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 Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

Siena, Italy

5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$340

Wine lovers experience in Montepulciano: full day

Certo, ecco la traduzione in inglese: This tour is designed for true wine lovers who wish to discover Montepulciano through its wines and wineries, enjoying …More

Montepulciano, Italy

4.4 (5)

Wine lovers experience in Montepulciano: full day

Certo, ecco la traduzione in inglese: This tour is designed for true wine lovers who wish to discover Montepulciano through its wines and wineries, enjoying...

6 hours Free Cancellation

4.4 (5)

from
$399

Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on …More

San Gimignano, Italy

5.0 (2)

Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$86

San Gimignano and Siena Private Wine Tasting Tour with Lunch

This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the …More

Lucca, Italy

5.0 (4)

San Gimignano and Siena Private Wine Tasting Tour with Lunch

This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the...

9 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$227

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

Chianti e-bike tour from Florence with wine tasting

Bike tour to discover the hills around Florence, the beautiful area of Chianti Colli Fiorentini and Chianti Classico. The tour start from San Donato, small …More

San Gimignano, Italy

5.0 (3)

Chianti e-bike tour from Florence with wine tasting

Bike tour to discover the hills around Florence, the beautiful area of Chianti Colli Fiorentini and Chianti Classico. The tour start from San Donato, small...

6 hours Free Cancellation

5.0 (3)

from
$217

Chianti Region and San Gimignano including wine tasting and light lunch

Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you …More

Florence, Italy

5.0 (3)

Chianti Region and San Gimignano including wine tasting and light lunch

Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you...

8 to 9 hours

5.0 (3)

from
$362

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods …More

San Gimignano, Italy

5.0 (2)

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods...

90 to 120 minutes Free Cancellation

5.0 (2)

from
$78

Semi-Private Chianti Wine Tour with Dinner in Tuscany Vineyard

Small-group tour limited to 25 travel companions. Enjoy the Tuscan flavors and natural beauty of the Chianti region. Escape from the city chaos and immerse …More

Florence, Italy

5.0 (3)

Semi-Private Chianti Wine Tour with Dinner in Tuscany Vineyard

Small-group tour limited to 25 travel companions. Enjoy the Tuscan flavors and natural beauty of the Chianti region. Escape from the city chaos and immerse...

6 hours 30 minutes Free Cancellation

5.0 (3)

from
$204

Chianti tasting Arezzo city center Wine & Oil

We offer an excellent tasting of typical products of the area that, usually, one would expect to find in the boundless countryside, the peculiarity of …More

Arezzo, Italy

4.3 (9)

Chianti tasting Arezzo city center Wine & Oil

We offer an excellent tasting of typical products of the area that, usually, one would expect to find in the boundless countryside, the peculiarity of...

1 hour 30 minutes Free Cancellation

4.3 (9)

from
$29

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in …More

San Gimignano, Italy

5.0 (2)

San Gimignano: Vineyard and Cellar Tour with Wine Tasting

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$52

Private Wine Tour in Tuscany Florence Limo Service English driver

A 6 hours wine tour with an expert driver English speaking that will drive you to see the best that from the countryside of Tuscany …More

Florence, Italy

5.0 (4)

Private Wine Tour in Tuscany Florence Limo Service English driver

A 6 hours wine tour with an expert driver English speaking that will drive you to see the best that from the countryside of Tuscany...

6 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$953

✅ Saffron-Themed Tuscan Lunch – Enjoy a four-course meal featuring San Gimignano’s prized saffron. ✅ Exclusive Wine Pairing – Each dish is complemented by a …More

San Gimignano, Italy

5.0 (2)

Private Wine & Evo oil tasting with Saffron Meal

✅ Saffron-Themed Tuscan Lunch – Enjoy a four-course meal featuring San Gimignano’s prized saffron. ✅ Exclusive Wine Pairing – Each dish is complemented by a...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$98

Wine Tasting and Visit to the Vineyard and Cellar in Trequanda

Visit to organic vineyards and cellars with itinerant tasting, sensory experience in the immersive room. Thanks to a very expert guide, you will learn how …More

4.8 (4)

Wine Tasting and Visit to the Vineyard and Cellar in Trequanda

Visit to organic vineyards and cellars with itinerant tasting, sensory experience in the immersive room. Thanks to a very expert guide, you will learn how...

1 hour 30 minutes Free Cancellation

4.8 (4)

from
$38

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and …More

Livorno, Italy

5.0 (2)

Bolgheri Wine Tour from Livorno

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and...

7 to 8 hours Free Cancellation

5.0 (2)

from
$1,004

Experience the magic of Tuscany with our intimate Small Group Sunset Chianti Wine Tour. Embark on a journey that will tantalize your senses as you …More

Florence, Italy

5.0 (4)

Sunset VIP Chianti wine tour

Experience the magic of Tuscany with our intimate Small Group Sunset Chianti Wine Tour. Embark on a journey that will tantalize your senses as you...

4 to 5 hours Free Cancellation

5.0 (4)

from
$402

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully …More

Siena, Italy

5.0 (3)

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$228

Today we will take you to the famous Wine Region of Bolgheri where some of the best wines in the World are produced. We will …More

Lucca, Italy

5.0 (2)

Bolgheri Wine Tour from Lucca

Today we will take you to the famous Wine Region of Bolgheri where some of the best wines in the World are produced. We will...

8 hours Hotel pickup offered

5.0 (2)

from
$1,004

Walking Tour and Wine Experience in Florence

A unique walk around Florence in the company of our history and art experts. You will see the most beautiful masterpieces of the city and …More

Florence, Italy

5.0 (3)

Walking Tour and Wine Experience in Florence

A unique walk around Florence in the company of our history and art experts. You will see the most beautiful masterpieces of the city and...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$147

Biodynamic Wine Tasting with Producer in Vinci

We offer an experience, not just a tasting. First of all we are biodynamic wine producers. We therefore produce very special artisanal wines. We want …More

Florence, Italy

5.0 (3)

Biodynamic Wine Tasting with Producer in Vinci

We offer an experience, not just a tasting. First of all we are biodynamic wine producers. We therefore produce very special artisanal wines. We want...

1 hour Free Cancellation

5.0 (3)

from
$39

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?