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 →

Tuscany Truffle Hunt: A Culinary Adventure

Leave the city behind and enjoy a day in the countryside hunting delectable truffles and enjoying an authentic Tuscan feast. After a ride through the …More

Florence, Italy

5.0 (14)

Tuscany Truffle Hunt: A Culinary Adventure

Leave the city behind and enjoy a day in the countryside hunting delectable truffles and enjoying an authentic Tuscan feast. After a ride through the...

5 hours Hotel pickup offered Free Cancellation

5.0 (14)

from
$346

San Gimignano and Winery Experience with Light Lunch from Pisa

Join our amazing small group tour from Pisa and you'll have the opportunity to tarvel in a confortable minivan or minibus in order to get …More

Pisa, Italy

4.6 (13)

San Gimignano and Winery Experience with Light Lunch from Pisa

Join our amazing small group tour from Pisa and you'll have the opportunity to tarvel in a confortable minivan or minibus in order to get...

7 to 8 hours Free Cancellation

4.6 (13)

from
$169

From Florence PRIVATE:Bolgheri Wine Tour,tasting among the Tuscany coastal hills

Discover with us the unique Italian region where French vines become DOCG Italian fine wine. The sea is visible from the vines and its effect …More

Florence, Italy

5.0 (2)

From Florence PRIVATE:Bolgheri Wine Tour,tasting among the Tuscany coastal hills

Discover with us the unique Italian region where French vines become DOCG Italian fine wine. The sea is visible from the vines and its effect...

10 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$364

Private Tuscan Cooking Class & Wine Tasting from Florence

Enjoy a private Tuscan cooking class set in a family Tuscan home boutique, overlooking the hills of Tuscany. One of the best ways to embrace …More

Florence, Italy

5.0 (3)

Private Tuscan Cooking Class & Wine Tasting from Florence

Enjoy a private Tuscan cooking class set in a family Tuscan home boutique, overlooking the hills of Tuscany. One of the best ways to embrace...

7 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$573

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. • …More

Livorno, Italy

5.0 (10)

From Livorno Port: Private Volterra, San Gimignano & Wine Lunch

Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. •...

8 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$261

Guided tour in San Miniato and wine tasting!

What we propose is a beautiful visit among its famous alleys and buildings, to enjoy this small medieval village that still today smells of history, …More

Lucca, Italy

5.0 (2)

Guided tour in San Miniato and wine tasting!

What we propose is a beautiful visit among its famous alleys and buildings, to enjoy this small medieval village that still today smells of history,...

4 hours Free Cancellation

5.0 (2)

from
$104

Private Chianti Wine Day Experience from Florence with Chauffeur

Enjoy a full-day private Chianti wine experience from Florence, traveling in comfort with your English-speaking chauffeur in a luxury Mercedes-Benz sedan or van. Your driver …More

Florence, Italy

5.0 (2)

Private Chianti Wine Day Experience from Florence with Chauffeur

Enjoy a full-day private Chianti wine experience from Florence, traveling in comfort with your English-speaking chauffeur in a luxury Mercedes-Benz sedan or van. Your driver...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$681

Discover the wonders of Chianti by e-bike, from Montalbano to Leonardo's birthplace. Explore vineyards and taste fine wines on an unforgettable adventure! Take part in …More

Florence, Italy

5.0 (2)

Vinci E-bike tour in Leonardo's Chianti

Discover the wonders of Chianti by e-bike, from Montalbano to Leonardo's birthplace. Explore vineyards and taste fine wines on an unforgettable adventure! Take part in...

5 to 6 hours Free Cancellation

5.0 (2)

from
$183

Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

The best unforgetable tour in Tuscany in order to discover the real life in Tuscany. You will visit the great countryside, you will discover the old …More

Versilia, Italy

5.0 (13)

Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

The best unforgetable tour in Tuscany in order to discover the real life in Tuscany. You will visit the great countryside, you will discover the old...

