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 →

Florence Luxury Wine Tasting Experience and cold cuts & sommelier

Luxury experience conducted by an expert Italian Sommelier will guide you on a journey through the different nuances of a wine tasting with Tuscan wineries. …More

Florence, Italy

5.0 (2)

Florence Luxury Wine Tasting Experience and cold cuts & sommelier

Luxury experience conducted by an expert Italian Sommelier will guide you on a journey through the different nuances of a wine tasting with Tuscan wineries....

1 hour Free Cancellation

5.0 (2)

from
$73

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4 …More

Arezzo, Italy

4.7 (9)

Lunch Time Tasting & Winery Tour

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4...

2 hours Free Cancellation

4.7 (9)

from
$69

Painting and Wine Tasting in the Heart of the Tuscan Countryside

With Tara & Branton you will receive a warm welcome and their complete attention due to small groups only. With the freedom to release your …More

5.0 (2)

Painting and Wine Tasting in the Heart of the Tuscan Countryside

With Tara & Branton you will receive a warm welcome and their complete attention due to small groups only. With the freedom to release your...

4 hours Free Cancellation

5.0 (2)

from
$200

Small Group Vespa Tour: Medieval Villages, Lunch and Wine Tasting

Ride the original Vespa, the iconic Italian scooter through the scenic hill sides of Tuscany, an immersion into the Italian “Dolce Vita”. No Experience Required. …More

Florence, Italy

5.0 (2)

Small Group Vespa Tour: Medieval Villages, Lunch and Wine Tasting

Ride the original Vespa, the iconic Italian scooter through the scenic hill sides of Tuscany, an immersion into the Italian “Dolce Vita”. No Experience Required....

7 to 8 hours Free Cancellation

5.0 (2)

from
$228

Private tasting of wines and oil to discover Lucca Ducale

Our tasting tours are a journey to discover the history of Lucca and the taste given by organic production that pays attention to the territory. …More

Lucca, Italy

5.0 (2)

Private tasting of wines and oil to discover Lucca Ducale

Our tasting tours are a journey to discover the history of Lucca and the taste given by organic production that pays attention to the territory....

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$46

Today we will spend a day in one of the most famous Wine Regions in the World, the Bolgheri DOC where excellent wines are produced. …More

Livorno, Italy

5.0 (3)

Bolgheri Wineries and Tuscany Tour

Today we will spend a day in one of the most famous Wine Regions in the World, the Bolgheri DOC where excellent wines are produced....

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,118

Quad excursion in the woods with visit to the cellar and tasting

Come and try an authentic Maremma experience! Quad excursions to discover the "Bandite di Scarlino" woods with visit to the cellar and wine tasting. Suggestive …More

4.8 (4)

Quad excursion in the woods with visit to the cellar and tasting

Come and try an authentic Maremma experience! Quad excursions to discover the "Bandite di Scarlino" woods with visit to the cellar and wine tasting. Suggestive...

2 hours 30 minutes Free Cancellation

4.8 (4)

from
$103

Visit Of The Chianti Classico And The Tuscan Countryside

You will have an unique experience with speaking English driver, you will feel the real atmosphere of Tuscany in the beauty of the Nature and …More

Florence, Italy

5.0 (4)

Visit Of The Chianti Classico And The Tuscan Countryside

You will have an unique experience with speaking English driver, you will feel the real atmosphere of Tuscany in the beauty of the Nature and...

8 hours Free Cancellation

5.0 (4)

from
$253

Montecatini Private Day Trip To Chianti & San Gimignano

A customized day trip of Chianti countryside and San Gimignano for the discerning traveler seeking an authentic Italian experience on a small group tour for …More

Montecatini Terme, Italy

5.0 (2)

Montecatini Private Day Trip To Chianti & San Gimignano

A customized day trip of Chianti countryside and San Gimignano for the discerning traveler seeking an authentic Italian experience on a small group tour for...

9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$1,022

Private Tour from Livorno - Florence with Wine Tasting

Experience the best of Tuscany on this exclusive shore excursion from Livorno. Discover the beauty of Florence, enjoy free time to explore the city, and …More

Livorno, Italy

5.0 (3)

Private Tour from Livorno - Florence with Wine Tasting

Experience the best of Tuscany on this exclusive shore excursion from Livorno. Discover the beauty of Florence, enjoy free time to explore the city, and...

