Top Tuscany Wine Tasting & Winery Tours

Q: Got any more Tuscany trip ideas?

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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 →

Florence Wine Tasting Tour with a Private Wine Expert

Discover the purpose of the "little wine holes” in buildings in Florence and taste the best Italian wine on a guided tasting tour! Extended option: …More

Florence, Italy

5.0 (1)

Florence Wine Tasting Tour with a Private Wine Expert

Discover the purpose of the "little wine holes” in buildings in Florence and taste the best Italian wine on a guided tasting tour! Extended option:...

2 to 3 hours Free Cancellation

5.0 (1)

from
$129

Private Chianti Wine Tasting & Scenic Florence Drive Half-Day

Discover the beauty and flavors of Tuscany with a private half-day tour from Florence to the Chianti wine region. Leave Florence with your private driver …More

Florence, Italy

5.0 (1)

Private Chianti Wine Tasting & Scenic Florence Drive Half-Day

Discover the beauty and flavors of Tuscany with a private half-day tour from Florence to the Chianti wine region. Leave Florence with your private driver...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$145

Private Wine & Evo oil Tasting with Vegetarian Meal

✅ Exclusive Wine, Olive Oil & Balsamic Vinegar Tasting – Savor our organic wines and premium olive oils, straight from our estate. ✅ Farm-to-Table Vegetarian …More

San Gimignano, Italy

5.0 (1)

Private Wine & Evo oil Tasting with Vegetarian Meal

✅ Exclusive Wine, Olive Oil & Balsamic Vinegar Tasting – Savor our organic wines and premium olive oils, straight from our estate. ✅ Farm-to-Table Vegetarian...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$86

Ideal for those who want a complete introduction of the estate. You will be guided through an experience that will involve all the senses, in …More

Florence, Italy

5.0 (1)

Cellar Wine Tour

Ideal for those who want a complete introduction of the estate. You will be guided through an experience that will involve all the senses, in...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$34

The ideal path to fully experience the Estate with an exclusive tasting in the wine bar overlooking the vineyards and the surrounding countryside. The Wine …More

Florence, Italy

4.3 (3)

Wine Tour Experience

The ideal path to fully experience the Estate with an exclusive tasting in the wine bar overlooking the vineyards and the surrounding countryside. The Wine...

2 hours Free Cancellation

4.3 (3)

from
$51

Enjoy a day with your local driver-guide exploring one of the most charming area in Tuscany! Volterra is simply magnificent, located on a hilltop and …More

Pisa, Italy

5.0 (1)

Tuscany and Wine Tasting Tour from Pisa

Enjoy a day with your local driver-guide exploring one of the most charming area in Tuscany! Volterra is simply magnificent, located on a hilltop and...

9 hours Hotel pickup offered

5.0 (1)

from
$1,079

TRANSFER TOUR Florence to Rome with a wine experience in MONTEPULCIANO

It's not just arriving at your destination that makes your vacation ... it's experiencing new and wonderful things along the way. Enjoy a very special …More

Florence, Italy

5.0 (1)

TRANSFER TOUR Florence to Rome with a wine experience in MONTEPULCIANO

It's not just arriving at your destination that makes your vacation ... it's experiencing new and wonderful things along the way. Enjoy a very special...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,435

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting, …More

Arezzo, Italy

5.0 (1)

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting,...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$32

Private Tour Of Chianti with Wine Tastings

Spend a unique day in the Tuscan countryside and discover the essence of our region: delicious wine and food, breathtaking views, medieval castles, and unrivaled …More

Florence, Italy

5.0 (1)

Private Tour Of Chianti with Wine Tastings

Spend a unique day in the Tuscan countryside and discover the essence of our region: delicious wine and food, breathtaking views, medieval castles, and unrivaled...

8 hours Hotel pickup offered

5.0 (1)

from
$1,704

The orange Gold of San Gimignano - The Saffron Cooking class

✅ Authentic Saffron Experience – Cook with San Gimignano Saffron DOP, one of Tuscany’s most prized ingredients. ✅ Hands-On Cooking Class – Learn traditional techniques …More

San Gimignano, Italy

5.0 (1)

The orange Gold of San Gimignano - The Saffron Cooking class

✅ Authentic Saffron Experience – Cook with San Gimignano Saffron DOP, one of Tuscany’s most prized ingredients. ✅ Hands-On Cooking Class – Learn traditional techniques...