8 hours Free Cancellation

5.0 (13)

from
$108

PRIVATE Florence Market Tour & Cooking Class in Mirella's Home

This will be a fun filled culinary experience of buying food, talking about food, preparing food and finally eating together with a local culinary expert …More

Florence, Italy

5.0 (12)

PRIVATE Florence Market Tour & Cooking Class in Mirella's Home

This will be a fun filled culinary experience of buying food, talking about food, preparing food and finally eating together with a local culinary expert...

4 hours Free Cancellation

5.0 (12)

from
$329

Brunello Wine Tasting with typical Tuscan Lunch

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views …More

Chianti, Italy

5.0 (3)

Brunello Wine Tasting with typical Tuscan Lunch

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$67

Private Chianti Countryside Vespa Tour from Florence

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL …More

Florence, Italy

5.0 (11)

Private Chianti Countryside Vespa Tour from Florence

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL...

5 hours Free Cancellation

5.0 (11)

from
$455

Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in …More

Siena, Italy

4.3 (57)

Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in...

5 hours 30 minutes Free Cancellation

4.3 (57)

from
$136

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

What’s more Tuscan than a plate of cold-cuts and a glass of wine? After visiting the property and the old cellar, the experience goes on …More

Montepulciano, Italy

5.0 (7)

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

What’s more Tuscan than a plate of cold-cuts and a glass of wine? After visiting the property and the old cellar, the experience goes on...

1 hour 15 minutes Free Cancellation

5.0 (7)

from
$51

For all those who not only want to taste wine but also experience it: At this tasting, you will travel through the vintages of our …More

Chianti, Italy

5.0 (2)

Gourmet Brunello Vertical Tasting

For all those who not only want to taste wine but also experience it: At this tasting, you will travel through the vintages of our...

2 hours 30 minutes Free Cancellation

5.0 (2)

from
$92

Tasty Tuscany—Olive Oil Mill & Winery Tastings—max 8 pp

Discover the culinary treasures of Tuscany on this intimate wine tour, limited to just 8 guests. Wander through three organic farms, including an olive mill …More

Florence, Italy

5.0 (9)

Tasty Tuscany—Olive Oil Mill & Winery Tastings—max 8 pp

Discover the culinary treasures of Tuscany on this intimate wine tour, limited to just 8 guests. Wander through three organic farms, including an olive mill...

7 hours

5.0 (9)

from
$284

Full-Day Tuscany Castles Tour with Wine Tasting from Florence

This tour takes you to visit one of the oldest wine regions of Chianti where you can enjoy the beauty of ancient castles and villa. …More

Florence, Italy

5.0 (50)

Full-Day Tuscany Castles Tour with Wine Tasting from Florence

This tour takes you to visit one of the oldest wine regions of Chianti where you can enjoy the beauty of ancient castles and villa....

6 to 7 hours

5.0 (50)

from
$314

Private Tour- Chianti By Minivan At Sunset

Escape the heat and bustle of the city for the renowned beauty of the Tuscan countryside in the most famous wine region of Italy – …More

Florence, Italy

4.8 (4)

Private Tour- Chianti By Minivan At Sunset

Escape the heat and bustle of the city for the renowned beauty of the Tuscan countryside in the most famous wine region of Italy –...

5 hours Hotel pickup offered Free Cancellation

4.8 (4)

from
$142

Volterra and San Gimignano: a taste of medieval Tuscany!

Hi ! About 90% of tourists usually head straight to Pisa and Florence – and yes, they’re amazing – but this tour offers something a …More

Pisa, Italy

5.0 (23)

Volterra and San Gimignano: a taste of medieval Tuscany!

Hi ! About 90% of tourists usually head straight to Pisa and Florence – and yes, they’re amazing – but this tour offers something a...

9 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$1,010

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive …More

Siena, Italy

5.0 (41)

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive...

8 hours Hotel pickup offered Free Cancellation

5.0 (41)

from
$795

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?