8 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$170

Private Florence Evening Food Tour: Oil, Wine, Old-school dishes

Reserve a private experience just for you and your travel mates. You will delight your palate with Tuscan delicacies, fine wine and old-school dishes. Your …More

Florence, Italy

5.0 (2)

Private Florence Evening Food Tour: Oil, Wine, Old-school dishes

Reserve a private experience just for you and your travel mates. You will delight your palate with Tuscan delicacies, fine wine and old-school dishes. Your...

3 hours Free Cancellation

5.0 (2)

from
$307

The selections - visit with Bolgheri wine tasting

Live an authentic experience in the heart of Bolgheri with our guided tour of the Estate. We will accompany you on a walk through our …More

Livorno, Italy

4.6 (5)

The selections - visit with Bolgheri wine tasting

Live an authentic experience in the heart of Bolgheri with our guided tour of the Estate. We will accompany you on a walk through our...

2 hours Free Cancellation

4.6 (5)

from
$52

Private Photo Shooting on Horseback and at Wine Estate's

A professional photo-shooting on horseback and while tasting the best Chianti wines in a scenic location will give the guests an unbeatable chance to escape …More

Florence, Italy

5.0 (1)

Private Photo Shooting on Horseback and at Wine Estate's

A professional photo-shooting on horseback and while tasting the best Chianti wines in a scenic location will give the guests an unbeatable chance to escape...

6 hours 30 minutes Free Cancellation

5.0 (1)

from
$556

- A wine expert who will guide you through the tasting journey. - Wine tasting that includes 2 Spumante and 2 Red Wines, and 5 …More

Siena, Italy

5.0 (1)

Tuscan Wine Tasting and Local Cheeses

- A wine expert who will guide you through the tasting journey. - Wine tasting that includes 2 Spumante and 2 Red Wines, and 5...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$41

In the Heart of Chianti Classico : Wine, Winery and Tradition

Discover Chianti Classico with a visit and tasting in Viticcio: explore the winery, discover the winemaking and taste our best wines. An authentic Chianti experience! …More

Chianti, Italy

5.0 (2)

In the Heart of Chianti Classico : Wine, Winery and Tradition

Discover Chianti Classico with a visit and tasting in Viticcio: explore the winery, discover the winemaking and taste our best wines. An authentic Chianti experience!...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$39

Wine and Dine in Chianti Classico Exclusive Private Dinner

Step into the warm, intimate setting of the private wine cellar for an unforgettable dining experience. Savor a handcrafted 4-course meal, prepared exclusively for you …More

Florence, Italy

5.0 (1)

Wine and Dine in Chianti Classico Exclusive Private Dinner

Step into the warm, intimate setting of the private wine cellar for an unforgettable dining experience. Savor a handcrafted 4-course meal, prepared exclusively for you...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$284

Pisa Tour and Wine Tasting on the Pisan Hills

Our transport option stands out for the rare occasion to visit unique yet undiscovered places - the scenic vineyards of the Pisa hills, the secrets …More

Livorno, Italy

5.0 (2)

Pisa Tour and Wine Tasting on the Pisan Hills

Our transport option stands out for the rare occasion to visit unique yet undiscovered places - the scenic vineyards of the Pisa hills, the secrets...

2 to 8 hours Free Cancellation

5.0 (2)

from
$742

Tuscany Private Guided Wine Tasting Tour by Car

Explore the picturesque landscapes of Tuscany on a captivating day trip from Florence. This intimate journey invites you to savor the rich flavors of Brunello …More

Livorno, Italy

5.0 (2)

Tuscany Private Guided Wine Tasting Tour by Car

Explore the picturesque landscapes of Tuscany on a captivating day trip from Florence. This intimate journey invites you to savor the rich flavors of Brunello...

10 hours Free Cancellation

5.0 (2)

from
$1,825

THE MASTER of Chianti Classico 3 Top Wineries Limousine Service

A wonderful day with many stops for panoramic photos on the beautiful countryside of Chianti classico, the famous countryside of Tuscany, guided from an English …More

Florence, Italy

5.0 (1)

THE MASTER of Chianti Classico 3 Top Wineries Limousine Service

A wonderful day with many stops for panoramic photos on the beautiful countryside of Chianti classico, the famous countryside of Tuscany, guided from an English...

9 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,255

A scenic ride along the Via Francigena to San Gimignano: the home of Vernaccia wine and world-renowned gelato. With our E-bikes you’ll make your way …More

Florence, Italy

5.0 (1)

Chianti to San Gimignano E-bike Tour

A scenic ride along the Via Francigena to San Gimignano: the home of Vernaccia wine and world-renowned gelato. With our E-bikes you’ll make your way...

8 hours Free Cancellation

5.0 (1)

from
$357

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?