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, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore …More

Siena, Italy

4.6 (181)

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore...

11 hours Free Cancellation

4.6 (181)

from
$90

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

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
$125

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 (367)

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 (367)

from
$122

Siena walking tour with lunch & Chianti wine

I will take you for a wonderful walk and show you historical Cafes, local deli, mediaeval alleys, secret medieval caves and the "the oldest bank …More

Siena, Italy

4.8 (99)

Siena walking tour with lunch & Chianti wine

I will take you for a wonderful walk and show you historical Cafes, local deli, mediaeval alleys, secret medieval caves and the "the oldest bank...

2 hours 30 minutes Free Cancellation

4.8 (99)

from
$98

Florence: Private Half-Day Chianti Tour and Wine Tasting Optional

An unforgettable half day chauffeur-driven tour in the heart of Chianti, far from the hustle and bustle of Florence. Let your personal chauffeur do all the …More

Florence, Italy

4.8 (48)

Florence: Private Half-Day Chianti Tour and Wine Tasting Optional

An unforgettable half day chauffeur-driven tour in the heart of Chianti, far from the hustle and bustle of Florence. Let your personal chauffeur do all the...

5 hours Hotel pickup offered Free Cancellation

4.8 (48)

from
$98

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

You have dreamed of a romantic Italian getaway. Be ready to make that dream a reality with this 4+ hour Fiat 500 tour from Florence …More

Florence, Italy

4.9 (664)

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

You have dreamed of a romantic Italian getaway. Be ready to make that dream a reality with this 4+ hour Fiat 500 tour from Florence...

4 hours Free Cancellation

4.9 (664)

from
$139

Exclusive Wine Tasting in the Historic Center of Siena

Explore the fascinating world of Tuscan sparkling wines with us! Book our unique experience now and discover what makes our business so special. During the …More

Siena, Italy

5.0 (41)

Exclusive Wine Tasting in the Historic Center of Siena

Explore the fascinating world of Tuscan sparkling wines with us! Book our unique experience now and discover what makes our business so special. During the...

1 hour Free Cancellation

5.0 (41)

from
$40

Florence Wine Tasting Experience with Seven Types of Tuscan Wine

This experience offers a unique opportunity to embark on a journey through the heart of Tuscany's winemaking tradition. With seven carefully selected wines, you will …More

Florence, Italy

5.0 (56)

Florence Wine Tasting Experience with Seven Types of Tuscan Wine

This experience offers a unique opportunity to embark on a journey through the heart of Tuscany's winemaking tradition. With seven carefully selected wines, you will...

1 hour 30 minutes Free Cancellation

5.0 (56)

from
$67

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

PRIVATE Tuscan Pasta Class in Florence at Chef Cinzia's Home

For a truly memorable meal and culinary experience in Florence, join a local chef in preparing an authentic Italian menu of fresh pasta and other …More

Florence, Italy

5.0 (57)

PRIVATE Tuscan Pasta Class in Florence at Chef Cinzia's Home

For a truly memorable meal and culinary experience in Florence, join a local chef in preparing an authentic Italian menu of fresh pasta and other...

3 hours Free Cancellation

5.0 (57)

from
$169

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

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
$247

Bolgheri: Premium Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and wine-tasting for a 90 minutes experience tour. Nestled 3mi (5 km) from the village center of Bolgheri, you're …More

Livorno, Italy

4.9 (53)

Bolgheri: Premium Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and wine-tasting for a 90 minutes experience tour. Nestled 3mi (5 km) from the village center of Bolgheri, you're...

1 hour 15 minutes Free Cancellation

4.9 (53)

from
$50

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

This is our best-selling tour that has made us famous among the public. It’s the perfect balance between cycling, admiring beautiful landscapes and tasting the …More

Florence, Italy

5.0 (1,310)

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

This is our best-selling tour that has made us famous among the public. It’s the perfect balance between cycling, admiring beautiful landscapes and tasting the...

6 hours Free Cancellation

5.0 (1,310)

from
$138

Small Group Wine Tour & San Gimignano Visit

Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards and cellar of an organic …More

Florence, Italy

4.9 (808)

Small Group Wine Tour & San Gimignano Visit

Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour vineyards and cellar of an organic...

8 hours Free Cancellation

4.9 (808)

from
$217

Tasting in a Tuscan Vineyard with transfer from Lucca

The only authentic aperitif in the vineyard of Tuscany. It is a story of passion, of farmers, and historical places: a winery off the beaten …More

Lucca, Italy

4.9 (122)

Tasting in a Tuscan Vineyard with transfer from Lucca

The only authentic aperitif in the vineyard of Tuscany. It is a story of passion, of farmers, and historical places: a winery off the beaten...

3 hours Free Cancellation

4.9 (122)

from
$102

Montefioralle Winery - Tour and Wine Tasting in Chianti

Montefioralle Winery is very small family-run winery where you can enjoy the outstanding view of the old village of Montefioralle Generally, it is always possible …More

Chianti, Italy

4.5 (66)

Montefioralle Winery - Tour and Wine Tasting in Chianti

Montefioralle Winery is very small family-run winery where you can enjoy the outstanding view of the old village of Montefioralle Generally, it is always possible...

1 hour 15 minutes Free Cancellation

4.5 (66)

from
$40

Cooking, Dinner & Live Opera in the countryside

Much more than a cooking course, it will be a unique experience. Sight, smell, hearing ... in this path the 5 senses will be involved, …More

Chianti, Italy

4.9 (43)

Cooking, Dinner & Live Opera in the countryside

Much more than a cooking course, it will be a unique experience. Sight, smell, hearing ... in this path the 5 senses will be involved,...

3 hours 30 minutes Free Cancellation

4.9 (43)

from
$207

Tuscan Cooking Class - Traditional 5 course menù

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by …More

Montepulciano, Italy

5.0 (120)

Tuscan Cooking Class - Traditional 5 course menù

Kitchen has always been the fulcrum of this home, where my family is living since more than 7 generations. I have always been fascinated by...

5 hours Free Cancellation

5.0 (120)

from
$304

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?