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 →

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint …More

Siena, Italy

5.0 (2)

Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from SIENA

Go on an artistic, spiritual quest to Assisi and discover the divinity in the air and in Giotto's brushstrokes, which depict the life of Saint...

9 hours Hotel pickup offered

5.0 (2)

from
$227

Val d Orcia Gourmet Food Tour from Siena

A private tour in a small boutique winery with wine tasting. Gourmet food experience in a local home. Enjoy a taste of several local and …More

Siena, Italy

5.0 (2)

Val d Orcia Gourmet Food Tour from Siena

A private tour in a small boutique winery with wine tasting. Gourmet food experience in a local home. Enjoy a taste of several local and...

7 hours Hotel pickup offered

5.0 (2)

from
$98

Full-Day Car Tour Siena San Gimignano and Chianti from Florence

A full-day tour to Siena and to San Gimignano, the medieval town considered a Unesco World Heritage Site. Lunch will be held at the Castle …More

Florence, Italy

5.0 (2)

Full-Day Car Tour Siena San Gimignano and Chianti from Florence

A full-day tour to Siena and to San Gimignano, the medieval town considered a Unesco World Heritage Site. Lunch will be held at the Castle...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$911

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

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

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

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 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

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

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
$1,795

Private Cooking Class in Tuscany | Hand Made Pasta

You will be welcomed into our country house, immersed in the beauty of the rolling Sienese hills. I am a professional Chef and Sommelier, and …More

Arezzo, Italy

5.0 (1)

Private Cooking Class in Tuscany | Hand Made Pasta

You will be welcomed into our country house, immersed in the beauty of the rolling Sienese hills. I am a professional Chef and Sommelier, and...

4 hours 30 minutes Free Cancellation

5.0 (1)

from
$212

Florence Exclusive VIP Wine Tasting Tour with a Special VIP Gift

This exclusive experience invites you to discover the rich winemaking tradition of Tuscany through a personalized tasting. Guided by an expert sommelier, you’ll have the …More

Florence, Italy

5.0 (1)

Florence Exclusive VIP Wine Tasting Tour with a Special VIP Gift

This exclusive experience invites you to discover the rich winemaking tradition of Tuscany through a personalized tasting. Guided by an expert sommelier, you’ll have the...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$132

Around Tuscany: Carrara Marbles, Pisa & Lucca

Explore the white marble quarries of Carrara, famous for its beauty and used in many works of art, including those by Michelangelo. You will have …More

Florence, Italy

5.0 (1)

Around Tuscany: Carrara Marbles, Pisa & Lucca

Explore the white marble quarries of Carrara, famous for its beauty and used in many works of art, including those by Michelangelo. You will have...

11 hours Free Cancellation

5.0 (1)

from
$205

Retrospettiva di Marchesale Wine Tasting and Tour in Bolgheri

Let us take you on a journey through time through the vintages of Marchesale, our Bolgheri Superiore DOC. Each bottle holds a fascinating story, a …More

Livorno, Italy

5.0 (1)

Retrospettiva di Marchesale Wine Tasting and Tour in Bolgheri

Let us take you on a journey through time through the vintages of Marchesale, our Bolgheri Superiore DOC. Each bottle holds a fascinating story, a...

1 hour 15 minutes Free Cancellation

5.0 (1)

from
$91

Horseback Ridings and Wine Tastings in a Winery of San Gimignano

Explore San Gimignano on horseback! Ride through vineyards & olive groves, taking in breathtaking Tuscan scenery. Discover scenic trails & enjoy a delicious regional appetizer …More

Florence, Italy

5.0 (1)

Horseback Ridings and Wine Tastings in a Winery of San Gimignano

Explore San Gimignano on horseback! Ride through vineyards & olive groves, taking in breathtaking Tuscan scenery. Discover scenic trails & enjoy a delicious regional appetizer...

5 hours Free Cancellation

5.0 (1)

from
$405

FLORENCE FOOD TOUR:Markets,street food & Florentine T-bone steak!

Unsure how to spend your time? Food or Art? Why not both? This 3,5 hours walking tour is a delicious way to explore the city …More

Florence, Italy

5.0 (1)

FLORENCE FOOD TOUR:Markets,street food & Florentine T-bone steak!

Unsure how to spend your time? Food or Art? Why not both? This 3,5 hours walking tour is a delicious way to explore the city...

3 hours 30 minutes Free Cancellation

5.0 (1)

from
$156

From Livorno Port: Private Siena & San Gimignano with Wine Lunch

A private full-day shore excursion from Livorno Port to Siena and San Gimignano, with a farm lunch and wine tasting. • Your driver meets you …More

Livorno, Italy

5.0 (1)

From Livorno Port: Private Siena & San Gimignano with Wine Lunch

A private full-day shore excursion from Livorno Port to Siena and San Gimignano, with a farm lunch and wine tasting. • Your driver meets you...

9 hours Free Cancellation

5.0 (1)

from
$188

From Florence: Private San Gimignano & Chianti Tour with Lunch

A private day from Florence through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or apartment in …More

Florence, Italy

5.0 (1)

From Florence: Private San Gimignano & Chianti Tour with Lunch

A private day from Florence through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or apartment in...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$240

Wine Tour & Tasting - Organic Chianti & Supertuscan

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. - …More

Siena, Italy

5.0 (1)

Wine Tour & Tasting - Organic Chianti & Supertuscan

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. -...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$51

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:

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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?