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 →

Let’s explore the so-called Colline Lucchesi and Montecarlo wine areas. This area is known not only for typical Tuscan Sangiovese and Trebbiano grapes, but also …More

Versilia, Italy

5.0 (2)

Wine tour and lunch in Lucca area

Let’s explore the so-called Colline Lucchesi and Montecarlo wine areas. This area is known not only for typical Tuscan Sangiovese and Trebbiano grapes, but also...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$402

Private driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show …More

Florence, Italy

5.0 (2)

Private driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$930

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

Siena, Italy

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$272

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

Siena, Italy

5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$339

Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on …More

San Gimignano, Italy

5.0 (2)

Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$86

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods …More

San Gimignano, Italy

5.0 (2)

Private wine & Evo Oils Tasting with Vegetarian Meal

Take a break in a Tuscan atmosphere with a vegetarian lunch or dinner. The experience will start with a detailed introduction to the agricultural methods...

90 to 120 minutes Free Cancellation

5.0 (2)

from
$78

✅ Saffron-Themed Tuscan Lunch – Enjoy a four-course meal featuring San Gimignano’s prized saffron. ✅ Exclusive Wine Pairing – Each dish is complemented by a …More

San Gimignano, Italy

5.0 (2)

Private Wine & Evo oil tasting with Saffron Meal

✅ Saffron-Themed Tuscan Lunch – Enjoy a four-course meal featuring San Gimignano’s prized saffron. ✅ Exclusive Wine Pairing – Each dish is complemented by a...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$98

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and …More

Livorno, Italy

5.0 (2)

Bolgheri Wine Tour from Livorno

A full day in the Bolgheri DOC area, one of the most famous wine regions in our country. Today we will visit 2 wineries and...

7 to 8 hours Free Cancellation

5.0 (2)

from
$1,004

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

Lucca, Italy

5.0 (2)

Bolgheri Wine Tour from Lucca

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

8 hours Hotel pickup offered

5.0 (2)

from
$1,004

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the …More

Florence, Italy

5.0 (2)

Private Day Trip to Montalcino and Montepulciano from Florence

Embark on a 9-hour private tour from Florence to the Tuscan Brunello vineyards, the perfect excursion for the discerning traveler and wine enthusiast. Travel from the...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,365

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage. …More

Florence, Italy

5.0 (2)

Private driver from Florence: Siena, San Gimignano, Pisa 12 hours

A long intense day where we will see the main city of Tuscany: Pisa, San Gimignano & Siena. Learn about it's history, culture and heritage....

12 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,630

Meet the king of the territory: Brunello di Montalcino

Original full day tour that will lead you into the most charming wine cellars which produce the king of Italian wines: Brunello di Montalcino. An experience among …More

Chianti, Italy

5.0 (2)

Meet the king of the territory: Brunello di Montalcino

Original full day tour that will lead you into the most charming wine cellars which produce the king of Italian wines: Brunello di Montalcino. An experience among...

7 hours

5.0 (2)

from
$400

Truffle Adventure Cooking Class & tasting

Unlike standard cooking classes, our Truffle Cooking Experience is an exclusive, hands-on journey guided by our chef and sommelier in a private Tuscan setting. Before …More

San Gimignano, Italy

5.0 (2)

Truffle Adventure Cooking Class & tasting

Unlike standard cooking classes, our Truffle Cooking Experience is an exclusive, hands-on journey guided by our chef and sommelier in a private Tuscan setting. Before...

3 hours Free Cancellation

5.0 (2)

from
$316

Private Vintage Fiat 500 Tour in Chianti From Florence

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

Florence, Italy

5.0 (2)

Private Vintage Fiat 500 Tour in Chianti From Florence

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$323

PRIVATE Florence Cooking Class & Wine Tasting with Chef Antonella

Enjoy a private and authentic cooking class in a local Florence home with your host Antonella and her family. This is a perfect experience for …More

Florence, Italy

5.0 (2)

PRIVATE Florence Cooking Class & Wine Tasting with Chef Antonella

Enjoy a private and authentic cooking class in a local Florence home with your host Antonella and her family. This is a perfect experience for...

3 hours 30 minutes Free Cancellation

5.0 (2)

from
$184

Nestled in the heart of Tuscany, the estate offers a glimpse into the traditional life of the Italian countryside. Amongst the rolling hills, majestic landscape …More

Arezzo, Italy

5.0 (2)

Tour & Tasting

Nestled in the heart of Tuscany, the estate offers a glimpse into the traditional life of the Italian countryside. Amongst the rolling hills, majestic landscape...

2 hours Free Cancellation

5.0 (2)

from
$34

Private Tuscany Tour from Florence Including the Leaning Tower of Pisa and Sangimignano

Take a private amazing day trip through the hills of the Tuscan countryside. Stop to visit the Leaning Tower of Pisa and Sangimignano, the most …More

Florence, Italy

5.0 (2)

Private Tuscany Tour from Florence Including the Leaning Tower of Pisa and Sangimignano

Take a private amazing day trip through the hills of the Tuscan countryside. Stop to visit the Leaning Tower of Pisa and Sangimignano, the most...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,111

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and …More

Siena, Italy

5.0 (2)

By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and...

5 hours 20 minutes Free Cancellation

5.0 (2)

from
$176

Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit …More

Arezzo, Italy

5.0 (2)

Around Lucignano Private ebike tour and Cooking Class

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit...

4 to 6 hours Free Cancellation

5.0 (2)

from
$616

I've been making cooking class for foreigners coming from all over the word for more than 5 years in Pisa. I find it so exciting …More

Pisa, Italy

5.0 (2)

Pisa Private Cooking Class

I've been making cooking class for foreigners coming from all over the word for more than 5 years in Pisa. I find it so exciting...

1 day 3 hours Free Cancellation

5.0 (2)

from
$102

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?