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 wine, Extra Virgin Olive Oils & Cheese Tasting

Indulge in the authentic flavors of Tuscany with this exclusive wine, olive oil & balsamic vinegar tasting experience just minutes from the heart of San …More

San Gimignano, Italy

4.0 (9)

Private wine, Extra Virgin Olive Oils & Cheese Tasting

Indulge in the authentic flavors of Tuscany with this exclusive wine, olive oil & balsamic vinegar tasting experience just minutes from the heart of San...

45 minutes Free Cancellation

4.0 (9)

from
$63

Truffle Hunting and Tasting in San Gimignano with a Tuscan Lunch

TOUR HIGHLIGHTS • Join a truffle hunter and his trained dog to go in search of truffles in the wood • Taste eleven local wines, …More

Florence, Italy

5.0 (1)

Truffle Hunting and Tasting in San Gimignano with a Tuscan Lunch

TOUR HIGHLIGHTS • Join a truffle hunter and his trained dog to go in search of truffles in the wood • Taste eleven local wines,...

6 hours Free Cancellation

5.0 (1)

from
$426

Tuscan Food Cooking Class in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Sit down to taste everything you created along with wine tasting from the library vintage reserves • Learn from a passionate local …More

Florence, Italy

5.0 (1)

Tuscan Food Cooking Class in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Sit down to taste everything you created along with wine tasting from the library vintage reserves • Learn from a passionate local...

5 hours Free Cancellation

5.0 (1)

from
$278

HALF-DAY Tour to Chianti Wine Region: CHIANTI COLORS & FLAVORS

TOUR HIGHLIGHTS • Discover the heart of Tuscany, the Chianti wine region, and its rolling hills and olive groves! • Travel with a knowledgeable tour …More

Florence, Italy

4.7 (3)

HALF-DAY Tour to Chianti Wine Region: CHIANTI COLORS & FLAVORS

TOUR HIGHLIGHTS • Discover the heart of Tuscany, the Chianti wine region, and its rolling hills and olive groves! • Travel with a knowledgeable tour...

5 hours 15 minutes Free Cancellation

4.7 (3)

from
$134

Florence Wine Tasting Tour in the City Center! Local Expert!

Discover Florence's rich wine history on this urban wine tour that leads you through the heart of the city. As you stroll through the cities …More

Florence, Italy

5.0 (1)

Florence Wine Tasting Tour in the City Center! Local Expert!

Discover Florence's rich wine history on this urban wine tour that leads you through the heart of the city. As you stroll through the cities...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$97

The Tuscany Countryside from Livorno Port. Lunch and wine in the farm included!

Volterra is a three thousand year-old small town nested on the top of a hill more than 500 m high (1650 feet) on the sea …More

San Gimignano, Italy

5.0 (1)

The Tuscany Countryside from Livorno Port. Lunch and wine in the farm included!

Volterra is a three thousand year-old small town nested on the top of a hill more than 500 m high (1650 feet) on the sea...

9 hours

5.0 (1)

from
$215

Private Wine Tour Tuscany driver English speaking Limo service

This wine tours with a Mercedes-Benz vehicles and an expert professional driver English speaking that will drive you to see the best that you can …More

Florence, Italy

5.0 (1)

Private Wine Tour Tuscany driver English speaking Limo service

This wine tours with a Mercedes-Benz vehicles and an expert professional driver English speaking that will drive you to see the best that you can...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$838

Private Wine Tour 2 top wineries of Chianti Classico Limo Service

A wonderfull day with many stops for panoramic photos of the beautifull countryside of Chianti, guided from an English speacking professional driver with a confortable …More

Florence, Italy

5.0 (1)

Private Wine Tour 2 top wineries of Chianti Classico Limo Service

A wonderfull day with many stops for panoramic photos of the beautifull countryside of Chianti, guided from an English speacking professional driver with a confortable...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$895

Shore Excursion from Livorno to Chianti area with Wine Tasting & Lunch

Private day trip to the famous Chianti area in Southern Tuscany, for a fantastic excursion in a Chianti vineyard. You will appreciate the various types …More

Livorno, Italy

5.0 (1)

Shore Excursion from Livorno to Chianti area with Wine Tasting & Lunch

Private day trip to the famous Chianti area in Southern Tuscany, for a fantastic excursion in a Chianti vineyard. You will appreciate the various types...

9 hours Free Cancellation

5.0 (1)

from
$551

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

Upon your arrival we will welcome you to visit the winery and discover all the winemaking processes together. After the visit we will reach the …More

Montepulciano, Italy

4.3 (8)

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

Upon your arrival we will welcome you to visit the winery and discover all the winemaking processes together. After the visit we will reach the...

