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 Guided Tour to Pisa and local Wine Farm from Livorno port

If you are looking for a nice experience far away by the crowd you are in the right page, our private tour is made even …More

Livorno, Italy

5.0 (23)

Private Guided Tour to Pisa and local Wine Farm from Livorno port

If you are looking for a nice experience far away by the crowd you are in the right page, our private tour is made even...

8 hours Free Cancellation

5.0 (23)

from
$902

Pisa Pasta Cooking Class (Private Experience)

Join a hands-on pasta cooking class near Pisa, where you’ll learn how to make fresh Italian pasta from scratch using traditional techniques passed down through …More

5.0 (36)

Pisa Pasta Cooking Class (Private Experience)

Join a hands-on pasta cooking class near Pisa, where you’ll learn how to make fresh Italian pasta from scratch using traditional techniques passed down through...

3 hours 30 minutes Free Cancellation

5.0 (36)

from
$148

Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring …More

Siena, Italy

4.7 (36)

Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring...

1 hour 30 minutes Free Cancellation

4.7 (36)

from
$57

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
$271

Montepulciano: Cinta Senese Farm Tour, Food Tasting & wine

Immerse yourself in the heart of the Tuscan countryside with a visit to a traditional Cinta Senese farm near Montepulciano. Start with a walk through …More

Montepulciano, Italy

5.0 (23)

Montepulciano: Cinta Senese Farm Tour, Food Tasting & wine

Immerse yourself in the heart of the Tuscan countryside with a visit to a traditional Cinta Senese farm near Montepulciano. Start with a walk through...

2 hours Free Cancellation

5.0 (23)

from
$66

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
$170

Become a local of Lucca by experiencing the traditional rustic flavours of Tuscany on a charming walking tour. Taste original and quality food, wines and …More

Lucca, Italy

5.0 (23)

2Italia Lucca Food Tour

Become a local of Lucca by experiencing the traditional rustic flavours of Tuscany on a charming walking tour. Taste original and quality food, wines and...

3 hours 30 minutes Free Cancellation

5.0 (23)

from
$136

Organic Wine Tasting with Panoramic Chianti Classico Views

Exceptional Organic Wines: Sip your way through a guided tasting of our acclaimed organic Chianti Classico and Supertuscan wines, hosted by our friendly wine experts. …More

San Gimignano, Italy

4.8 (28)

Organic Wine Tasting with Panoramic Chianti Classico Views

Exceptional Organic Wines: Sip your way through a guided tasting of our acclaimed organic Chianti Classico and Supertuscan wines, hosted by our friendly wine experts....

1 hour 15 minutes Free Cancellation

4.8 (28)

from
$40

Private Tour to Siena and San Gimignano with Wine Tasting & Lunch

Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover …More

Florence, Italy

4.8 (20)

Private Tour to Siena and San Gimignano with Wine Tasting & Lunch

Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover...

8 hours Hotel pickup offered Free Cancellation

4.8 (20)

from
$563

Chianti Wineries Tour, Medieval Villages, Lunch, Wine Tastings

Our small group Chianti Wine Tour is a great way to discover the Beauty of the Tuscan wine countryside, meet with local wine makers and …More

Florence, Italy

5.0 (128)

Chianti Wineries Tour, Medieval Villages, Lunch, Wine Tastings

Our small group Chianti Wine Tour is a great way to discover the Beauty of the Tuscan wine countryside, meet with local wine makers and...

8 hours Free Cancellation

5.0 (128)

from
$205

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
$1,249

Urban Bikery wants to pay tribute to the prestigious territory in which it has its headquarters by organizing a 100% eco-sustainable wine tour in an …More

Montepulciano, Italy

4.9 (159)

Wine Tour Ebike Experience

Urban Bikery wants to pay tribute to the prestigious territory in which it has its headquarters by organizing a 100% eco-sustainable wine tour in an...

5 hours Free Cancellation

4.9 (159)

from
$183

Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

Discover the Podere Montale Winery with an exclusive experience, guided by an expert wine connoisseur. Visit the vineyard where Sangiovese grapes grow, then continuing to …More

4.9 (29)

Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

Discover the Podere Montale Winery with an exclusive experience, guided by an expert wine connoisseur. Visit the vineyard where Sangiovese grapes grow, then continuing to...

2 hours Free Cancellation

4.9 (29)

from
$68

Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard

Escape the city chaos and get a true taste of Italy's famous Chianti Region. Plunge yourself into the unique charm of this picture postcard landscape, …More

Florence, Italy

4.7 (56)

Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard

Escape the city chaos and get a true taste of Italy's famous Chianti Region. Plunge yourself into the unique charm of this picture postcard landscape,...

6 hours 30 minutes Free Cancellation

4.7 (56)

from
$137

Florence Great Chianti Wine and Olive Oil Trail with Lunch

Discover Tuscany’s wine paradise on a tour from Florence, crafted by Towns of Italy. Travel in a luxury Mercedes minivan through the Chianti Classico region, …More

Florence, Italy

4.9 (25)

Florence Great Chianti Wine and Olive Oil Trail with Lunch

Discover Tuscany’s wine paradise on a tour from Florence, crafted by Towns of Italy. Travel in a luxury Mercedes minivan through the Chianti Classico region,...

7 hours Free Cancellation

4.9 (25)

from
$101

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those …More

Florence, Italy

5.0 (31)

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$172

Guided Wine Walk in Florence with 3 Wine Pairing and Food Tasting

A Wine Tasting Experience designed for those who appreciate fine wines and wish to deepen their knowledge in an intimate and engaging setting: - Small …More

Florence, Italy

5.0 (21)

Guided Wine Walk in Florence with 3 Wine Pairing and Food Tasting

A Wine Tasting Experience designed for those who appreciate fine wines and wish to deepen their knowledge in an intimate and engaging setting: - Small...

3 hours Free Cancellation

5.0 (21)

from
$79

Chianti and San Gimignano - 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward the heart of Chianti Classico. Experience a 1-day exciting trip in …More

Florence, Italy

4.9 (85)

Chianti and San Gimignano - 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward the heart of Chianti Classico. Experience a 1-day exciting trip in...

6 to 8 hours Free Cancellation

4.9 (85)

from
$261

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This …More

Florence, Italy

5.0 (18)

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This...

10 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$331

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?