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 Bolgheri Experience: Land of the Super Tuscan

Our exclusive Bolgheri wine tour is a curated experience that allows visitors to explore the renowned wine region of Bolgheri in Tuscany. This tour includes …More

Florence, Italy

5.0 (4)

Private Bolgheri Experience: Land of the Super Tuscan

Our exclusive Bolgheri wine tour is a curated experience that allows visitors to explore the renowned wine region of Bolgheri in Tuscany. This tour includes...

10 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (4)

from
$754

There is nothing as unique and romantic as enjoying the sunset among vineyards and olive groves. Our sunset bike tour is the perfect way to …More

Florence, Italy

5.0 (4)

Private Tuscany Sunset Bike Tour

There is nothing as unique and romantic as enjoying the sunset among vineyards and olive groves. Our sunset bike tour is the perfect way to...

5 hours Free Cancellation

5.0 (4)

from
$203

Private Suvereto Wines Experience: Land of Elisa Bonaparte

Get an introduction into Suvereto’s wine scene! Expand your palate with wines from Southern Tuscany, a region that charms travelers with its medieval architecture and …More

Florence, Italy

5.0 (4)

Private Suvereto Wines Experience: Land of Elisa Bonaparte

Get an introduction into Suvereto’s wine scene! Expand your palate with wines from Southern Tuscany, a region that charms travelers with its medieval architecture and...

12 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$744

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

Quad excursion in the woods with visit to the cellar and tasting

Come and try an authentic Maremma experience! Quad excursions to discover the "Bandite di Scarlino" woods with visit to the cellar and wine tasting. Suggestive …More

4.8 (4)

Quad excursion in the woods with visit to the cellar and tasting

Come and try an authentic Maremma experience! Quad excursions to discover the "Bandite di Scarlino" woods with visit to the cellar and wine tasting. Suggestive...

2 hours 30 minutes Free Cancellation

4.8 (4)

from
$103

Visit Of The Chianti Classico And The Tuscan Countryside

You will have an unique experience with speaking English driver, you will feel the real atmosphere of Tuscany in the beauty of the Nature and …More

Florence, Italy

5.0 (4)

Visit Of The Chianti Classico And The Tuscan Countryside

You will have an unique experience with speaking English driver, you will feel the real atmosphere of Tuscany in the beauty of the Nature and...

8 hours Free Cancellation

5.0 (4)

from
$250

Private Tuscan Cooking Class & Wine Tasting from Florence

Enjoy a private Tuscan cooking class set in a family Tuscan home boutique, overlooking the hills of Tuscany. One of the best ways to embrace …More

Florence, Italy

5.0 (3)

Private Tuscan Cooking Class & Wine Tasting from Florence

Enjoy a private Tuscan cooking class set in a family Tuscan home boutique, overlooking the hills of Tuscany. One of the best ways to embrace...

7 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$566

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 …More

Chianti, Italy

5.0 (3)

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...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$67

A Classic Tuscan Winery with Lunch in Montepulciano

Stop and savor Tuscany, tasting our wines, enjoying a light lunch and the typical flavors of this region. You will visit a hundred-year old wine …More

Montepulciano, Italy

5.0 (3)

A Classic Tuscan Winery with Lunch in Montepulciano

Stop and savor Tuscany, tasting our wines, enjoying a light lunch and the typical flavors of this region. You will visit a hundred-year old wine...

1 hour 45 minutes Free Cancellation

5.0 (3)

from
$102

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti. …More

Siena, Italy

5.0 (3)

Wine & Cheese Experience

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti....

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$68

Winery Tour & Tasting in Pisa Countryside

There's no better way to discover Italy's culture from the inside. Our national network of expert Italian home cooks offers the finest Italian food experiences. …More

Livorno, Italy

5.0 (3)

Winery Tour & Tasting in Pisa Countryside

There's no better way to discover Italy's culture from the inside. Our national network of expert Italian home cooks offers the finest Italian food experiences....

2 hours Free Cancellation

5.0 (3)

from
$40

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello …More

Siena, Italy

5.0 (3)

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$262

Private Chianti with Lunch Half Day Experience from Florence

Discover the symbiosis between wine and food! In Italy, pairing food with wine is sacred, as it amplifies the flavors and creates a perfect balance. …More

Florence, Italy

5.0 (3)

Private Chianti with Lunch Half Day Experience from Florence

Discover the symbiosis between wine and food! In Italy, pairing food with wine is sacred, as it amplifies the flavors and creates a perfect balance....

7 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$431

Wine tasting of the great wines of Tuscany with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023, 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022. We can organize the …More

Lucca, Italy

5.0 (3)

Wine tasting of the great wines of Tuscany with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023, 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022. We can organize the...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$104

Discover Montalcino through its best productions: Brunello & Saffron!!

Enjoy an unforgettable day: let us guide you through the rolling hills and vineyards to discover the local flavors and scents Montalcino is a land …More

Chianti, Italy

5.0 (3)

Discover Montalcino through its best productions: Brunello & Saffron!!

Enjoy an unforgettable day: let us guide you through the rolling hills and vineyards to discover the local flavors and scents Montalcino is a land...

3 hours 30 minutes

5.0 (3)

from
$240

Garden Tour and Authentic Italian Pasta Making Class in Tuscany

This Tuscany cooking class is ideal for anyone looking to dive into Italian culture, learn new cooking skills, and spend time with welcoming locals in …More

5.0 (3)

Garden Tour and Authentic Italian Pasta Making Class in Tuscany

This Tuscany cooking class is ideal for anyone looking to dive into Italian culture, learn new cooking skills, and spend time with welcoming locals in...

3 hours Free Cancellation

5.0 (3)

from
$135

Private Val d'Orcia Experience - A cinematic universe

Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting Val d’Orcia, a Unesco World Heritage Site. The …More

Florence, Italy

5.0 (3)

Private Val d'Orcia Experience - A cinematic universe

Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting Val d’Orcia, a Unesco World Heritage Site. The...

12 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$658

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes …More

Florence, Italy

5.0 (3)

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes...

10 hours Hotel pickup offered

5.0 (3)

from
$276

Make your bland bottle and cork Your wine in center of Florence

This is the only wine workshop in Florence where you can create your personal blend. A small group that allows you to be pampered with …More

Florence, Italy

5.0 (3)

Make your bland bottle and cork Your wine in center of Florence

This is the only wine workshop in Florence where you can create your personal blend. A small group that allows you to be pampered with...

1 hour 45 minutes

5.0 (3)

from
$148

3-Hour Private Food and Wine Experience in Montalcino

Guests will be immersed in the countryside of the southern area of Montalcino and will enter the atmosphere of Molino di Sant'Antimo and the tradition …More

Chianti, Italy

5.0 (3)

3-Hour Private Food and Wine Experience in Montalcino

Guests will be immersed in the countryside of the southern area of Montalcino and will enter the atmosphere of Molino di Sant'Antimo and the tradition...

3 hours

5.0 (3)

from
$138

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:

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?