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 Tasting at Your Villa in Umbria & Tuscany

Imagine spending a relaxing evening with friends or family, surrounded by the beautiful landscapes of Umbria or Tuscany, while a professional local sommelier comes directly …More

Arezzo, Italy

5.0 (17)

Private Wine Tasting at Your Villa in Umbria & Tuscany

Imagine spending a relaxing evening with friends or family, surrounded by the beautiful landscapes of Umbria or Tuscany, while a professional local sommelier comes directly...

2 hours Free Cancellation

5.0 (17)

from
$46

Wine Tour Experience at Agricola Tamburini

To experience the top of tuscany!!! drinking real taste wines and enjoyng the authenthic atmosphere of a family business!!! …More

Livorno, Italy

5.0 (12)

Wine Tour Experience at Agricola Tamburini

To experience the top of tuscany!!! drinking real taste wines and enjoyng the authenthic atmosphere of a family business!!!...

1 to 30 minutes Free Cancellation

5.0 (12)

from
$63

Private tour from Livorno port to Chianti Wine Region

This private tour will make you discover and enjoy the essence of this land known for its breathtaking landscapes that for centuries has been giving …More

Livorno, Italy

5.0 (5)

Private tour from Livorno port to Chianti Wine Region

This private tour will make you discover and enjoy the essence of this land known for its breathtaking landscapes that for centuries has been giving...

9 hours Free Cancellation

5.0 (5)

from
$250

Chianti Wine Tasting Tour from Florence (2 Wineries)

WINE LOVERS, ARE YOU READY? This is a must do day trip for Wine Lovers! We will pick you up directly by your accommodation in …More

Florence, Italy

5.0 (13)

Chianti Wine Tasting Tour from Florence (2 Wineries)

WINE LOVERS, ARE YOU READY? This is a must do day trip for Wine Lovers! We will pick you up directly by your accommodation in...

8 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$1,118

Florence and Wine Tasting Private Tour from Livorno

ARE YOU READY FOR A GREAT DAY with LIMOSERVICEINITALY? FLORENCE AND WINE TASTING IN TUSCANY Enjoy a day exploring the highlights of Florence and a …More

Livorno, Italy

5.0 (13)

Florence and Wine Tasting Private Tour from Livorno

ARE YOU READY FOR A GREAT DAY with LIMOSERVICEINITALY? FLORENCE AND WINE TASTING IN TUSCANY Enjoy a day exploring the highlights of Florence and a...

9 hours Hotel pickup offered Free Cancellation

5.0 (13)

from
$1,004

This full day tour is perfect for first time visitors or anyone interested in combining sightseeing and a complete wine & food experience in Tuscany …More

Florence, Italy

5.0 (10)

Tuscany off the beaten paths

This full day tour is perfect for first time visitors or anyone interested in combining sightseeing and a complete wine & food experience in Tuscany...

8 hours Free Cancellation

5.0 (10)

from
$217

Emanuele, a licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best …More

Siena, Italy

5.0 (17)

Discover Chianti Classico Wines

Emanuele, a licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best...

8 hours

5.0 (17)

from
$281

Siena and Chianti Wineries Excursion by Private Luxury Van from Florence

• Experience for your private group. • Explore the art, culture and medieval history of Italy in this private 8-hour Siena and Chianti countryside tour …More

Florence, Italy

4.9 (12)

Siena and Chianti Wineries Excursion by Private Luxury Van from Florence

• Experience for your private group. • Explore the art, culture and medieval history of Italy in this private 8-hour Siena and Chianti countryside tour...

8 hours Hotel pickup offered

4.9 (12)

from
$804

4 Wines Tasting with 2 Tuscan Cheeses & Tour at the winery

We have a large wine-tasting room dedicated, where the guests can sit at tables. They will taste 4 wines (2 IGT Toscana Wines, 1 Chianti …More

Florence, Italy

5.0 (14)

4 Wines Tasting with 2 Tuscan Cheeses & Tour at the winery

We have a large wine-tasting room dedicated, where the guests can sit at tables. They will taste 4 wines (2 IGT Toscana Wines, 1 Chianti...

