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 Sant’Ambrogio Market Tour & Class with Author Patrizia

Meet your host Patrizia near the Mercato di Sant'Ambrogio. She will guide you through the market, pointing out some of her favorite vendors and products. You …More

Florence, Italy

5.0 (8)

PRIVATE Sant’Ambrogio Market Tour & Class with Author Patrizia

Meet your host Patrizia near the Mercato di Sant'Ambrogio. She will guide you through the market, pointing out some of her favorite vendors and products. You...

4 hours Free Cancellation

5.0 (8)

from
$216

From Livorno: Private Florence & Chianti Tour with Wine Tasting

Embark on a captivating journey through Chianti and Florence, immersing yourself in Renaissance splendor while savoring the finest Chianti wines. Commence your adventure with seamless …More

Livorno, Italy

4.8 (5)

From Livorno: Private Florence & Chianti Tour with Wine Tasting

Embark on a captivating journey through Chianti and Florence, immersing yourself in Renaissance splendor while savoring the finest Chianti wines. Commence your adventure with seamless...

8 hours Hotel pickup offered Free Cancellation

4.8 (5)

from
$216

Private Cooking Class in Tuscany | Hand Made Pasta

You will be welcomed into our country house, immersed in the beauty of the rolling Sienese hills. I am a professional Chef and Sommelier, and …More

Arezzo, Italy

5.0 (1)

Private Cooking Class in Tuscany | Hand Made Pasta

You will be welcomed into our country house, immersed in the beauty of the rolling Sienese hills. I am a professional Chef and Sommelier, and...

4 hours 30 minutes Free Cancellation

5.0 (1)

from
$211

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del …More

Chianciano Terme, Italy

5.0 (58)

2 Hours Visit and Wine Tasting with tastings in Val D'Orcia

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del...

2 hours Free Cancellation

5.0 (58)

from
$80

Private Chianti Classico Wine Tasting Tour in Two Family Wineries

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the …More

Florence, Italy

5.0 (27)

Private Chianti Classico Wine Tasting Tour in Two Family Wineries

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the...

5 hours Hotel pickup offered Free Cancellation

5.0 (27)

from
$184

Livorno Shore Excursion: Pisa, Lucca and wine experience Private Day Trip

Visit Pisa and Lucca with a private tour which really describe the local Italian life. You will be able to reach the most important monuments. …More

Livorno, Italy

5.0 (4)

Livorno Shore Excursion: Pisa, Lucca and wine experience Private Day Trip

Visit Pisa and Lucca with a private tour which really describe the local Italian life. You will be able to reach the most important monuments....

8 hours Free Cancellation

5.0 (4)

from
$107

Pasta Cooking Class in Florence & Wine Tour in Chianti Day Trip

Explore the Heart of Tuscany with an Authentic Culinary and Wine Experience! Calling all food lovers and wine enthusiasts! Embark on a truly unforgettable journey …More

Florence, Italy

5.0 (2)

Pasta Cooking Class in Florence & Wine Tour in Chianti Day Trip

Explore the Heart of Tuscany with an Authentic Culinary and Wine Experience! Calling all food lovers and wine enthusiasts! Embark on a truly unforgettable journey...

8 hours Free Cancellation

5.0 (2)

from
$280

Half-Day Chianti Tour to 2 Wineries with Wine Tastings and Meal

Enjoy 5.5 hrs round trip from Florence in a comfortable 8-seater van to the wine country with our wine expert's commentary about the region. Visit 2 family-owned wineries in the …More

Florence, Italy

4.9 (52)

Half-Day Chianti Tour to 2 Wineries with Wine Tastings and Meal

Enjoy 5.5 hrs round trip from Florence in a comfortable 8-seater van to the wine country with our wine expert's commentary about the region. Visit 2 family-owned wineries in the...

5 hours 30 minutes

4.9 (52)

from
$276

Private Brunello & Nobile Wine Tour with Lunch in Val d'Orcia

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location …More

Arezzo, Italy

4.9 (8)

Private Brunello & Nobile Wine Tour with Lunch in Val d'Orcia

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location...

