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 Vespa & Wine Tour, lunch, medieval villages, wine tasting

This all-inclusive small group Vespa moped tour is a great way to discover the beauty of the Tuscan wine countryside and its magic.. …More

Florence, Italy

5.0 (517)

Tuscany Vespa & Wine Tour, lunch, medieval villages, wine tasting

This all-inclusive small group Vespa moped tour is a great way to discover the beauty of the Tuscan wine countryside and its magic.....

6 to 7 hours Free Cancellation

5.0 (517)

from
$228

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the …More

Florence, Italy

4.9 (478)

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the...

7 hours Free Cancellation

4.9 (478)

from
$217

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany …More

Ravenna, Italy

4.9 (428)

Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany...

8 hours Free Cancellation

4.9 (428)

from
$815

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

-friendly and easy going environment -outside patio overlooking the vineyard -opportunity to discuss wine with people from all over the world -personal questions answered in …More

Lucca, Italy

4.8 (394)

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

-friendly and easy going environment -outside patio overlooking the vineyard -opportunity to discuss wine with people from all over the world -personal questions answered in...

1 hour 30 minutes Free Cancellation

4.8 (394)

from
$23

Truffle Hunting Experience with Lunch in San Miniato

Francesca is a true truffle hunter and you will meet her in the family property to discover the magic of the truffle world. …More

Lucca, Italy

4.9 (386)

Truffle Hunting Experience with Lunch in San Miniato

Francesca is a true truffle hunter and you will meet her in the family property to discover the magic of the truffle world....

3 hours

4.9 (386)

from
$230

Siena: A Wine Tour and Tasting Experience

In the hills of the gorgeous Tuscan countryside, just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine …More

Siena, Italy

5.0 (377)

Siena: A Wine Tour and Tasting Experience

In the hills of the gorgeous Tuscan countryside, just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine...

3 hours Free Cancellation

5.0 (377)

from
$97

Florence: Siena & San Gimignano with Dinner in a Boutique Winery

Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a …More

Florence, Italy

4.8 (368)

Florence: Siena & San Gimignano with Dinner in a Boutique Winery

Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a...

9 to 12 hours Free Cancellation

4.8 (368)

from
$123

A Brunello Cooking Class with Vineyards View Winery

Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance …More

Siena, Italy

5.0 (352)

A Brunello Cooking Class with Vineyards View Winery

Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance...

4 hours Free Cancellation

5.0 (352)

from
$296

Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano

When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storybook streets …More

Florence, Italy

4.8 (350)

Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano

When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storybook streets...

9 hours Free Cancellation

4.8 (350)

from
$223

Florence Oltrarno Neighborhood Food & Wine Dine Around

It’s not hard to find good food in Florence, but if you really want to eat as the Florentines do, you need to come along …More

Florence, Italy

4.9 (329)

Florence Oltrarno Neighborhood Food & Wine Dine Around

It’s not hard to find good food in Florence, but if you really want to eat as the Florentines do, you need to come along...

3 hours 30 minutes Free Cancellation

4.9 (329)

from
$126

From Florence: Tuscany Wine Country Day Trip with Vineyard Lunch

See the best of Tuscany in one full day with round-trip transport from Florence, an expert English-speaking guide, and time in three of the region's …More

Florence, Italy

4.9 (326)

From Florence: Tuscany Wine Country Day Trip with Vineyard Lunch

See the best of Tuscany in one full day with round-trip transport from Florence, an expert English-speaking guide, and time in three of the region's...

9 hours Free Cancellation

4.9 (326)

from
$73

Florence VIP Dinner Tour with Florentine Steak and Wine Tasting

Don’t settle for just another dinner. Join us for a premium experience full of all the Florentine flavors you’ve been dreaming of. Eat and drink …More

Florence, Italy

5.0 (326)

Florence VIP Dinner Tour with Florentine Steak and Wine Tasting

Don’t settle for just another dinner. Join us for a premium experience full of all the Florentine flavors you’ve been dreaming of. Eat and drink...

3 hours 30 minutes Free Cancellation

5.0 (326)

from
$165

Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

This day trip is to explore the flavors of the land just south of Florence with its traditions for great wine, olive oil, cheese & …More

Florence, Italy

5.0 (321)

Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

This day trip is to explore the flavors of the land just south of Florence with its traditions for great wine, olive oil, cheese &...

7 hours

5.0 (321)

from
$313

Florence Central Market Food & Wine Tour with Eating Europe

Our Florence Market Food Tour takes you on a culinary journey at the San Lorenzo Market, the heart of Tuscan food traditions. Here you’ll enjoy …More

Florence, Italy

5.0 (300)

Florence Central Market Food & Wine Tour with Eating Europe

Our Florence Market Food Tour takes you on a culinary journey at the San Lorenzo Market, the heart of Tuscan food traditions. Here you’ll enjoy...

3 hours Free Cancellation

5.0 (300)

from
$108

Private Day Trip Siena, San Gimignano and Chianti from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through …More

Florence, Italy

5.0 (271)

Private Day Trip Siena, San Gimignano and Chianti from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (271)

from
$143

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and …More

Siena, Italy

5.0 (263)

Wine Class - Tuscan Classics

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and...

2 hours Free Cancellation

5.0 (263)

from
$68

Tasting Tour in One of The Most Beautiful Cellars in the World

A visit to this Cellar is a voyage in time and history: here is the essence of the sweet Tuscan earth, the wine, that they …More

Montepulciano, Italy

4.9 (245)

Tasting Tour in One of The Most Beautiful Cellars in the World

A visit to this Cellar is a voyage in time and history: here is the essence of the sweet Tuscan earth, the wine, that they...

1 hour Free Cancellation

4.9 (245)

from
$38

Florence Wine Tasting near Ponte Vecchio | Learn Like a Sommelier

Just steps from Ponte Vecchio, this interactive wine tasting is perfect for anyone who wants to experience Italian wine beyond a traditional tasting. Guided by …More

Florence, Italy

4.9 (245)

Florence Wine Tasting near Ponte Vecchio | Learn Like a Sommelier

Just steps from Ponte Vecchio, this interactive wine tasting is perfect for anyone who wants to experience Italian wine beyond a traditional tasting. Guided by...

1 hour Free Cancellation

4.9 (245)

from
$45

Semi Private Deep Wine Chianti and San Gimignano from Florence

This tour is designed to make your Tuscan wine-tasting dreams come true. You'll be able to see all the classic postcard-perfect landscapes of Tuscany while …More

Florence, Italy

4.9 (237)

Semi Private Deep Wine Chianti and San Gimignano from Florence

This tour is designed to make your Tuscan wine-tasting dreams come true. You'll be able to see all the classic postcard-perfect landscapes of Tuscany while...

8 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (237)

from
$239

Chianti Wine Tour with Tastings Semi-Private Experience

Embark on an intimate Tuscany journey: vineyards, olive groves, castles. Immerse in wine senses. Meet Supertuscans, top Tuscan wines. Ride to 3 wineries near Florence. …More

Florence, Italy

5.0 (235)

Chianti Wine Tour with Tastings Semi-Private Experience

Embark on an intimate Tuscany journey: vineyards, olive groves, castles. Immerse in wine senses. Meet Supertuscans, top Tuscan wines. Ride to 3 wineries near Florence....

7 hours Free Cancellation

5.0 (235)

from
$248

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?