4 hours

4.3 (8)

from
$114

Super Tasty Full-day Guided Tour of Florence Food Wine Art Top Sites & Eateries

Enjoy this 5.5-hours full day tour experience in Florence. A one of a kind tour that combines breathtaking views, amazing monuments and a gourmet promenade …More

Florence, Italy

4.7 (3)

Super Tasty Full-day Guided Tour of Florence Food Wine Art Top Sites & Eateries

Enjoy this 5.5-hours full day tour experience in Florence. A one of a kind tour that combines breathtaking views, amazing monuments and a gourmet promenade...

5 hours 30 minutes Free Cancellation

4.7 (3)

from
$217

Private Tour Pisa, countryside with wine tasting

The winetasting is included in the price. Exclusivity: exclusive service in top-of-the-range Mercedes-Benz Business Van. This type of excursion is ONLY present in our catalog …More

Livorno, Italy

5.0 (1)

Private Tour Pisa, countryside with wine tasting

The winetasting is included in the price. Exclusivity: exclusive service in top-of-the-range Mercedes-Benz Business Van. This type of excursion is ONLY present in our catalog...

8 hours Free Cancellation

5.0 (1)

from
$216

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and …More

Chianti, Italy

4.2 (6)

Montalcino wine tour

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and...

9 hours

4.2 (6)

from
$397

Wine Tasting & Dinner with wine expert in the heart of Florence

During this dinner/ tasting sitting comfortably in the tasting room of our "wine lounge" you'll taste five wines, unique, which have made Italy and Tuscany …More

Florence, Italy

5.0 (1)

Wine Tasting & Dinner with wine expert in the heart of Florence

During this dinner/ tasting sitting comfortably in the tasting room of our "wine lounge" you'll taste five wines, unique, which have made Italy and Tuscany...

2 hours

5.0 (1)

from
$126

The Complete Wine Tour Brunello, Nobile, Chianti wine experience

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this 10-hour private excursion from Florence. Enjoy 2 or 3 different regional varieties: …More

Florence, Italy

4.0 (7)

The Complete Wine Tour Brunello, Nobile, Chianti wine experience

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this 10-hour private excursion from Florence. Enjoy 2 or 3 different regional varieties:...

10 hours Free Cancellation

4.0 (7)

from
$272

Private Hike and Wine Experience in the Chianti Classico region

Walking, discovering, and tasting: In the heart of Tuscany, through the lands of the Chianti region, we accompany you on daily excursions combined with original …More

Chianti, Italy

5.0 (1)

Private Hike and Wine Experience in the Chianti Classico region

Walking, discovering, and tasting: In the heart of Tuscany, through the lands of the Chianti region, we accompany you on daily excursions combined with original...

1 day 5 hours Free Cancellation

5.0 (1)

from
$154

Half-Day Chianti Wine and Olive Oil Tour from Viareggio

The best way to enjoy a Chianti Wine tasting in Tuscany. Our small group sizes mean a more intimate and fun Tuscan Wine experience for …More

Versilia, Italy

4.2 (5)

Half-Day Chianti Wine and Olive Oil Tour from Viareggio

The best way to enjoy a Chianti Wine tasting in Tuscany. Our small group sizes mean a more intimate and fun Tuscan Wine experience for...

6 hours Free Cancellation

4.2 (5)

from
$159

Private Wine & Evo oil tasting with Truffle Meal

Treat yourself to a truffle lunch in an authentic Tuscan atmosphere on a family farm. The experience will start with a detailed introduction to the …More

San Gimignano, Italy

4.3 (3)

Private Wine & Evo oil tasting with Truffle Meal

Treat yourself to a truffle lunch in an authentic Tuscan atmosphere on a family farm. The experience will start with a detailed introduction to the...

90 to 120 minutes Free Cancellation

4.3 (3)

from
$98

Wine Tasting & Tuscan Lunch - Food and Drinks included

A break of pleasure! Try your typical Tuscan products prepared by our cook all with genuine and fresh ingredients with Tasting of Wines and Olive …More

Poggibonsi, Italy

4.5 (4)

Wine Tasting & Tuscan Lunch - Food and Drinks included

A break of pleasure! Try your typical Tuscan products prepared by our cook all with genuine and fresh ingredients with Tasting of Wines and Olive...

2 hours Free Cancellation

4.5 (4)

from
$57

Tuscany Highlights and Wine Private Car Tour from Florence

See the world-famous Leaning Tower of Pisa, explore San Gimignano and Siena, and enjoy a wine tasting in Chianti on a full-day road trip from …More

Florence, Italy

5.0 (1)

Tuscany Highlights and Wine Private Car Tour from Florence

See the world-famous Leaning Tower of Pisa, explore San Gimignano and Siena, and enjoy a wine tasting in Chianti on a full-day road trip from...

12 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$352

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?