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 →

From Florence: Private Via Francigena Tour with Wine Lunch

A full private day on the Via Francigena, the ancient pilgrims' road to Rome, through the most beautiful towns of Tuscany. • Pick-up at your …More

Florence, Italy

5.0 (2)

From Florence: Private Via Francigena Tour with Wine Lunch

A full private day on the Via Francigena, the ancient pilgrims' road to Rome, through the most beautiful towns of Tuscany. • Pick-up at your...

10 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$318

FLORENCE FOOD TOUR:Markets,street food & Florentine T-bone steak!

Unsure how to spend your time? Food or Art? Why not both? This 3,5 hours walking tour is a delicious way to explore the city …More

Florence, Italy

5.0 (1)

FLORENCE FOOD TOUR:Markets,street food & Florentine T-bone steak!

Unsure how to spend your time? Food or Art? Why not both? This 3,5 hours walking tour is a delicious way to explore the city...

3 hours 30 minutes Free Cancellation

5.0 (1)

from
$157

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up …More

San Gimignano, Italy

5.0 (8)

San Gimignano: Chianti wine tasting

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up...

1 hour Free Cancellation

5.0 (8)

from
$34

From Pisa: Private San Gimignano & Chianti Tour with Lunch

A private day from the Pisa area through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or …More

Pisa, Italy

5.0 (2)

From Pisa: Private San Gimignano & Chianti Tour with Lunch

A private day from the Pisa area through the Tuscan hills, with a farm lunch and two wine tastings. • Pickup at your hotel or...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$261

Wine & cheese Lover’s Paradise in hart of Florence

You won't find any other "freedom tasting" in the city. Why choose it? For its dynamism, because you will decide how much to spend and …More

Florence, Italy

5.0 (21)

Wine & cheese Lover’s Paradise in hart of Florence

You won't find any other "freedom tasting" in the city. Why choose it? For its dynamism, because you will decide how much to spend and...

1 hour 30 minutes Free Cancellation

5.0 (21)

from
$64

Winery tours and tastings in Bolgheri with Wine Guide

Enjoy a unique guided wine tour through Bolgheri, one of the most exciting wine regions in Italy. Discover the origins of its renowned Bordeaux blends …More

Livorno, Italy

5.0 (24)

Winery tours and tastings in Bolgheri with Wine Guide

Enjoy a unique guided wine tour through Bolgheri, one of the most exciting wine regions in Italy. Discover the origins of its renowned Bordeaux blends...

4 to 5 hours Free Cancellation

5.0 (24)

from
$144

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello …More

Siena, Italy

5.0 (3)

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$261

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

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small …More

Siena, Italy

5.0 (35)

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small...

8 hours Hotel pickup offered

5.0 (35)

from
$194

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at …More

Siena, Italy

5.0 (4)

From Siena: Private Volterra, San Gimignano & Wine Lunch

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$272

Private Chianti Afternoon Wine Tour with 2 Family-Run Wineries

A relaxed private afternoon in the Chianti Classico hills, visiting two small family-run wineries that really make their own wine. • Pick-up at your hotel, …More

Florence, Italy

5.0 (9)

Private Chianti Afternoon Wine Tour with 2 Family-Run Wineries

A relaxed private afternoon in the Chianti Classico hills, visiting two small family-run wineries that really make their own wine. • Pick-up at your hotel,...

5 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$125

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up …More

Florence, Italy

5.0 (2)

From Florence: Private Volterra, San Gimignano & Wine Lunch

A private day from Florence to two of the most beautiful hill towns of Tuscany, with a wine lunch at a family-run farm. • Pick-up...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$261

Arezzo: Wine Tasting Experience in Valdichiana area

Enjoy 2 hours wine tasting experience in an elegant and exclusive location, an ancient Tuscan villa located in Valdichiana, in the heart of Tuscany. Together …More

Arezzo, Italy

4.9 (8)

Arezzo: Wine Tasting Experience in Valdichiana area

Enjoy 2 hours wine tasting experience in an elegant and exclusive location, an ancient Tuscan villa located in Valdichiana, in the heart of Tuscany. Together...

2 hours Free Cancellation

4.9 (8)

from
$45

1h30m Wine Tasting and Visit to Val D'Orcia

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del …More

Chianciano Terme, Italy

5.0 (26)

1h30m Wine Tasting and Visit to Val D'Orcia

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del...

1 hour 30 minutes Free Cancellation

5.0 (26)

from
$57

From Pisa: Private Chianti & San Gimignano with Wine Lunch

Spend a day in the iconic landscape of the Chianti hills with a private tour from the Pisa countryside. Drive along avenues of cypress trees, …More

Pisa, Italy

5.0 (4)

From Pisa: Private Chianti & San Gimignano with Wine Lunch

Spend a day in the iconic landscape of the Chianti hills with a private tour from the Pisa countryside. Drive along avenues of cypress trees,...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$250

Chianti Wine and Vinci half day Small Group Tour from Lucca

Experience a relaxed afternoon in the Chianti area with a visit to a boutique winery and enjoy a guided Chianti wine tasting along with a …More

Lucca, Italy

5.0 (25)

Chianti Wine and Vinci half day Small Group Tour from Lucca

Experience a relaxed afternoon in the Chianti area with a visit to a boutique winery and enjoy a guided Chianti wine tasting along with a...

5 hours 30 minutes Free Cancellation

5.0 (25)

from
$147

Private Tuscan meal with Wine and EVO oil tasting

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 (35)

Private Tuscan meal with Wine and EVO oil tasting

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 (35)

from
$78

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

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine Tour

Heart of Chianti Classico - 2 Wineries and Lunch - Chianti Wine Tour Tour Length: 7/8 hours. Dates: Every season. Departure Point: From your accommodation …More

Florence, Italy

5.0 (34)

Heart of Chianti Classico - 2 Wineries Lunch included - Chianti Wine Tour

Heart of Chianti Classico - 2 Wineries and Lunch - Chianti Wine Tour Tour Length: 7/8 hours. Dates: Every season. Departure Point: From your accommodation...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$320

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced …More

Florence, Italy

5.0 (34)

Chianti Wine Tour - Private Wine experience in Tuscany Countryside

Dive into an unparalleled wine journey with our exclusive Chianti Wine Tour, starting directly from your accommodation. Onboard our luxury vehicles, driven by an experienced...

8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$341

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?