8 hours Hotel pickup offered Free Cancellation

4.9 (8)

from
$261

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will …More

Siena, Italy

4.6 (10)

Private wine tour of Chianti

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will...

6 to 8 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$325

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in …More

Montecatini Terme, Italy

4.8 (56)

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in...

9 hours Free Cancellation

4.8 (56)

from
$193

Florence Exclusive VIP Wine Tasting Tour with a Special VIP Gift

This exclusive experience invites you to discover the rich winemaking tradition of Tuscany through a personalized tasting. Guided by an expert sommelier, you’ll have the …More

Florence, Italy

5.0 (1)

Florence Exclusive VIP Wine Tasting Tour with a Special VIP Gift

This exclusive experience invites you to discover the rich winemaking tradition of Tuscany through a personalized tasting. Guided by an expert sommelier, you’ll have the...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$132

Small Group Wine Tasting in Tuscany with Vineyard Visit

The tour begins with a trip to the vineyards to learn about and taste the different types of grapes used to make wine. After you’ve …More

Florence, Italy

4.9 (56)

Small Group Wine Tasting in Tuscany with Vineyard Visit

The tour begins with a trip to the vineyards to learn about and taste the different types of grapes used to make wine. After you’ve...

5 hours Free Cancellation

4.9 (56)

from
$154

The only authentic wine tour in Pisa. Visit two real tuscan organic wineries. We are talking about two historical places with two different ways of …More

Pisa, Italy

5.0 (7)

Tuscan Wine Tour in Pisa by van

The only authentic wine tour in Pisa. Visit two real tuscan organic wineries. We are talking about two historical places with two different ways of...

6 hours Free Cancellation

5.0 (7)

from
$183

Private Chianti wine tour leaving from Florence

This private tour will make you discover and enjoy the essence of this land made of breathtaking views, the rolling hill, the small towns, that …More

Florence, Italy

4.9 (26)

Private Chianti wine tour leaving from Florence

This private tour will make you discover and enjoy the essence of this land made of breathtaking views, the rolling hill, the small towns, that...

8 hours Hotel pickup offered Free Cancellation

4.9 (26)

from
$148

Siena, San Gimignano and Chianti Wine Small Group from Lucca

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in …More

Lucca, Italy

4.8 (56)

Siena, San Gimignano and Chianti Wine Small Group from Lucca

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in...

10 hours Free Cancellation

4.8 (56)

from
$193

Are you passionate about food and wine? Then this is the perfect tour for you! If you're looking for an authentic gastronomic experience in Florence, …More

Florence, Italy

5.0 (19)

Food Tour Florence Small Groups

Are you passionate about food and wine? Then this is the perfect tour for you! If you're looking for an authentic gastronomic experience in Florence,...

2 hours 30 minutes Free Cancellation

5.0 (19)

from
$97

Personal Chef - Cooking class at your villa

I’m a Tuscan born based in Val d’Orcia. I love simple, authentic, tasty food. I’ve been cooking for more than 20 years and I’ve managed …More

Arezzo, Italy

5.0 (41)

Personal Chef - Cooking class at your villa

I’m a Tuscan born based in Val d’Orcia. I love simple, authentic, tasty food. I’ve been cooking for more than 20 years and I’ve managed...

3 hours 30 minutes Free Cancellation

5.0 (41)

from
$171

Wine tasting of the great wines of Tuscany with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023, 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022. We can organize the …More

Lucca, Italy

5.0 (3)

Wine tasting of the great wines of Tuscany with sommelier

I am Simone Vergamini, "Best Sommelier of Tuscany 2023, 3rd place at the Best Sommelier of Italy 2018, 2021 and 2022. We can organize the...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$104

Around Tuscany: Carrara Marbles, Pisa & Lucca

Explore the white marble quarries of Carrara, famous for its beauty and used in many works of art, including those by Michelangelo. You will have …More

Florence, Italy

5.0 (1)

Around Tuscany: Carrara Marbles, Pisa & Lucca

Explore the white marble quarries of Carrara, famous for its beauty and used in many works of art, including those by Michelangelo. You will have...

11 hours Free Cancellation

5.0 (1)

from
$207

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?