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 →

Garden Tour and Authentic Italian Pasta Making Class in Tuscany

This Tuscany cooking class is ideal for anyone looking to dive into Italian culture, learn new cooking skills, and spend time with welcoming locals in …More

5.0 (3)

Garden Tour and Authentic Italian Pasta Making Class in Tuscany

This Tuscany cooking class is ideal for anyone looking to dive into Italian culture, learn new cooking skills, and spend time with welcoming locals in...

3 hours Free Cancellation

5.0 (3)

from
$135

Private Val d'Orcia Experience - A cinematic universe

Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting Val d’Orcia, a Unesco World Heritage Site. The …More

Florence, Italy

5.0 (3)

Private Val d'Orcia Experience - A cinematic universe

Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting Val d’Orcia, a Unesco World Heritage Site. The...

12 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$657

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors …More

Siena, Italy

5.0 (4)

Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors...

6 hours Free Cancellation

5.0 (4)

from
$274

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a …More

Arezzo, Italy

4.6 (7)

Private tour Wine and cheese a perfect combinations val 'Orcia

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a...

8 to 9 hours Hotel pickup offered Free Cancellation

4.6 (7)

from
$320

Florence Afternoon Food & Wine Tasting with Walking Tour

Savor the flavors of authentic Tuscan cuisine with this private gourmet food tour in Florence. Visit markets, taste wine, and learn about the region's culinary …More

Florence, Italy

4.6 (7)

Florence Afternoon Food & Wine Tasting with Walking Tour

Savor the flavors of authentic Tuscan cuisine with this private gourmet food tour in Florence. Visit markets, taste wine, and learn about the region's culinary...

3 hours Hotel pickup offered Free Cancellation

4.6 (7)

from
$161

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
$406

Florentine Steak with Wines in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Taste some of the library reserve vintage wines including other wine from the current release vintage • Eat the Fiorentina Steak paired …More

Florence, Italy

5.0 (2)

Florentine Steak with Wines in San Gimignano Winery from Florence

TOUR HIGHLIGHTS • Taste some of the library reserve vintage wines including other wine from the current release vintage • Eat the Fiorentina Steak paired...

4 hours Free Cancellation

5.0 (2)

from
$295

Horseback Riding and Winery Lunch Experience in San Gimignano

TOUR HIGHLIGHTS • Explore San Gimignano, vineyards and olive groves on a horseback ride • Take in the fascinating and warm landscape of the San …More

Florence, Italy

5.0 (2)

Horseback Riding and Winery Lunch Experience in San Gimignano

TOUR HIGHLIGHTS • Explore San Gimignano, vineyards and olive groves on a horseback ride • Take in the fascinating and warm landscape of the San...

4 hours 30 minutes Free Cancellation

5.0 (2)

from
$522

Florence: San Lorenzo Farmers Market Food Tour with Wine Tasting in 4 hours

An English-speaking guide will accompany us in this culinary adventure; we will start from the Central Market to try traditional recipes and meet food artisans. …More

Florence, Italy

5.0 (2)

Florence: San Lorenzo Farmers Market Food Tour with Wine Tasting in 4 hours

An English-speaking guide will accompany us in this culinary adventure; we will start from the Central Market to try traditional recipes and meet food artisans....

4 hours Free Cancellation

5.0 (2)

from
$102

Montepulciano and Chianti in 1 day + lunch&transfer from Florence

Discover Montepulciano and Chianti areas by tasting various vintages and have lunch with a breathtaking view with transfer from Florence. You will visit a historic …More

Florence, Italy

5.0 (2)

Montepulciano and Chianti in 1 day + lunch&transfer from Florence

Discover Montepulciano and Chianti areas by tasting various vintages and have lunch with a breathtaking view with transfer from Florence. You will visit a historic...

11 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$321

Wine tasting and guided tour of the cellar

Fattoria Sorbaiano, a historic farm with a wine and oil production vocation, is located in Montecatini val di Cecina, in the DOC Montescudaio. We organize …More

5.0 (2)

Wine tasting and guided tour of the cellar

Fattoria Sorbaiano, a historic farm with a wine and oil production vocation, is located in Montecatini val di Cecina, in the DOC Montescudaio. We organize...

1 hour Free Cancellation

5.0 (2)

from
$28

Let’s explore the so-called Colline Lucchesi and Montecarlo wine areas. This area is known not only for typical Tuscan Sangiovese and Trebbiano grapes, but also …More

Versilia, Italy

5.0 (2)

Wine tour and lunch in Lucca area

Let’s explore the so-called Colline Lucchesi and Montecarlo wine areas. This area is known not only for typical Tuscan Sangiovese and Trebbiano grapes, but also...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$402

Private driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show …More

Florence, Italy

5.0 (2)

Private driver for Florence city sightseeing & Wine Tour Chianti

Hi I'm Gianluca, I was born in Florence and I have a long experience on Tours, I know my places and I love to show...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$930

Private Pisa & Tuscany Wine Tour with Tasting & Lunch

Experience the best of Tuscany on this private shore excursion from Livorno, combining the world-famous Leaning Tower of Pisa with an authentic Tuscany wine tour. …More

Livorno, Italy

5.0 (4)

Private Pisa & Tuscany Wine Tour with Tasting & Lunch

Experience the best of Tuscany on this private shore excursion from Livorno, combining the world-famous Leaning Tower of Pisa with an authentic Tuscany wine tour....

8 hours Free Cancellation

5.0 (4)

from
$226

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

Siena, Italy

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$272

Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its …More

Florence, Italy

5.0 (4)

Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

“If you truly want to experience the Chianti region, this is the tour you’ve been looking for!” The Chianti region is celebrated worldwide for its...

6 to 7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$281

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes …More

Florence, Italy

5.0 (3)

Ferrari Parmesan Cheese Balsamic Vinegar wine & food PRIVATE TOUR from FLORENCE

Private, Exclusive, Customizable, door-to-door tour of Modena area: * Parmesan cheese tasting * Ferrari museum * Balsamic vinegar tasting * Lambrusco tasting * Luxury Mercedes...

10 hours Hotel pickup offered

5.0 (3)

from
$276

Private E-bike Tour in Chianti from Florence

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills …More

Florence, Italy

5.0 (4)

Private E-bike Tour in Chianti from Florence

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills...

7 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$303

Private E-bike Tour in Chianti from San Gimignano

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills …More

San Gimignano, Italy

4.7 (3)

Private E-bike Tour in Chianti from San Gimignano

Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills...

6 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$299

Make your bland bottle and cork Your wine in center of Florence

This is the only wine workshop in Florence where you can create your personal blend. A small group that allows you to be pampered with …More

Florence, Italy

5.0 (3)

Make your bland bottle and cork Your wine in center of Florence

This is the only wine workshop in Florence where you can create your personal blend. A small group that allows you to be pampered with...

1 hour 45 minutes

5.0 (3)

from
$148

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?