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 →

Small Group Chianti Wine Tour with a Somm

Perfect for wine lovers and cultural enthusiasts alike, this Tour offers an authentic taste of Tuscany’s rich winemaking legacy with a Certified Sommelier. Beyond the …More

Florence, Italy

5.0 (17)

Small Group Chianti Wine Tour with a Somm

Perfect for wine lovers and cultural enthusiasts alike, this Tour offers an authentic taste of Tuscany’s rich winemaking legacy with a Certified Sommelier. Beyond the...

8 hours Free Cancellation

5.0 (17)

from
$239

Half-day Chianti Classico Wine tour from Florence - Small Group

A perfect afternoon to discover the Tuscan countryside Terrific scenery of the Chianti Classico wine region Perfect tour for wine lovers -Sample several types of …More

Florence, Italy

5.0 (17)

Half-day Chianti Classico Wine tour from Florence - Small Group

A perfect afternoon to discover the Tuscan countryside Terrific scenery of the Chianti Classico wine region Perfect tour for wine lovers -Sample several types of...

5 hours Free Cancellation

5.0 (17)

from
$171

Private Wine Tasting at Your Villa in Umbria & Tuscany

Imagine spending a relaxing evening with friends or family, surrounded by the beautiful landscapes of Umbria or Tuscany, while a professional local sommelier comes directly …More

Arezzo, Italy

5.0 (17)

Private Wine Tasting at Your Villa in Umbria & Tuscany

Imagine spending a relaxing evening with friends or family, surrounded by the beautiful landscapes of Umbria or Tuscany, while a professional local sommelier comes directly...

2 hours Free Cancellation

5.0 (17)

from
$46

Emanuele, a licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best …More

Siena, Italy

5.0 (17)

Discover Chianti Classico Wines

Emanuele, a licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best...

8 hours

5.0 (17)

from
$281

Florence Walking Tour Explore Renaissance Gems and Wine Window

Discover the essence of Florence on this intimate walking tour led by a certified local guide. Journey through the historic center, starting in the San …More

Florence, Italy

5.0 (17)

Florence Walking Tour Explore Renaissance Gems and Wine Window

Discover the essence of Florence on this intimate walking tour led by a certified local guide. Journey through the historic center, starting in the San...

2 hours Free Cancellation

5.0 (17)

from
$79

Brunello di Montalcino Wine Tour with 2 Wineries & Lunch at Farm

Discover the famous Brunello di Montalcino, one of the most renowned wines worldwide. Travel to the land of Brunello, passing along one of Tuscany’s most …More

Florence, Italy

5.0 (16)

Brunello di Montalcino Wine Tour with 2 Wineries & Lunch at Farm

Discover the famous Brunello di Montalcino, one of the most renowned wines worldwide. Travel to the land of Brunello, passing along one of Tuscany’s most...

9 hours Free Cancellation

5.0 (16)

from
$236

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

Revel in Tuscany’s wine country and hilltop towns on this Privateday trip from Florence. Traveling by luxury minivan with an expert driver-escort, explore the idyllic …More

Florence, Italy

4.8 (16)

Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch

Revel in Tuscany’s wine country and hilltop towns on this Privateday trip from Florence. Traveling by luxury minivan with an expert driver-escort, explore the idyllic...

9 hours Hotel pickup offered Free Cancellation

4.8 (16)

from
$288

Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

Spend a day exploring the wine region of the Val d'Orcia (Orcia Valley) with this full-day private tour from Florence. With your private group of …More

Florence, Italy

4.9 (16)

Private Tour: Orcia Valley to Montalcino and Montepulciano with Brunello Wine Tasting

Spend a day exploring the wine region of the Val d'Orcia (Orcia Valley) with this full-day private tour from Florence. With your private group of...

9 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$1,258

From Florence:Tuscany Tuk Tuk with Lunch, Wine & San Gimignano

Experience the beauty of Tuscany on a private tuk-tuk tour through the Chianti countryside! Depart from Florence by shared bus/van, then enjoy an exclusive ride …More

Florence, Italy

5.0 (16)

From Florence:Tuscany Tuk Tuk with Lunch, Wine & San Gimignano

Experience the beauty of Tuscany on a private tuk-tuk tour through the Chianti countryside! Depart from Florence by shared bus/van, then enjoy an exclusive ride...

