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 →

Florence: Chianti Wine Tour & San Gimignano with 2 Wineries

Leave the crowds of Florence behind and discover the beauty of Tuscany on this Chianti morning wine tour. Travel through the iconic Tuscan countryside and …More

Florence, Italy

5.0 (1)

Florence: Chianti Wine Tour & San Gimignano with 2 Wineries

Leave the crowds of Florence behind and discover the beauty of Tuscany on this Chianti morning wine tour. Travel through the iconic Tuscan countryside and...

5 hours 40 minutes Free Cancellation

5.0 (1)

from
$56

Fun wine tasting from our unique selection in the heart of Florence

First of all we are wine lovers and we hope you are too :)) In our cozy tasting room our passion leaded us to find …More

Florence, Italy

5.0 (1)

Fun wine tasting from our unique selection in the heart of Florence

First of all we are wine lovers and we hope you are too :)) In our cozy tasting room our passion leaded us to find...

1 hour Free Cancellation

5.0 (1)

from
$63

Private Montepulciano Wine Experience with Lunch in Local Setting

Immerse yourself in an unforgettable culinary journey through the picturesque hills of Val d'Orcia and Val di Chiana, where the charm of art, history, and …More

Montepulciano, Italy

5.0 (1)

Private Montepulciano Wine Experience with Lunch in Local Setting

Immerse yourself in an unforgettable culinary journey through the picturesque hills of Val d'Orcia and Val di Chiana, where the charm of art, history, and...

4 to 5 hours

5.0 (1)

from
$480

Light lunch and wine tasting in Garfagnana with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022, and it will be …More

5.0 (1)

Light lunch and wine tasting in Garfagnana with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023", 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022, and it will be...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$125

From Florence: Private Cortona & Montepulciano with Wine Lunch

Follow the footsteps of the film "Under the Tuscan Sun" on a private day trip from Florence. Travel through the Tuscan countryside, among vineyards, art …More

Florence, Italy

5.0 (1)

From Florence: Private Cortona & Montepulciano with Wine Lunch

Follow the footsteps of the film "Under the Tuscan Sun" on a private day trip from Florence. Travel through the Tuscan countryside, among vineyards, art...

10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$262

Siena & San Gimignano Private Day Trip with Lunch From Florence

After being picked up from your Florence hotel, the day will start with a trip to Florence's historic rival, Siena! A UNESCO World Heritage site, …More

Florence, Italy

5.0 (1)

Siena & San Gimignano Private Day Trip with Lunch From Florence

After being picked up from your Florence hotel, the day will start with a trip to Florence's historic rival, Siena! A UNESCO World Heritage site,...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$296

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

Guided visit to the winery and ageing cellars followed by a guided tasting of a selection of our best wines and lunch with gastronomic specialities …More

Florence, Italy

5.0 (1)

Lunch with Wine Tasting at the Winery

Guided visit to the winery and ageing cellars followed by a guided tasting of a selection of our best wines and lunch with gastronomic specialities...

2 hours Free Cancellation

5.0 (1)

from
$74

A scenic ride along the Via Francigena to San Gimignano: the home of Vernaccia wine and world-renowned gelato. With our E-bikes you’ll make your way …More

Florence, Italy

5.0 (1)

Chianti to San Gimignano E-bike Tour

A scenic ride along the Via Francigena to San Gimignano: the home of Vernaccia wine and world-renowned gelato. With our E-bikes you’ll make your way...

8 hours Free Cancellation

5.0 (1)

from
$356

Private wine tasting in your Villa in Versilia 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 (1)

Private wine tasting in your Villa in Versilia 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 (1)

from
$64

Private tour of Siena Monteriggioni San Gimignano, Winery, lunch

Our first stop will be in Siena which with its medieval monuments and art treasures is considered a world heritage site by UNESCO. We'll start …More

Florence, Italy

5.0 (1)

Private tour of Siena Monteriggioni San Gimignano, Winery, lunch

Our first stop will be in Siena which with its medieval monuments and art treasures is considered a world heritage site by UNESCO. We'll start...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$238

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
$431

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

Private Photo Shooting on Horseback and at Wine Estate's

A professional photo-shooting on horseback and while tasting the best Chianti wines in a scenic location will give the guests an unbeatable chance to escape …More

Florence, Italy

5.0 (1)

Private Photo Shooting on Horseback and at Wine Estate's

A professional photo-shooting on horseback and while tasting the best Chianti wines in a scenic location will give the guests an unbeatable chance to escape...

6 hours 30 minutes Free Cancellation

5.0 (1)

from
$556

Pasta and Italian Recipes in the Countryside

Cooking Experience & Lunch: Blend Tuscan and Apulian flavors in an historic villa for a unique taste! …More

Chianti, Italy

5.0 (1)

Pasta and Italian Recipes in the Countryside

Cooking Experience & Lunch: Blend Tuscan and Apulian flavors in an historic villa for a unique taste!...

3 hours 30 minutes Free Cancellation

5.0 (1)

from
$160

Wine and Dine in Chianti Classico Exclusive Private Dinner

Step into the warm, intimate setting of the private wine cellar for an unforgettable dining experience. Savor a handcrafted 4-course meal, prepared exclusively for you …More

Florence, Italy

5.0 (1)

Wine and Dine in Chianti Classico Exclusive Private Dinner

Step into the warm, intimate setting of the private wine cellar for an unforgettable dining experience. Savor a handcrafted 4-course meal, prepared exclusively for you...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$284

THE MASTER of Chianti Classico 3 Top Wineries Limousine Service

A wonderful day with many stops for panoramic photos on the beautiful countryside of Chianti classico, the famous countryside of Tuscany, guided from an English …More

Florence, Italy

5.0 (1)

THE MASTER of Chianti Classico 3 Top Wineries Limousine Service

A wonderful day with many stops for panoramic photos on the beautiful countryside of Chianti classico, the famous countryside of Tuscany, guided from an English...

9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,251

Truffle Hunting and Tasting in San Gimignano with a Tuscan Lunch

TOUR HIGHLIGHTS • Join a truffle hunter and his trained dog to go in search of truffles in the wood • Taste eleven local wines, …More

Florence, Italy

5.0 (1)

Truffle Hunting and Tasting in San Gimignano with a Tuscan Lunch

TOUR HIGHLIGHTS • Join a truffle hunter and his trained dog to go in search of truffles in the wood • Taste eleven local wines,...

6 hours Free Cancellation

5.0 (1)

from
$427

Tuscan Food Cooking Class in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Sit down to taste everything you created along with wine tasting from the library vintage reserves • Learn from a passionate local …More

Florence, Italy

5.0 (1)

Tuscan Food Cooking Class in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Sit down to taste everything you created along with wine tasting from the library vintage reserves • Learn from a passionate local...

5 hours Free Cancellation

5.0 (1)

from
$279

Florence Wine Tasting Tour in the City Center! Local Expert!

Discover Florence's rich wine history on this urban wine tour that leads you through the heart of the city. As you stroll through the cities …More

Florence, Italy

5.0 (1)

Florence Wine Tasting Tour in the City Center! Local Expert!

Discover Florence's rich wine history on this urban wine tour that leads you through the heart of the city. As you stroll through the cities...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$97

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?