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 →

San Gimignano & Tuscan Wine Tasting from Florence

Discover the charm of San Gimignano and experience Tuscany's culinary delights on this half-day tour from Florence. Begin your adventure in an air-conditioned van, taking …More

Florence, Italy

5.0 (4)

San Gimignano & Tuscan Wine Tasting from Florence

Discover the charm of San Gimignano and experience Tuscany's culinary delights on this half-day tour from Florence. Begin your adventure in an air-conditioned van, taking...

5 hours Free Cancellation

5.0 (4)

from
$189

Florence Walking Tour Explore Renaissance Gems and Wine Window

Discover the essence of Florence on this intimate walking tour led by a certified local guide. Journey through the historic center, starting in the San …More

Florence, Italy

5.0 (17)

Florence Walking Tour Explore Renaissance Gems and Wine Window

Discover the essence of Florence on this intimate walking tour led by a certified local guide. Journey through the historic center, starting in the San...

2 hours Free Cancellation

5.0 (17)

from
$79

Open Top Van!! Half Day in Chianti with Wine Tasting

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine …More

Chianti, Italy

5.0 (10)

Open Top Van!! Half Day in Chianti with Wine Tasting

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine...

4 to 5 hours Free Cancellation

5.0 (10)

from
$153

Private Biodynamic Wines with lunch in Chianti Classico

The only Experience for true wine lovers. Meeting a producer and their biodynamic approach to wine making. Naturally produced wines by small producers. Genuine Local …More

Florence, Italy

5.0 (5)

Private Biodynamic Wines with lunch in Chianti Classico

The only Experience for true wine lovers. Meeting a producer and their biodynamic approach to wine making. Naturally produced wines by small producers. Genuine Local...

5 hours Hotel pickup offered

5.0 (5)

from
$310

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation …More

Siena, Italy

4.1 (15)

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation...

1 hour 45 minutes Free Cancellation

4.1 (15)

from
$79

Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is …More

San Gimignano, Italy

4.8 (6)

Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is...

1 hour 30 minutes Free Cancellation

4.8 (6)

from
$109

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a …More

Siena, Italy

4.8 (9)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

11 hours Free Cancellation

4.8 (9)

from
$159

Our E-bike tour will lead you through the most famous wine area in Tuscany: Chianti Classico. You will ride amongst Sangiovese vineyards and olive groves …More

Florence, Italy

5.0 (9)

Chianti Classico E-bike Tour

Our E-bike tour will lead you through the most famous wine area in Tuscany: Chianti Classico. You will ride amongst Sangiovese vineyards and olive groves...

8 hours Free Cancellation

5.0 (9)

from
$357

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their …More

Siena, Italy

5.0 (5)

Private Truffle Hunting in Chianti

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their...

5 hours Free Cancellation

5.0 (5)

from
$257

From Florence to Chianti Rufina: Wine Tasting Experience

A journey into the Tuscan tradition though the tasting of 5 white and red wines that will allow you to learn the different facets of …More

Florence, Italy

4.5 (2)

From Florence to Chianti Rufina: Wine Tasting Experience

A journey into the Tuscan tradition though the tasting of 5 white and red wines that will allow you to learn the different facets of...

1 hour 30 minutes Free Cancellation

4.5 (2)

from
$33

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

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia …More

Siena, Italy

5.0 (9)

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia...

4 hours Free Cancellation

5.0 (9)

from
$365

Grape Stomping and Wine Tasting in Tuscany

Areas of viticulture celebrate the end of harvest by crushing grapes under foot. Those scenes of girls with skirts to the knee pounding the grapes …More

Florence, Italy

5.0 (8)

Grape Stomping and Wine Tasting in Tuscany

Areas of viticulture celebrate the end of harvest by crushing grapes under foot. Those scenes of girls with skirts to the knee pounding the grapes...

3 hours

5.0 (8)

from
$207

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in …More

Siena, Italy

4.7 (19)

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in...

7 hours 15 minutes Free Cancellation

4.7 (19)

from
$179

✅ Authentic Tuscan Wine Tasting – Savor 4 to 5 organic wines, including Vernaccia di San Gimignano and Chianti Colli Senesi. ✅ Olive Oil & …More

San Gimignano, Italy

4.9 (9)

Private Wine, Evo oil & Cheese Tasting

✅ Authentic Tuscan Wine Tasting – Savor 4 to 5 organic wines, including Vernaccia di San Gimignano and Chianti Colli Senesi. ✅ Olive Oil &...

1 hour Free Cancellation

4.9 (9)

from
$57

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

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 Pisa, Pasta and Chianti Lovers Wine Experience Livorno Shore Excursion

This tour represent the really life in Tuscany. Visit Pisa and admire the Leaning Tower. Visit the most famous Pasta Factory in the area and …More

Livorno, Italy

5.0 (5)

Private Pisa, Pasta and Chianti Lovers Wine Experience Livorno Shore Excursion

This tour represent the really life in Tuscany. Visit Pisa and admire the Leaning Tower. Visit the most famous Pasta Factory in the area and...

7 hours Free Cancellation

5.0 (5)

from
$96

Florence & Pisa Shore Excursion with Chianti Wine Tasting

Our private shore excursion to Florence, Pisa, and a Chianti winery is an ideal way to see the most popular destinations in Tuscany from the …More

Livorno, Italy

4.8 (5)

Florence & Pisa Shore Excursion with Chianti Wine Tasting

Our private shore excursion to Florence, Pisa, and a Chianti winery is an ideal way to see the most popular destinations in Tuscany from the...

9 hours

4.8 (5)

from
$125

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

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?