1 hour 40 minutes

5.0 (14)

from
$42

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally …More

Siena, Italy

4.9 (11)

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally...

4 hours Free Cancellation

4.9 (11)

from
$251

Private Tour: Chianti Winery, Montefioralle, and Greve in Chianti

Enjoy a taste of Tuscany on a 5-hour morning or afternoon escorted tour to the Chianti region from Florence. With a guide just for your sole …More

Florence, Italy

4.5 (24)

Private Tour: Chianti Winery, Montefioralle, and Greve in Chianti

Enjoy a taste of Tuscany on a 5-hour morning or afternoon escorted tour to the Chianti region from Florence. With a guide just for your sole...

5 hours Free Cancellation

4.5 (24)

from
$138

Chianti & Supertuscan Tour 2 Wineries Small Group 8 people max from Florence

Live as a Tuscan is out way to say. Don't loose the oportunity to visit places where Tuscan are usually to spend time. If you …More

Florence, Italy

5.0 (5)

Chianti & Supertuscan Tour 2 Wineries Small Group 8 people max from Florence

Live as a Tuscan is out way to say. Don't loose the oportunity to visit places where Tuscan are usually to spend time. If you...

6 hours Free Cancellation

5.0 (5)

from
$158

Private Tuscany Day Trip from Florence Including the Leaning Tower of Pisa

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 (8)

Private Tuscany Day Trip from Florence Including the Leaning Tower of Pisa

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 (8)

from
$1,095

Private tasting of organic wines in the cellar in Arezzo

Our cellar has a century of history, it is located in the urban fabric a short distance from the center of Arezzo, reachable by car …More

Arezzo, Italy

5.0 (14)

Private tasting of organic wines in the cellar in Arezzo

Our cellar has a century of history, it is located in the urban fabric a short distance from the center of Arezzo, reachable by car...

1 hour 30 minutes Free Cancellation

5.0 (14)

from
$29

Discovering the Bolgheri vineyards and tasting local products

Immerse yourself in our exclusive location to taste excellent wines that convey all the passion we have. There will be a trained person who will …More

Livorno, Italy

4.8 (15)

Discovering the Bolgheri vineyards and tasting local products

Immerse yourself in our exclusive location to taste excellent wines that convey all the passion we have. There will be a trained person who will...

1 hour 30 minutes Free Cancellation

4.8 (15)

from
$32

Original Private Tuscany tour by Vintage Beetle car & Wine

Explore Tuscany in style with a classic vintage Beetle car tour from 1977. Enjoy breathtaking views, visit two renowned wineries, and taste exceptional wines including …More

4.9 (9)

Original Private Tuscany tour by Vintage Beetle car & Wine

Explore Tuscany in style with a classic vintage Beetle car tour from 1977. Enjoy breathtaking views, visit two renowned wineries, and taste exceptional wines including...

5 hours

4.9 (9)

from
$272

Montecarlo (Lucca) and Wine Tasting from Lucca Private Tour

Your tour will start by visiting a Local Winery on the countryside. After a walk around the vineyards and olive trees we will visit the …More

Lucca, Italy

4.8 (5)

Montecarlo (Lucca) and Wine Tasting from Lucca Private Tour

Your tour will start by visiting a Local Winery on the countryside. After a walk around the vineyards and olive trees we will visit the...

4 to 5 hours Free Cancellation

4.8 (5)

from
$158

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
$318

Chianti Lovers Two Wineries Tour With Lunch from Florence

Travel through the Chianti Classico hills, located in the heart of Tuscany’s Chianti wine district and lunch with tipical products. This day trip from Florence …More

Florence, Italy

5.0 (2)

Chianti Lovers Two Wineries Tour With Lunch from Florence

Travel through the Chianti Classico hills, located in the heart of Tuscany’s Chianti wine district and lunch with tipical products. This day trip from Florence...

7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$221

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
$261

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?