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 →

Small-Group Florence Vespa Passenger Ride with Wine Window

Embark on a delightful journey through the heart of Florence and its surrounding countryside as a passenger on a classic Vespa. This guided experience lets …More

Florence, Italy

5.0 (37)

Small-Group Florence Vespa Passenger Ride with Wine Window

Embark on a delightful journey through the heart of Florence and its surrounding countryside as a passenger on a classic Vespa. This guided experience lets...

1 hour 30 minutes Free Cancellation

5.0 (37)

from
$136

Lucca tour and Pisa Tower + WineTasting by van from Livorno Port

We have to tell you: we have a soft spot for this special city. It is a magical place, that still maintains that authenticity and …More

Livorno, Italy

4.9 (36)

Lucca tour and Pisa Tower + WineTasting by van from Livorno Port

We have to tell you: we have a soft spot for this special city. It is a magical place, that still maintains that authenticity and...

7 to 8 hours Free Cancellation

4.9 (36)

from
$159

Pisa Pasta Cooking Class (Private Experience)

Join a hands-on pasta cooking class near Pisa, where you’ll learn how to make fresh Italian pasta from scratch using traditional techniques passed down through …More

5.0 (36)

Pisa Pasta Cooking Class (Private Experience)

Join a hands-on pasta cooking class near Pisa, where you’ll learn how to make fresh Italian pasta from scratch using traditional techniques passed down through...

3 hours 30 minutes Free Cancellation

5.0 (36)

from
$148

At Vini di Toscana we organize private tours for small and big groups. Each tour includes the visit to our cellars and vineyard in the …More

Arezzo, Italy

5.0 (36)

Cellar Tour & Wine Tasting

At Vini di Toscana we organize private tours for small and big groups. Each tour includes the visit to our cellars and vineyard in the...

3 hours Free Cancellation

5.0 (36)

from
$57

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

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

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and …More

Florence, Italy

5.0 (35)

Quad Tour ATV Adventure in Chianti. Lunch and Wine Tasting

Come and discover the wild heart of Chianti, together with us you can live an experience totally immersed in the green of the countryside and...

6 to 8 hours Free Cancellation

5.0 (35)

from
$367

Private Day Trip Wine Experience with lunch in Chianti Classico

• EXPERIENCE FOR YOUR PRIVATE GROUP • Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from …More

Florence, Italy

5.0 (34)

Private Day Trip Wine Experience with lunch in Chianti Classico

• EXPERIENCE FOR YOUR PRIVATE GROUP • Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$140

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your …More

Florence, Italy

5.0 (34)

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your...

8 hours Hotel pickup offered Free Cancellation

5.0 (34)

from
$454

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

Chianti Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit …More

Montecatini Terme, Italy

5.0 (34)

Chianti Wine and Vinci half day Small Group Tour from Montecatini Terme

Experience a relaxed afternoon in the Chianti area with a special visit to a boutique winery. Enjoy our guided Chianti Wine tasting and a visit...

4 hours 30 minutes Free Cancellation

5.0 (34)

from
$136

Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit two wineries in Chianti and San Gimignano, with a 15-minute …More

Florence, Italy

5.0 (33)

Chianti Wine Tour from Florence to San Gimignano with 2 Wineries

Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit two wineries in Chianti and San Gimignano, with a 15-minute...

7 to 8 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$134

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Experience an unforgettable full-day chauffeur-driven adventure deep in the heart of Chianti — far from the hustle and bustle of Florence. Sit back and relax …More

Florence, Italy

4.9 (33)

Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

Experience an unforgettable full-day chauffeur-driven adventure deep in the heart of Chianti — far from the hustle and bustle of Florence. Sit back and relax...

8 hours Hotel pickup offered Free Cancellation

4.9 (33)

from
$120

Wine Windows Walk with Wine Tasting and Appetizers

- Admire beautiful Medieval and Renaissance landmark sites walking through the city - Discover the famous wine windows in the historical center and enjoy a …More

Florence, Italy

4.9 (32)

Wine Windows Walk with Wine Tasting and Appetizers

- Admire beautiful Medieval and Renaissance landmark sites walking through the city - Discover the famous wine windows in the historical center and enjoy a...

2 hours 30 minutes Free Cancellation

4.9 (32)

from
$101

Mercato di Centrale - Food and Wine Tasting Highlights Tour

Experience the culinary delights and rich history of Florence, Italy, on our immersive 3.5-hour food tour. Wander through the charming streets and iconic squares of …More

Florence, Italy

5.0 (32)

Mercato di Centrale - Food and Wine Tasting Highlights Tour

Experience the culinary delights and rich history of Florence, Italy, on our immersive 3.5-hour food tour. Wander through the charming streets and iconic squares of...

3 hours 30 minutes Free Cancellation

5.0 (32)

from
$102

PRIVATE Hands-On Cooking Class & Wine in Mirella’s Florence Home

Rather than yet another dinner out on the town, enjoy an intimate, private cooking experience in the south Florence town of Antella. The ultimate take-home …More

Florence, Italy

5.0 (31)

PRIVATE Hands-On Cooking Class & Wine in Mirella’s Florence Home

Rather than yet another dinner out on the town, enjoy an intimate, private cooking experience in the south Florence town of Antella. The ultimate take-home...

3 hours Free Cancellation

5.0 (31)

from
$269

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is …More

Florence, Italy

5.0 (31)

Private Chianti Safari: Off Road Tuscany Wine Tour with Lunch from Florence

For connoisseurs and amateurs alike, there’s no better way to explore the famous Chianti vineyards and sample the world-class tipples for which the area is...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$560

Small group Chianti Classico & Brunello wine region from Siena

This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you …More

Siena, Italy

4.9 (31)

Small group Chianti Classico & Brunello wine region from Siena

This is a semi-private which means a maximum of 6 people in tour, so you will have a private vehicle and all the attention you...

5 hours 30 minutes Free Cancellation

4.9 (31)

from
$205

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those …More

Florence, Italy

5.0 (31)

A Journey Across Tuscany’s History, Olive Oil Heritage and Beauty

Experience of some groups thrugh myself: What a beautiful day just south of Florence visiting the American World War II Memorial and Cemetery for those...

8 hours Hotel pickup offered Free Cancellation

5.0 (31)

from
$172

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?