7 hours Free Cancellation

5.0 (16)

from
$318

Montepulciano, Montalcino, Pienza from Florence

The Val d ‘Orcia: a beautiful area in southern Tuscany, declared Unesco world heritage thanks to its incredible landscapes that make this area one of …More

Florence, Italy

4.9 (16)

Montepulciano, Montalcino, Pienza from Florence

The Val d ‘Orcia: a beautiful area in southern Tuscany, declared Unesco world heritage thanks to its incredible landscapes that make this area one of...

9 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$153

Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you …More

San Gimignano, Italy

4.8 (16)

Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you...

1 hour 30 minutes Free Cancellation

4.8 (16)

from
$109

From Rome: Day Trip to Tuscany & Siena with lunch & Wine Tasting

Discover the wonders of Tuscany on this full-day trip from Rome. Visit the Medieval towns of Siena, San Gimignano, and Monteriggioni, learn about Tuscany's rich-history, …More

Florence, Italy

5.0 (15)

From Rome: Day Trip to Tuscany & Siena with lunch & Wine Tasting

Discover the wonders of Tuscany on this full-day trip from Rome. Visit the Medieval towns of Siena, San Gimignano, and Monteriggioni, learn about Tuscany's rich-history,...

14 hours Free Cancellation

5.0 (15)

from
$283

Chianti Wine Tour from Florence with 3 Wineries and Tuscan Lunch

This full-day tour in the Chianti Classico region offers the perfect opportunity to discover the wonders of this renowned wine area. The first area we …More

Florence, Italy

5.0 (15)

Chianti Wine Tour from Florence with 3 Wineries and Tuscan Lunch

This full-day tour in the Chianti Classico region offers the perfect opportunity to discover the wonders of this renowned wine area. The first area we...

7 hours Free Cancellation

5.0 (15)

from
$226

Discovering the Bolgheri vineyards and tasting local products

Immerse yourself in our exclusive location to taste excellent wines that convey all the passion we have. There will be a trained person who will …More

Livorno, Italy

4.8 (15)

Discovering the Bolgheri vineyards and tasting local products

Immerse yourself in our exclusive location to taste excellent wines that convey all the passion we have. There will be a trained person who will...

1 hour 30 minutes Free Cancellation

4.8 (15)

from
$32

Montepulciano Pienza Montalcino Tour from Florence

Today we will take you to the famous Wine Region of Orcia Valley where some of the best wines in the World are produced. We …More

Florence, Italy

4.9 (15)

Montepulciano Pienza Montalcino Tour from Florence

Today we will take you to the famous Wine Region of Orcia Valley where some of the best wines in the World are produced. We...

9 hours Hotel pickup offered Free Cancellation

4.9 (15)

from
$1,124

Montalcino: Brunello Wine Tasting & Tuscan Lunch

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, …More

Chianti, Italy

4.9 (14)

Montalcino: Brunello Wine Tasting & Tuscan Lunch

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci,...

1 hour 30 minutes Free Cancellation

4.9 (14)

from
$111

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
$347

Private Chianti Wine Tasting from Florence, Half Day Experience

If you are a wine-lover coming to Italy, this Half Day Tuscany Wine Tasting is a must. This experience takes you into the Chianti hills, …More

Florence, Italy

5.0 (14)

Private Chianti Wine Tasting from Florence, Half Day Experience

If you are a wine-lover coming to Italy, this Half Day Tuscany Wine Tasting is a must. This experience takes you into the Chianti hills,...

6 hours Hotel pickup offered Free Cancellation

5.0 (14)

from
$408

4 Wines Tasting with 2 Tuscan Cheeses & Tour at the winery

We have a large wine-tasting room dedicated, where the guests can sit at tables. They will taste 4 wines (2 IGT Toscana Wines, 1 Chianti …More

Florence, Italy

5.0 (14)

4 Wines Tasting with 2 Tuscan Cheeses & Tour at the winery

We have a large wine-tasting room dedicated, where the guests can sit at tables. They will taste 4 wines (2 IGT Toscana Wines, 1 Chianti...

1 hour 40 minutes

5.0 (14)

from
$42

Private tasting of organic wines in the cellar in Arezzo

Our cellar has a century of history, it is located in the urban fabric a short distance from the center of Arezzo, reachable by car …More

Arezzo, Italy

5.0 (14)

Private tasting of organic wines in the cellar in Arezzo

Our cellar has a century of history, it is located in the urban fabric a short distance from the center of Arezzo, reachable by car...

1 hour 30 minutes Free Cancellation

5.0 (14)

from
$29

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:

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?