3 hours Free Cancellation

5.0 (1)

from
$287

Maremma is considered the new Eldorado for its powerful and elegant wines, wild and shining landscapes. The typical local cuisine is Mediterranean. The people of …More

Siena, Italy

5.0 (1)

The Maremma

Maremma is considered the new Eldorado for its powerful and elegant wines, wild and shining landscapes. The typical local cuisine is Mediterranean. The people of...

8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$869

Chianti: eno-excursion through the vineyards

Excursion in the heart of Chianti, among the rolling hills covered with vineyards, olive groves and dotted with villages suspended in time, we will also …More

Chianti, Italy

5.0 (1)

Chianti: eno-excursion through the vineyards

Excursion in the heart of Chianti, among the rolling hills covered with vineyards, olive groves and dotted with villages suspended in time, we will also...

3 to 5 hours Free Cancellation

5.0 (1)

from
$68

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of …More

Siena, Italy

5.0 (1)

Private Grape stomping in Chianti from Siena

Harvest has always been a time of celebration in the countryside: after months of hard work, the ripening of the grapes marks the beginning of...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$278

Cellar tour, Tasting of 6 wines, dish combined typical products

The tasting at Cantalici is a way to immerse yourself in a family atmosphere to discover typical wines of the Chianti Classico production area, an …More

Lucca, Italy

5.0 (1)

Cellar tour, Tasting of 6 wines, dish combined typical products

The tasting at Cantalici is a way to immerse yourself in a family atmosphere to discover typical wines of the Chianti Classico production area, an...

2 hours

5.0 (1)

from
$57

From Livorno: Pisa, San Gimignano and Chianti private tour

When your boat docks at the Livorno Port, don’t waste time at the port. Book a private Tuscany day trip in advance, and head out …More

Livorno, Italy

5.0 (1)

From Livorno: Pisa, San Gimignano and Chianti private tour

When your boat docks at the Livorno Port, don’t waste time at the port. Book a private Tuscany day trip in advance, and head out...

9 hours Free Cancellation

5.0 (1)

from
$201

Private tour of Siena Monteriggioni San Gimignano, Winery, lunch

Our first stop will be in Siena which with its medieval monuments and art treasures is considered a world heritage site by UNESCO. We'll start …More

Florence, Italy

5.0 (1)

Private tour of Siena Monteriggioni San Gimignano, Winery, lunch

Our first stop will be in Siena which with its medieval monuments and art treasures is considered a world heritage site by UNESCO. We'll start...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$239

Wine experience in the Tuscan hills with tasting in Vinci

Immerse yourself in the history of our farm and discover how our wines are made. The experience begins in the vineyard, continues in the cellar …More

Montecatini Terme, Italy

5.0 (1)

Wine experience in the Tuscan hills with tasting in Vinci

Immerse yourself in the history of our farm and discover how our wines are made. The experience begins in the vineyard, continues in the cellar...

2 hours Free Cancellation

5.0 (1)

from
$46

Truffle hunting and lunch experience, with Vinci and winery.

You will try in a lifetime experience and search for truffles with a truffle-hunting dog through the woods of Tuscany in San Miniato. Enjoy traffles …More

Florence, Italy

4.7 (3)

Truffle hunting and lunch experience, with Vinci and winery.

You will try in a lifetime experience and search for truffles with a truffle-hunting dog through the woods of Tuscany in San Miniato. Enjoy traffles...

10 hours Hotel pickup offered Free Cancellation

4.7 (3)

from
$339

Prepare a dinner with the Florentine Countess in her Villa: cooking class

Constanza is a true Florentine lady of noble birth. She lives in 1600 dwelling with husband Giambruno and beautiful daughter Sofia. As she is a …More

Florence, Italy

5.0 (1)

Prepare a dinner with the Florentine Countess in her Villa: cooking class

Constanza is a true Florentine lady of noble birth. She lives in 1600 dwelling with husband Giambruno and beautiful daughter Sofia. As she is a...

4 hours Free Cancellation

5.0 (1)

from
$217

Lucca Private Day Tour 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

Lucca, Italy

5.0 (1)

Lucca Private Day Tour 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 (1)

from
$1,033

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?