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 →

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving …More

Siena, Italy

5.0 (20)

Private Off Road Wine Tour in Chianti

Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving...

6 hours Free Cancellation

5.0 (20)

from
$311

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti …More

Siena, Italy

5.0 (20)

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti...

3 hours Free Cancellation

5.0 (20)

from
$86

Fresh Pasta Class in Florence with unlimited Wine

Step into history as you join our class held in one of the oldest restaurants in Florence, nestled within a stunning building that dates back …More

Florence, Italy

4.9 (20)

Fresh Pasta Class in Florence with unlimited Wine

Step into history as you join our class held in one of the oldest restaurants in Florence, nestled within a stunning building that dates back...

3 hours 15 minutes Free Cancellation

4.9 (20)

from
$67

Private Tour to Siena and San Gimignano with Wine Tasting & Lunch

Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover …More

Florence, Italy

4.8 (20)

Private Tour to Siena and San Gimignano with Wine Tasting & Lunch

Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover...

8 hours Hotel pickup offered Free Cancellation

4.8 (20)

from
$563

Chianti Vineyards Tours in Private Luxury Van from Florence

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent …More

Florence, Italy

5.0 (20)

Chianti Vineyards Tours in Private Luxury Van from Florence

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent...

8 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$815

Half Day Chianti Wine Tour with Private Luxury Van

• Experience for your private group. Visit some of the most famous vineyards, see their wine cellars and taste excellent wines on this 5-hour tour. …More

Florence, Italy

5.0 (20)

Half Day Chianti Wine Tour with Private Luxury Van

• Experience for your private group. Visit some of the most famous vineyards, see their wine cellars and taste excellent wines on this 5-hour tour....

5 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$677

Small family-run winery, certified organic, which produces exclusively from its own grapes with a strong focus on sustainability. We will offer you a private tasting …More

Florence, Italy

5.0 (20)

Classic Wine Tasting by Carus Wines

Small family-run winery, certified organic, which produces exclusively from its own grapes with a strong focus on sustainability. We will offer you a private tasting...

2 hours Free Cancellation

5.0 (20)

from
$23

You will be welcome by the owners of the old tradition family-run business. The Wine&EVO Oil tour will start from the visit of one of …More

Arezzo, Italy

5.0 (19)

Wine & Oil Tasting Experience

You will be welcome by the owners of the old tradition family-run business. The Wine&EVO Oil tour will start from the visit of one of...

1 to 3 hours Free Cancellation

5.0 (19)

from
$45

Private Day Trip Brunello Wine with Lunch from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Wine lovers, dedicate a day to the legendary Brunello! Embark on an extraordinary 9-hour guided tour from Florence. …More

Florence, Italy

5.0 (19)

Private Day Trip Brunello Wine with Lunch from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Wine lovers, dedicate a day to the legendary Brunello! Embark on an extraordinary 9-hour guided tour from Florence....

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (19)

from
$154

Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence

With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even …More

Florence, Italy

5.0 (19)

Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence

With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even...

11 hours Hotel pickup offered Free Cancellation

5.0 (19)

from
$663

From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch

What a better gift for your lover or best friend than visit Tuscany on board of a convertible Tuk Tuk for 2 to explore the …More

San Gimignano, Italy

4.8 (19)

From San Gimignano: Tuscany Wine tour by Tuk Tuk with Lunch

What a better gift for your lover or best friend than visit Tuscany on board of a convertible Tuk Tuk for 2 to explore the...

4 hours Free Cancellation

4.8 (19)

from
$170

Are you passionate about food and wine? Then this is the perfect tour for you! If you're looking for an authentic gastronomic experience in Florence, …More

Florence, Italy

5.0 (19)

Food Tour Florence Small Groups

Are you passionate about food and wine? Then this is the perfect tour for you! If you're looking for an authentic gastronomic experience in Florence,...

2 hours 30 minutes Free Cancellation

5.0 (19)

from
$97

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and …More

Siena, Italy

5.0 (19)

Exclusive Wine Tour and Tasting Experience in Siena

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and...

3 hours 30 minutes Free Cancellation

5.0 (19)

from
$171

Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

San Gimignano, Italy

4.8 (19)

Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes Free Cancellation

4.8 (19)

from
$78

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines …More

Siena, Italy

5.0 (19)

Chianti Classico E-Bike Tour

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines...

5 to 6 hours Free Cancellation

5.0 (19)

from
$240

Private Cinque Terre by Ferry with stop in Pisa from Florence

Discover the beauty of the Italian Riviera on our Cinque Terre by Ferry with Stop in Pisa from Florence! Visit two picturesque fishing villages on …More

Florence, Italy

5.0 (18)

Private Cinque Terre by Ferry with stop in Pisa from Florence

Discover the beauty of the Italian Riviera on our Cinque Terre by Ferry with Stop in Pisa from Florence! Visit two picturesque fishing villages on...

12 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$665

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This …More

Florence, Italy

5.0 (18)

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This...

10 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$330

Private Off Road Wine Tour in Chianti from Florence

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a Land Rover Defender. There’s a special magic in exploring the hidden gravel …More

Florence, Italy

5.0 (18)

Private Off Road Wine Tour in Chianti from Florence

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a Land Rover Defender. There’s a special magic in exploring the hidden gravel...

7 hours Hotel pickup offered Free Cancellation

5.0 (18)

from
$338

Private Wine & Evo Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

San Gimignano, Italy

4.9 (18)

Private Wine & Evo Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes Free Cancellation

4.9 (18)

from
$78

Book a tasting of our organic/biodynamic wines produced on the Lucca hills; we will take a tour of the vineyard near the cellar, a visit …More

Versilia, Italy

5.0 (18)

Lucca - Wine tasting at Tenuta Mareli

Book a tasting of our organic/biodynamic wines produced on the Lucca hills; we will take a tour of the vineyard near the cellar, a visit...

1 hour 30 minutes Free Cancellation

5.0 (18)

from
$34

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?