Top Tuscany Wine Tasting & Winery Tours

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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 →

Menu with a “View” in the enchantment of the Tuscan hills

Our farmhouse is the perfect location to enjoy, together with the typical Tuscan cuisine, the undisputed charm of the breathtaking panorama that lies on the …More

Montepulciano, Italy

4.5 (13)

Menu with a “View” in the enchantment of the Tuscan hills

Our farmhouse is the perfect location to enjoy, together with the typical Tuscan cuisine, the undisputed charm of the breathtaking panorama that lies on the...

3 hours Free Cancellation

4.5 (13)

from
$98

Experience the pure bliss of this amazing experience in one of the most exclusive natural spring water locations, the springs at San Filippo. The calciferous …More

Florence, Italy

5.0 (5)

Tuscany Natural Spring Tour

Experience the pure bliss of this amazing experience in one of the most exclusive natural spring water locations, the springs at San Filippo. The calciferous...

9 hours

5.0 (5)

from
$427

Private Pisa & Lucca Day Experience from Florence

Explore the heart of beautiful Tuscany visiting two of Italy’s most cherished towns—Pisa and Lucca. One town is renowned for its medieval walls and stunning …More

Florence, Italy

5.0 (8)

Private Pisa & Lucca Day Experience from Florence

Explore the heart of beautiful Tuscany visiting two of Italy’s most cherished towns—Pisa and Lucca. One town is renowned for its medieval walls and stunning...

9 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$794

Tasting of the Best Wines in Siena in an Etruscan Crypt

Taste the best Tuscan and national wines, accompanied by a selection of tasty local pecorino cheeses in a suggestive Etruscan crypt. My wine shop is …More

Siena, Italy

5.0 (8)

Tasting of the Best Wines in Siena in an Etruscan Crypt

Taste the best Tuscan and national wines, accompanied by a selection of tasty local pecorino cheeses in a suggestive Etruscan crypt. My wine shop is...

1 hour Free Cancellation

5.0 (8)

from
$143

La Maliosa Summer Farm Experience & Wine Tasting

The experience takes place outdoors under our large pergola, where we will guide you through the philosophy of Fattoria La Maliosa, the historic local grape …More

4.7 (15)

La Maliosa Summer Farm Experience & Wine Tasting

The experience takes place outdoors under our large pergola, where we will guide you through the philosophy of Fattoria La Maliosa, the historic local grape...

1 hour 30 minutes

4.7 (15)

from
$51

Florence Uncorked Wine Tasting Experience

This experience is unique because it combines an immersive exploration of Tuscan wine with a deep dive into its historical context. Guests not only taste …More

Florence, Italy

5.0 (2)

Florence Uncorked Wine Tasting Experience

This experience is unique because it combines an immersive exploration of Tuscan wine with a deep dive into its historical context. Guests not only taste...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$57

We will have a tasting of the main labels of the Castello di Bossi, one of the Italian excellence in wine production. What will we …More

Siena, Italy

5.0 (5)

Complete tasting of Castello di Bossi

We will have a tasting of the main labels of the Castello di Bossi, one of the Italian excellence in wine production. What will we...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$103

✅ Authentic Truffle Hunting – Join an expert truffle hunter and trained dogs in a real Tuscan forest. ✅ Hands-On Truffle Cooking Class – Learn …More

San Gimignano, Italy

4.5 (14)

Truffle Hunting and Cooking Class

✅ Authentic Truffle Hunting – Join an expert truffle hunter and trained dogs in a real Tuscan forest. ✅ Hands-On Truffle Cooking Class – Learn...

4 hours 30 minutes Free Cancellation

4.5 (14)

from
$350

Private Tuscany & San Gimignano by Exclusive Vintage Fiat 500

Experience a unique day tour through the Tuscan hills in a vintage Fiat 500. What sets this apart? We cruise fo real through the heart …More

Florence, Italy

5.0 (8)

Private Tuscany & San Gimignano by Exclusive Vintage Fiat 500

Experience a unique day tour through the Tuscan hills in a vintage Fiat 500. What sets this apart? We cruise fo real through the heart...

7 hours Free Cancellation

5.0 (8)

from
$216

1-Hour Experience with Brunello. Visit to the Vineyard and Cellar

The cellarmen of Casato Prime Donne are all women, including the winemaker, a unique feature in Italy that makes this winery a flag for pink …More

Chianti, Italy

5.0 (5)

1-Hour Experience with Brunello. Visit to the Vineyard and Cellar

The cellarmen of Casato Prime Donne are all women, including the winemaker, a unique feature in Italy that makes this winery a flag for pink...

