Top Tuscany Wine Tasting & Winery Tours

Q: Got any more Tuscany trip ideas?

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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 Chianti Classico wine tour - 2 wineries + lunch

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

Lucca, Italy

5.0 (2)

Private Chianti Classico wine tour - 2 wineries + lunch

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...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$307

Essence of Tuscany - Private Wine & Evo oil Tasting

✅ Exclusive Wine, Olive Oil Tasting & Balsamic Vinegar tasting – Savor a selection of our organic wines and extra virgin olive oils, straight from …More

San Gimignano, Italy

4.7 (26)

Essence of Tuscany - Private Wine & Evo oil Tasting

✅ Exclusive Wine, Olive Oil Tasting & Balsamic Vinegar tasting – Savor a selection of our organic wines and extra virgin olive oils, straight from...

1 hour Free Cancellation

4.7 (26)

from
$57

Private Wine & Evo Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

San Gimignano, Italy

4.9 (18)

Private Wine & Evo Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes Free Cancellation

4.9 (18)

from
$78

Experience the unique history of the Marquis Gondi and the Bossi Estate: where one of the most ancient Florentine families continue to produce wine for …More

Florence, Italy

5.0 (2)

Wine Tasting Activity at Chianti Rufina

Experience the unique history of the Marquis Gondi and the Bossi Estate: where one of the most ancient Florentine families continue to produce wine for...

1 hour Free Cancellation

5.0 (2)

from
$24

Private Grape stomping in Chianti from Florence

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

Florence, Italy

5.0 (12)

Private Grape stomping in Chianti from Florence

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 to 6 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$280

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
$482

Excellent Wine experience in English, Español, Purtuguês

On this tour we will visit two of the most beautiful cities in Tuscany, important both for art and culture and of considerable historical importance. …More

Florence, Italy

5.0 (12)

Excellent Wine experience in English, Español, Purtuguês

On this tour we will visit two of the most beautiful cities in Tuscany, important both for art and culture and of considerable historical importance....

8 hours Hotel pickup offered

5.0 (12)

from
$861

An approach to tasting our wines with a focus on food-wine pairing. Suggestions and experiences in a glass, to become a real taster. …More

San Gimignano, Italy

5.0 (4)

"Gourmet" Wine Tasting at Cesani's

An approach to tasting our wines with a focus on food-wine pairing. Suggestions and experiences in a glass, to become a real taster....

1 hour 45 minutes Free Cancellation

5.0 (4)

from
$69

Wine Tasting Experience in Florence city centre

In Florence, a few steps from the Duomo, there is a special experience going on: an exclusive Italian wine tasting experience. Don’t miss this chance …More

Florence, Italy

4.3 (7)

Wine Tasting Experience in Florence city centre

In Florence, a few steps from the Duomo, there is a special experience going on: an exclusive Italian wine tasting experience. Don’t miss this chance...

1 hour Free Cancellation

4.3 (7)

from
$45

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a …More

Siena, Italy

5.0 (11)

Wine Tuk Tour Siena

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a...

3 hours

5.0 (11)

from
$149

San Gimignano: Chianti wine tasting and lunch

A few steps from San Gimignano do not miss a special food and wine experience: a tasting of the best Chianti wines with lunch included …More

San Gimignano, Italy

5.0 (2)

San Gimignano: Chianti wine tasting and lunch

A few steps from San Gimignano do not miss a special food and wine experience: a tasting of the best Chianti wines with lunch included...

2 hours Free Cancellation

5.0 (2)

from
$79

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
$261

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

Siena, Italy

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

Guided tour with wine tasting and local organic products

The guided tour of our winery and facilities is unique for its contents and the architectural richness of our environments, as well as for the …More

Florence, Italy

5.0 (12)

Guided tour with wine tasting and local organic products

The guided tour of our winery and facilities is unique for its contents and the architectural richness of our environments, as well as for the...

2 hours Free Cancellation

5.0 (12)

from
$46

Private Classic Wine Tour in Chianti from Florence

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make …More

Florence, Italy

5.0 (4)

Private Classic Wine Tour in Chianti from Florence

Chianti Classico is more than just wine—it’s a way of life. On this tour, you will discover the passion, history, and unique terroir that make...

7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$300

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic …More

Livorno, Italy

4.9 (10)

Pisa and Florence Private Tour with Wine Tasting

Discover the Essence of Tuscany: Pisa, Florence & Chianti Wine Experience Immerse yourself in the timeless beauty of Pisa and Florence—two of Tuscany’s most iconic...

9 hours

4.9 (10)

from
$1,255

Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

San Gimignano, Italy

4.8 (19)

Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes Free Cancellation

4.8 (19)

from
$78

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different …More

Lucca, Italy

5.0 (11)

Wine Tour in the Countryside of Lucca with Lunch - with Minivan

This tour is including a car at your disposal during the tour, transfer to a beautiful winery in Montecarlo where you can taste 4 different...

5 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$195

Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you …More

San Gimignano, Italy

4.8 (16)

Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you...

1 hour 30 minutes Free Cancellation

4.8 (16)

from
$109

Tour of San Gimignano and Private Wine Experience in Chianti

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in …More

Florence, Italy

5.0 (2)

Tour of San Gimignano and Private Wine Experience in Chianti

Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in...

5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$221

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?