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 →

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

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

Wine Tasting and History Guided Day Tour in Chianti

One full day of a beautiful guided sightseeing tour driving through symmetrical vineyards, olive trees, wooded groves, stone farm houses, late Renaissance villas and old …More

Florence, Italy

5.0 (3)

Wine Tasting and History Guided Day Tour in Chianti

One full day of a beautiful guided sightseeing tour driving through symmetrical vineyards, olive trees, wooded groves, stone farm houses, late Renaissance villas and old...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$637

Private Tuscany Day Tour: Siena and Chianti Wine Region from Florence

Art, history, scenic roads, Tuscany wine and food experience all in one day tour from Florence. Traveling in a de luxe Mercedes minivan with english …More

Florence, Italy

5.0 (3)

Private Tuscany Day Tour: Siena and Chianti Wine Region from Florence

Art, history, scenic roads, Tuscany wine and food experience all in one day tour from Florence. Traveling in a de luxe Mercedes minivan with english...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$929

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

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

Private Guided E-bike Tour of San Gimignano with Wine Tasting

Daily bike tour to discover San Gimignano, small walled medieval hill top town. San Gimignano has 13 unique and perfectly preserved tower houses which create …More

Florence, Italy

5.0 (3)

Private Guided E-bike Tour of San Gimignano with Wine Tasting

Daily bike tour to discover San Gimignano, small walled medieval hill top town. San Gimignano has 13 unique and perfectly preserved tower houses which create...

6 hours Free Cancellation

5.0 (3)

from
$228

Golden Grains & Gourmet Pasta Cooking Class

✅ Authentic Tuscan Pasta-Making – Learn time-honored techniques in crafting traditional pasta from milling the grain. ✅ Hands-On Culinary Experience – Engage directly in the …More

San Gimignano, Italy

5.0 (3)

Golden Grains & Gourmet Pasta Cooking Class

✅ Authentic Tuscan Pasta-Making – Learn time-honored techniques in crafting traditional pasta from milling the grain. ✅ Hands-On Culinary Experience – Engage directly in the...

3 hours Free Cancellation

5.0 (3)

from
$316

Private Tuscany Excursion. Florence American Cemetery, Greve in Chianti, Winery

An enjoyng driving tour from Florence through the Tuscan countryside with a fluent english speaking driver who will drive you to visit some attractions of …More

Florence, Italy

5.0 (3)

Private Tuscany Excursion. Florence American Cemetery, Greve in Chianti, Winery

An enjoyng driving tour from Florence through the Tuscan countryside with a fluent english speaking driver who will drive you to visit some attractions of...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$114

Private Wine Tour Top Wineries, Limousine Service, Florence Tours

This Wine Tour of 9 hours on the beautiful Chianti classico area in Tuscany we will visit top wineries and have lunch, cellar tours, wine …More

Florence, Italy

5.0 (3)

Private Wine Tour Top Wineries, Limousine Service, Florence Tours

This Wine Tour of 9 hours on the beautiful Chianti classico area in Tuscany we will visit top wineries and have lunch, cellar tours, wine...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,056

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan …More

Florence, Italy

5.0 (3)

3-Day Tuscany Wine Tour Experience from Florence

Get picked up at your accommodation to experience a three-day full immersion Wine Tour and stay in a private Villa situated in a conventional cosy Tuscan...

3 days

5.0 (3)

from
$2,488

Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: …More

Florence, Italy

5.0 (3)

Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Florence

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer:...

9 hours Hotel pickup offered

5.0 (3)

from
$454

Exclusive Tour from Florence: Siena, Chianti and San Gimignano

This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of …More

Florence, Italy

5.0 (3)

Exclusive Tour from Florence: Siena, Chianti and San Gimignano

This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of...

8 hours Hotel pickup offered

5.0 (3)

from
$879

This exclusive truffle adventure sets itself apart by combining the thrill of truffle hunting with a hands-on Tuscan cooking class, offering a genuine farm-to-table experience …More

San Gimignano, Italy

5.0 (3)

Truffle Hunting & Truffle Cooking Class

This exclusive truffle adventure sets itself apart by combining the thrill of truffle hunting with a hands-on Tuscan cooking class, offering a genuine farm-to-table experience...

4 hours 30 minutes Free Cancellation

5.0 (3)

from
$350

The beauty of the landscape all around and the experience of the tipical lunch in a local winery will be unforgettable …More

Florence, Italy

5.0 (3)

San Gimignano and Chianti tour

The beauty of the landscape all around and the experience of the tipical lunch in a local winery will be unforgettable...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$677

Today we will spend a day in one of the most famous Wine Regions in the World, the Bolgheri DOC where excellent wines are produced. …More

Livorno, Italy

5.0 (3)

Bolgheri Wineries and Tuscany Tour

Today we will spend a day in one of the most famous Wine Regions in the World, the Bolgheri DOC where excellent wines are produced....

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,118

Private Tour from Livorno - Florence with Wine Tasting

Experience the best of Tuscany on this exclusive shore excursion from Livorno. Discover the beauty of Florence, enjoy free time to explore the city, and …More

Livorno, Italy

5.0 (3)

Private Tour from Livorno - Florence with Wine Tasting

Experience the best of Tuscany on this exclusive shore excursion from Livorno. Discover the beauty of Florence, enjoy free time to explore the city, and...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$171

Tuscan Wine & Bruschetta Tasting for Families in San Gimignano

Set in a stunning Tuscan vineyard, this winery tour and tasting offers a perfect mix of authentic flavors, culture, and family-friendly fun. Begin with a …More

San Gimignano, Italy

5.0 (2)

Tuscan Wine & Bruschetta Tasting for Families in San Gimignano

Set in a stunning Tuscan vineyard, this winery tour and tasting offers a perfect mix of authentic flavors, culture, and family-friendly fun. Begin with a...

2 hours Free Cancellation

5.0 (2)

from
$44

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:

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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?