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 →

Don’t like to wake up early in the morning? Well, this tour is perfect for you! You will leave Florence in the early afternoon and …More

Florence, Italy

4.2 (314)

Afternoon In Siena And Chianti Dinner

Don’t like to wake up early in the morning? Well, this tour is perfect for you! You will leave Florence in the early afternoon and...

7 hours 30 minutes Free Cancellation

4.2 (314)

from
$102

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion …More

Siena, Italy

4.1 (94)

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion...

10 to 11 hours Free Cancellation

4.1 (94)

from
$125

Florence Wine tour at Sunset with Wine window

Our Florence wine tour will take you to discover one of the city's historic neighborhoods, the Oltrarno. Here, you'll experience authentic Florentine life, away from …More

Florence, Italy

4.2 (59)

Florence Wine tour at Sunset with Wine window

Our Florence wine tour will take you to discover one of the city's historic neighborhoods, the Oltrarno. Here, you'll experience authentic Florentine life, away from...

2 hours Free Cancellation

4.2 (59)

from
$164

Montepulciano: Wine Tasting & Lunch in a typical winery

Enjoy an exclusive wine tasting combined with a typical Tuscan lunch in an ancient wine cellar in the heart of Montepulciano. ATTENTION: From 06th August …More

Montepulciano, Italy

4.1 (37)

Montepulciano: Wine Tasting & Lunch in a typical winery

Enjoy an exclusive wine tasting combined with a typical Tuscan lunch in an ancient wine cellar in the heart of Montepulciano. ATTENTION: From 06th August...

1 hour 30 minutes Free Cancellation

4.1 (37)

from
$65

Nestled in the Chianti hills, visit the estate, whose villa is the historical testimony of a history dating back to the year 1000, and taste …More

Siena, Italy

3.8 (25)

Chianti Classico wine Tour and Tasting

Nestled in the Chianti hills, visit the estate, whose villa is the historical testimony of a history dating back to the year 1000, and taste...

1 hour 30 minutes Free Cancellation

3.8 (25)

from
$67

Historic Castle & Brunello Wine Experience in Montalcino

Step inside a historic castle estate in the heart of the prestigious Brunello di Montalcino wine region and discover over 600 years of Tuscan winemaking …More

Siena, Italy

4.1 (22)

Historic Castle & Brunello Wine Experience in Montalcino

Step inside a historic castle estate in the heart of the prestigious Brunello di Montalcino wine region and discover over 600 years of Tuscan winemaking...

1 hour Free Cancellation

4.1 (22)

from
$44

Tour of the historical cellars in Montepulciano

Montepulciano is famous for its cellars in the historical center, something that you do not have the chance to visit elsewhere. During your visit at …More

Montepulciano, Italy

4.3 (16)

Tour of the historical cellars in Montepulciano

Montepulciano is famous for its cellars in the historical center, something that you do not have the chance to visit elsewhere. During your visit at...

2 hours 30 minutes Free Cancellation

4.3 (16)

from
$90

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation …More

Siena, Italy

4.1 (15)

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation...

1 hour 45 minutes Free Cancellation

4.1 (15)

from
$80

Gourmet tour in the Montepulciano old town center

Explore Montepulciano like a local on a relaxed food and wine walking tour through the historic center. Enjoy stunning views, medieval streets, and the authentic …More

Montepulciano, Italy

4.1 (10)

Gourmet tour in the Montepulciano old town center

Explore Montepulciano like a local on a relaxed food and wine walking tour through the historic center. Enjoy stunning views, medieval streets, and the authentic...

3 hours Free Cancellation

4.1 (10)

from
$154

Valle del Sole Tasting of 3 wines and EVO oil

A fantastic Wine Tasting on our terrace, where you can see all our vineyards directly, while tasting 3 of our biodynamic wines, a white wine, …More

Lucca, Italy

3.8 (10)

Valle del Sole Tasting of 3 wines and EVO oil

A fantastic Wine Tasting on our terrace, where you can see all our vineyards directly, while tasting 3 of our biodynamic wines, a white wine,...

1 hour Free Cancellation

3.8 (10)

from
$40

Private wine, Extra Virgin Olive Oils & Cheese Tasting

Indulge in the authentic flavors of Tuscany with this exclusive wine, olive oil & balsamic vinegar tasting experience just minutes from the heart of San …More

San Gimignano, Italy

4.0 (9)

Private wine, Extra Virgin Olive Oils & Cheese Tasting

Indulge in the authentic flavors of Tuscany with this exclusive wine, olive oil & balsamic vinegar tasting experience just minutes from the heart of San...

