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 →

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

What’s more Tuscan than a plate of cold-cuts and a glass of wine? After visiting the property and the old cellar, the experience goes on …More

Montepulciano, Italy

5.0 (7)

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

What’s more Tuscan than a plate of cold-cuts and a glass of wine? After visiting the property and the old cellar, the experience goes on...

1 hour 15 minutes Free Cancellation

5.0 (7)

from
$51

The only authentic wine tour in Pisa. Visit two real tuscan organic wineries. We are talking about two historical places with two different ways of …More

Pisa, Italy

5.0 (7)

Tuscan Wine Tour in Pisa by van

The only authentic wine tour in Pisa. Visit two real tuscan organic wineries. We are talking about two historical places with two different ways of...

6 hours Free Cancellation

5.0 (7)

from
$183

Chianti Lovers Tour- 2 Wineries and SuperTuscan Small Group from Lucca

Experience in wine for Chianti Lovers. Visit 2 wineries in the Chianti area. Visit cellar, walk in the vineyards and taste very good wine …More

Lucca, Italy

5.0 (7)

Chianti Lovers Tour- 2 Wineries and SuperTuscan Small Group from Lucca

Experience in wine for Chianti Lovers. Visit 2 wineries in the Chianti area. Visit cellar, walk in the vineyards and taste very good wine...

6 hours Free Cancellation

5.0 (7)

from
$170

Pasta & Tiramisu Cooking Class + Italian Market Tour in Florence

This cooking class stands out by offering an authentic and immersive experience in the heart of Florence. You’ll start your culinary adventure with a guided …More

Florence, Italy

5.0 (7)

Pasta & Tiramisu Cooking Class + Italian Market Tour in Florence

This cooking class stands out by offering an authentic and immersive experience in the heart of Florence. You’ll start your culinary adventure with a guided...

4 hours 30 minutes Free Cancellation

5.0 (7)

from
$159

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

Private Chianti Wine Tour from Florence: 2 Wineries Private Tour

Discover the many delights of Tuscany’s wine on this private wine and food tasting tour. You will visit 2 top-rated wineries: historical castle with 900-years …More

Florence, Italy

5.0 (7)

Private Chianti Wine Tour from Florence: 2 Wineries Private Tour

Discover the many delights of Tuscany’s wine on this private wine and food tasting tour. You will visit 2 top-rated wineries: historical castle with 900-years...

5 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$375

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in …More

Siena, Italy

5.0 (7)

San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from SIENA

* Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Siena * Private and exclusive service * 8 hours in...

8 hours Hotel pickup offered

5.0 (7)

from
$193

Would you like to play golf in the center of Florence? Do you want to have a little break from museums, from long lines, from …More

Florence, Italy

5.0 (7)

Golf and wine: in the heart of Florence

Would you like to play golf in the center of Florence? Do you want to have a little break from museums, from long lines, from...

6 hours Free Cancellation

5.0 (7)

from
$436

Embark on a memorable journey through Florence that combines the timeless charm of its old wooden boats with the delight of sipping exquisite wine. As …More

Florence, Italy

5.0 (7)

Panoramic Florence by Boat with Wine

Embark on a memorable journey through Florence that combines the timeless charm of its old wooden boats with the delight of sipping exquisite wine. As...

1 hour

5.0 (7)

from
$75

Siena, San Gimignano and Chianti Wine Small Group from Viareggio

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in …More

Versilia, Italy

5.0 (7)

Siena, San Gimignano and Chianti Wine Small Group from Viareggio

Enjoy the visit of the most beautiful medieval villages in Tuscany with us: Siena and San Gimignano. Admire the lovely and stunning views driving in...

11 hours 30 minutes Free Cancellation

5.0 (7)

from
$211

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

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

Tuscan Pasta & Wine Experience in San Gimignano: Cook & Taste

Discover the secrets of Italian pasta-making in this immersive Fresh Pasta Cooking Class in San Gimignano. In a stunning Tuscan winery, you’ll learn how to …More

San Gimignano, Italy

4.8 (6)

Tuscan Pasta & Wine Experience in San Gimignano: Cook & Taste

Discover the secrets of Italian pasta-making in this immersive Fresh Pasta Cooking Class in San Gimignano. In a stunning Tuscan winery, you’ll learn how to...

3 hours Free Cancellation

4.8 (6)

from
$215

Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging …More

Chianti, Italy

5.0 (6)

Wine Tasting of Brunello with Tuscan Cold Cuts and Cheese

Enjoy an exclusive one-hour wine tasting experience featuring warm homemade bread and exquisite Tuscan olive oil. Take a leisurely stroll through the vineyard before indulging...

1 hour 30 minutes Free Cancellation

5.0 (6)

from
$45

Private Half Day Tour Chianti Classico Wine Experience

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to a breathtaking visit of ancient vineyards and medieval villages in the famous landscapes of …More

Florence, Italy

5.0 (6)

Private Half Day Tour Chianti Classico Wine Experience

• EXPERIENCE FOR YOUR PRIVATE GROUP • Dedicate one day to a breathtaking visit of ancient vineyards and medieval villages in the famous landscapes of...

5 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$103

1-Hour Guided Tuscan Wine Tasting in Florence

All wines for the experience are exclusive in Florence and not exported outside Italy; very small production wineries, organic, biodynamic, or natural. A pure, genuine, …More

Florence, Italy

5.0 (6)

1-Hour Guided Tuscan Wine Tasting in Florence

All wines for the experience are exclusive in Florence and not exported outside Italy; very small production wineries, organic, biodynamic, or natural. A pure, genuine,...

1 hour Free Cancellation

5.0 (6)

from
$80

Discover the heart of Florence, where history, art, and cuisine intertwine. Our adventure begins in San Lorenzo, a district filled with the Central Market and …More

Florence, Italy

5.0 (6)

Private Food Tour In Florence

Discover the heart of Florence, where history, art, and cuisine intertwine. Our adventure begins in San Lorenzo, a district filled with the Central Market and...

3 hours Free Cancellation

5.0 (6)

from
$142

Paint and Wine Experience with Ponte Vecchio View

With a front-row view of the iconic Ponte Vecchio, this Paint and Wine experience is unlike any other in Florence. Set in a charming studio …More

Florence, Italy

4.8 (6)

Paint and Wine Experience with Ponte Vecchio View

With a front-row view of the iconic Ponte Vecchio, this Paint and Wine experience is unlike any other in Florence. Set in a charming studio...

2 hours Free Cancellation

4.8 (6)

from
$68

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

Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is …More

San Gimignano, Italy

4.8 (6)

Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is...

1 hour 30 minutes Free Cancellation

4.8 (6)

from
$109

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Tuscany Wine Tasting & Winery Tours are:

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?