1 hour Free Cancellation

5.0 (5)

from
$40

Super Tuscan & IGT wines, Evo Oil & Balsamic Vinegar Tasting

If you love wine or simply want to learn more, this exclusive Super Tuscan tasting offers a deep dive into one of Tuscany’s most renowned …More

San Gimignano, Italy

4.8 (6)

Super Tuscan & IGT wines, Evo Oil & Balsamic Vinegar Tasting

If you love wine or simply want to learn more, this exclusive Super Tuscan tasting offers a deep dive into one of Tuscany’s most renowned...

1 hour Free Cancellation

4.8 (6)

from
$80

Private Tour Siena San Gimignano and Chianti from Cortona

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore …More

Arezzo, Italy

5.0 (7)

Private Tour Siena San Gimignano and Chianti from Cortona

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$287

Tuscany Landscapes, Castels & Chianti Wine District

Drive through the breathtaking Tuscan countryside along the ancient Cassia Vetus, an old Roman road lined with rolling hills, vineyards, and olive groves. Your journey …More

Florence, Italy

5.0 (2)

Tuscany Landscapes, Castels & Chianti Wine District

Drive through the breathtaking Tuscan countryside along the ancient Cassia Vetus, an old Roman road lined with rolling hills, vineyards, and olive groves. Your journey...

6 hours Free Cancellation

5.0 (2)

from
$396

Umbria like a local: Private Wine Tasting & Dining Experience

This isn’t your average wine tour—it’s a relaxed, hyper-local adventure around one of Umbria’s hidden gems: Lake Trasimeno. What sets us apart is the mix …More

Arezzo, Italy

5.0 (7)

Umbria like a local: Private Wine Tasting & Dining Experience

This isn’t your average wine tour—it’s a relaxed, hyper-local adventure around one of Umbria’s hidden gems: Lake Trasimeno. What sets us apart is the mix...

9 hours

5.0 (7)

from
$793

Lunch in a Tuscan vineyard with wine tasting

Enjoy a unique lunch experience in the picturesque setting of the Poggio ai Laghi vineyard, paired with Wine Tasting and a great Wine Expert who …More

Siena, Italy

5.0 (6)

Lunch in a Tuscan vineyard with wine tasting

Enjoy a unique lunch experience in the picturesque setting of the Poggio ai Laghi vineyard, paired with Wine Tasting and a great Wine Expert who...

2 hours Free Cancellation

5.0 (6)

from
$64

Dinner with wine tasting at Poggio ai Laghi winery

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that …More

Siena, Italy

5.0 (7)

Dinner with wine tasting at Poggio ai Laghi winery

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that...

2 hours Free Cancellation

5.0 (7)

from
$64

Florence: Chianti Classico Private WineTour & Tasting at Gagliole

Most wine tours take you to a winery. This one takes you inside a family. At Gagliole, you will be welcomed personally by the Baer …More

Florence, Italy

4.8 (5)

Florence: Chianti Classico Private WineTour & Tasting at Gagliole

Most wine tours take you to a winery. This one takes you inside a family. At Gagliole, you will be welcomed personally by the Baer...

1 hour 30 minutes Free Cancellation

4.8 (5)

from
$63

Private Chianti Tour from Florence with Lunch and Wine Tasting

Escape Florence for the rolling hills of Chianti on a private tour combing scenic countryside views, Tuscan flavors and local wines. Enjoy round-trip transport in …More

Florence, Italy

5.0 (8)

Private Chianti Tour from Florence with Lunch and Wine Tasting

Escape Florence for the rolling hills of Chianti on a private tour combing scenic countryside views, Tuscan flavors and local wines. Enjoy round-trip transport in...

6 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$443

Montecatini Alto: Cook & Taste Experience

Your experience begins with a welcome drink and a meeting with the Chef, who will guide you through the stories and secrets behind two icons …More

Montecatini Terme, Italy

4.6 (11)

Montecatini Alto: Cook & Taste Experience

Your experience begins with a welcome drink and a meeting with the Chef, who will guide you through the stories and secrets behind two icons...

3 hours 15 minutes Free Cancellation

4.6 (11)

from
$136

Tuscany Wine Tastings with Panoramic View - Florence to Chianti

Whether you’re a group of study abroad students, solo-traveler, or backpacking through Europe, this tour is perfect for anyone looking for an unforgettable wine tasting! …More

Florence, Italy

4.7 (14)

Tuscany Wine Tastings with Panoramic View - Florence to Chianti

Whether you’re a group of study abroad students, solo-traveler, or backpacking through Europe, this tour is perfect for anyone looking for an unforgettable wine tasting!...

5 hours Free Cancellation

4.7 (14)

from
$79

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?