45 minutes Free Cancellation

4.0 (9)

from
$63

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

Upon your arrival we will welcome you to visit the winery and discover all the winemaking processes together. After the visit we will reach the …More

Montepulciano, Italy

4.3 (8)

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

Upon your arrival we will welcome you to visit the winery and discover all the winemaking processes together. After the visit we will reach the...

4 hours

4.3 (8)

from
$114

Special Chianti Afternoon Wine Tour from Florence

Embark on an unforgettable journey through the heart of Tuscany on our exclusive Chianti Wine Tour. This experience is not just a tour, but a …More

Florence, Italy

3.9 (8)

Special Chianti Afternoon Wine Tour from Florence

Embark on an unforgettable journey through the heart of Tuscany on our exclusive Chianti Wine Tour. This experience is not just a tour, but a...

5 hours 30 minutes Free Cancellation

3.9 (8)

from
$107

The Complete Wine Tour Brunello, Nobile, Chianti wine experience

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this 10-hour private excursion from Florence. Enjoy 2 or 3 different regional varieties: …More

Florence, Italy

4.0 (7)

The Complete Wine Tour Brunello, Nobile, Chianti wine experience

Get a personalized tour of Montalcino, Montepulciano, and the Chianti region during this 10-hour private excursion from Florence. Enjoy 2 or 3 different regional varieties:...

10 hours Free Cancellation

4.0 (7)

from
$272

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and …More

Chianti, Italy

4.2 (6)

Montalcino wine tour

A unique way to discover the colours, the landscapes, to taste the flavours of this land, come and meet the producers, enojoy the wines, and...

9 hours

4.2 (6)

from
$397

Florence Ghost & Crime Small-Group Tour with Tasting & Wine

Discover Florence’s darker side on a guided walking tour filled with true crime, legends, and hidden stories. Walk through the city’s ancient streets as your …More

Florence, Italy

4.2 (6)

Florence Ghost & Crime Small-Group Tour with Tasting & Wine

Discover Florence’s darker side on a guided walking tour filled with true crime, legends, and hidden stories. Walk through the city’s ancient streets as your...

2 hours Free Cancellation

4.2 (6)

from
$44

Half-Day Chianti Wine and Olive Oil Tour from Viareggio

The best way to enjoy a Chianti Wine tasting in Tuscany. Our small group sizes mean a more intimate and fun Tuscan Wine experience for …More

Versilia, Italy

4.2 (5)

Half-Day Chianti Wine and Olive Oil Tour from Viareggio

The best way to enjoy a Chianti Wine tasting in Tuscany. Our small group sizes mean a more intimate and fun Tuscan Wine experience for...

6 hours Free Cancellation

4.2 (5)

from
$159

Wellbeing landscapes: Fonteverde Spa in San Casciano dei Bagni

Landscapes of wellbeing: an exclusive couple experience enjoying the landscapes of wellbeing, the Spa “Fonteverde” and typical products tasting or aperitif. …More

San Casciano dei Bagni, Italy

4.3 (4)

Wellbeing landscapes: Fonteverde Spa in San Casciano dei Bagni

Landscapes of wellbeing: an exclusive couple experience enjoying the landscapes of wellbeing, the Spa “Fonteverde” and typical products tasting or aperitif....

6 hours Free Cancellation

4.3 (4)

from
$101

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as …More

Siena, Italy

4.0 (3)

Private Montalcino and Pienza Tour from Siena

Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as...

6 hours Hotel pickup offered Free Cancellation

4.0 (3)

from
$321

Taste of Tuscany San Gimignano Winery with Transfer from Florence

TOUR HIGHLIGHTS • Sample at least eleven spectacular wines, a selection of local cheeses and traditional foods and recipes of Tuscany • Benefit from a …More

Florence, Italy

4.0 (2)

Taste of Tuscany San Gimignano Winery with Transfer from Florence

TOUR HIGHLIGHTS • Sample at least eleven spectacular wines, a selection of local cheeses and traditional foods and recipes of Tuscany • Benefit from a...

4 hours Free Cancellation

4.0 (2)

from
$216

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?