renowned wines of Tuscany. The Chianti region is celebrated across the globe for its exceptional...

7 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$430

Tuscany Tour Siena - San Gimignano - Winery

Our exclusive food and wine tour begins in Siena, one of the most fascinating cities in Tuscany. The day begins with a visit to the …More

Florence, Italy

5.0 (6)

Tuscany Tour Siena - San Gimignano - Winery

Our exclusive food and wine tour begins in Siena, one of the most fascinating cities in Tuscany. The day begins with a visit to the...

8 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$902

Private Tour to Siena and Montalcino from Florence

• Experience for your private group. If you are looking for beautiful sceneries, medieval city and excellent wines, this tour is for you. Explore the …More

Florence, Italy

5.0 (5)

Private Tour to Siena and Montalcino from Florence

• Experience for your private group. If you are looking for beautiful sceneries, medieval city and excellent wines, this tour is for you. Explore the...

9 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$965

Uncork the secrets of traditional Tuscan wine in this hands-on class led by an expert sommelier. Learn the history of Tuscany's wine region, gain insight …More

Florence, Italy

5.0 (5)

Journey through Italian Cheese

Uncork the secrets of traditional Tuscan wine in this hands-on class led by an expert sommelier. Learn the history of Tuscany's wine region, gain insight...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$44

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

Siena, Italy

5.0 (1)

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$320

Discover Organic and Biodynamic Chianti Small Wineries

A deep immersion in the world of Chianti, but with particular attention to the sustainability of wines. The winemakers we have selected are all organic …More

Florence, Italy

5.0 (6)

Discover Organic and Biodynamic Chianti Small Wineries

A deep immersion in the world of Chianti, but with particular attention to the sustainability of wines. The winemakers we have selected are all organic...

8 hours Free Cancellation

5.0 (6)

from
$216

Half day e-bike tour in the land of Brunello starting from the medieval town of Montalcino. The e-bike tour is set on the southern part …More

Chianti, Italy

5.0 (8)

Brunello E-Bike Tour

Half day e-bike tour in the land of Brunello starting from the medieval town of Montalcino. The e-bike tour is set on the southern part...

5 to 6 hours Free Cancellation

5.0 (8)

from
$217

Private Tuscany Excursion. Florence American Cemetery, Greve in Chianti, Winery

An enjoyng driving tour from Florence through the Tuscan countryside with a fluent english speaking driver who will drive you to visit some attractions of …More

Florence, Italy

5.0 (3)

Private Tuscany Excursion. Florence American Cemetery, Greve in Chianti, Winery

An enjoyng driving tour from Florence through the Tuscan countryside with a fluent english speaking driver who will drive you to visit some attractions of...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$114

Private Tuscany Tour from Florence Including the Leaning Tower of Pisa and Sangimignano

Take a private amazing day trip through the hills of the Tuscan countryside. Stop to visit the Leaning Tower of Pisa and Sangimignano, the most …More

Florence, Italy

5.0 (2)

Private Tuscany Tour from Florence Including the Leaning Tower of Pisa and Sangimignano

Take a private amazing day trip through the hills of the Tuscan countryside. Stop to visit the Leaning Tower of Pisa and Sangimignano, the most...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,109

Cooking Class of Local Food in a Tuscan Farm

Discover the secrets of Tuscan cuisine in Vinci, in our historic "Podere" between history and breathtaking landscapes. Enjoy local flavors from our gardens while sipping …More

5.0 (2)

Cooking Class of Local Food in a Tuscan Farm

Discover the secrets of Tuscan cuisine in Vinci, in our historic "Podere" between history and breathtaking landscapes. Enjoy local flavors from our gardens while sipping...

2 hours 30 minutes Free Cancellation

5.0 (2)

from
$114

Private Vespa Tour in Chianti from Florence

The Vespa Experience offers a unique and stylish way to explore Tuscany. Forget the chaos of daily life and enjoy the region’s stunning landscapes from …More

Florence, Italy

5.0 (9)

Private Vespa Tour in Chianti from Florence

The Vespa Experience offers a unique and stylish way to explore Tuscany. Forget the chaos of daily life and enjoy the region’s stunning landscapes from...

6 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$280

The Grand Wine Tour – 2 wineries with Chianti & SuperTuscan

You will discover Tuscany with its nuances, walking through the wines with our Sommelier, happy to introducing you the reality of the wine that distinguishes …More

Lucca, Italy

5.0 (9)

The Grand Wine Tour – 2 wineries with Chianti & SuperTuscan

You will discover Tuscany with its nuances, walking through the wines with our Sommelier, happy to introducing you the reality of the wine that distinguishes...

7 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$170

The classics - Guided tour with DOC Bolgheri tasting

We offer a unique experience in the heart of the Bolgheri DOC where you will discover the company philosophy through the tasting of our wines. …More

Livorno, Italy

5.0 (6)

The classics - Guided tour with DOC Bolgheri tasting

We offer a unique experience in the heart of the Bolgheri DOC where you will discover the company philosophy through the tasting of our wines....

2 hours Free Cancellation

5.0 (6)

from
$46

Think of a romantic meal in the Olive Trees shade, accompanied by Tuscan wines!

Our Farmhouse lies on a fascinating position on the Tuscan hills. It is surrounded by a vast stretch of olive groves and vineyards of our …More

Montepulciano, Italy

4.4 (14)

Think of a romantic meal in the Olive Trees shade, accompanied by Tuscan wines!

Our Farmhouse lies on a fascinating position on the Tuscan hills. It is surrounded by a vast stretch of olive groves and vineyards of our...

3 hours Free Cancellation

4.4 (14)

from
$109

Gourmet tour in the Montepulciano old town center

Explore Montepulciano like a local on a relaxed food and wine walking tour through the historic center. Enjoy stunning views, medieval streets, and the authentic …More

Montepulciano, Italy

4.1 (10)

Gourmet tour in the Montepulciano old town center

Explore Montepulciano like a local on a relaxed food and wine walking tour through the historic center. Enjoy stunning views, medieval streets, and the authentic...

3 hours Free Cancellation

4.1 (10)

from
$154

Montepulciano Pienza Montalcino Tour from Siena

Today we will drive you to the famous Orcia Valley, one of the most beautiful area in Tuscany. Here we will visit 3 stunning medieval …More

Chianti, Italy

5.0 (5)

Montepulciano Pienza Montalcino Tour from Siena

Today we will drive you to the famous Orcia Valley, one of the most beautiful area in Tuscany. Here we will visit 3 stunning medieval...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$1,128

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?

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:

View all Tours with Instant Confirmation →

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?