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 →

Pisa, Siena, San Gimignano Small Group with Lunch & Wine Tasting

Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a …More

Florence, Italy

4.8 (47)

Pisa, Siena, San Gimignano Small Group with Lunch & Wine Tasting

Discover the highlights of Tuscany on a small group tour from Florence, visiting Siena, San Gimignano, and Pisa. Travel in a cozy atmosphere with a...

11 hours 30 minutes Free Cancellation

4.8 (47)

from
$181

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

This E-bike Chianti & Tuscany tour in the famous Chianti Classico countryside will take you away from the crowds and noise of Florence, learn about …More

Florence, Italy

5.0 (56)

E-bike Chianti Classico Tuscany Tour with Wine and Lunch at Farm

This E-bike Chianti & Tuscany tour in the famous Chianti Classico countryside will take you away from the crowds and noise of Florence, learn about...

7 hours Free Cancellation

5.0 (56)

from
$181

Small group Chianti-side wine tour with Mercedes V class Van

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will visit two not "commercial" wineries, with …More

Florence, Italy

5.0 (43)

Small group Chianti-side wine tour with Mercedes V class Van

Our tour is made with passion by expert english speaking drivers who know everything about the area. We will visit two not "commercial" wineries, with...

5 hours Free Cancellation

5.0 (43)

from
$276

Full immersion in the world of wine. The experience is created for those who want to get closer to the Tuscan tradition of producing of …More

San Gimignano, Italy

4.8 (56)

5 Wine Tastings in San Gimignano

Full immersion in the world of wine. The experience is created for those who want to get closer to the Tuscan tradition of producing of...

2 hours Free Cancellation

4.8 (56)

from
$75

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the …More

Florence, Italy

4.9 (477)

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

Explore the Tuscan countryside in a most delightful way... on horseback! This horse riding adventure requires absolutely no prior experience and will give you the...

7 hours Free Cancellation

4.9 (477)

from
$217

Private Tour: Chianti Region Tour by Minivan

Escape from the city traffic to enjoy a lovely day in the Chianti wine region with stop in a small winery for lunch and wine …More

Florence, Italy

5.0 (25)

Private Tour: Chianti Region Tour by Minivan

Escape from the city traffic to enjoy a lovely day in the Chianti wine region with stop in a small winery for lunch and wine...

8 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$848

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards …More

Siena, Italy

4.5 (125)

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards...

11 hours Free Cancellation

4.5 (125)

from
$177

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by …More

Florence, Italy

5.0 (41)

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by...

11 hours Free Cancellation

5.0 (41)

from
$178

Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti

Experience Chianti like a true Italian icon. Sit back and relax as your professional private driver takes you through the most scenic roads around Chianti …More

San Gimignano, Italy

4.6 (38)

Vintage Fiat 500 Tour: Lunch and 2 Wine tastings in the Chianti

Experience Chianti like a true Italian icon. Sit back and relax as your professional private driver takes you through the most scenic roads around Chianti...

7 hours Free Cancellation

4.6 (38)

from
$170

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti …More

Siena, Italy

5.0 (20)

Siena: Chianti Wine Tour with Wine Tasting and Lunch

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti...

3 hours Free Cancellation

5.0 (20)

from
$85

Guided Walking Tour of Florence with Food & Wine Tastings

Taste Florence like a local on this guided food and wine walking tour. Stroll through the city’s most iconic squares while uncovering authentic flavors, hidden …More

Florence, Italy

5.0 (26)

Guided Walking Tour of Florence with Food & Wine Tastings

Taste Florence like a local on this guided food and wine walking tour. Stroll through the city’s most iconic squares while uncovering authentic flavors, hidden...

2 hours Free Cancellation

5.0 (26)

from
$136

Fresh Pasta Class in Florence with unlimited Wine

Step into history as you join our class held in one of the oldest restaurants in Florence, nestled within a stunning building that dates back …More

Florence, Italy

4.9 (20)

Fresh Pasta Class in Florence with unlimited Wine

Step into history as you join our class held in one of the oldest restaurants in Florence, nestled within a stunning building that dates back...

3 hours 15 minutes Free Cancellation

4.9 (20)

from
$67

Val d’Orcia Wine Tour with Lunch & Brunello from Florence

Immerse yourself in a day of art, culture, and wine. Ready for an unforgettable journey in Tuscany's breathtaking Val d'Orcia region. Taste Brunello wine, explore …More

Florence, Italy

4.3 (84)

Val d’Orcia Wine Tour with Lunch & Brunello from Florence

Immerse yourself in a day of art, culture, and wine. Ready for an unforgettable journey in Tuscany's breathtaking Val d'Orcia region. Taste Brunello wine, explore...

12 hours Free Cancellation

4.3 (84)

from
$135

Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with …More

Siena, Italy

4.9 (108)

Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with...

8 hours Hotel pickup offered Free Cancellation

4.9 (108)

from
$261

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own …More

Florence, Italy

4.8 (29)

Private Pisa and Lucca Wine Tour from Florence

Leave Florence and discover the Tuscan cities of Lucca and Pisa on a day trip. You’ll see the UNESCO-listed Leaning Tower of Pisa (entry own...

8 hours Free Cancellation

4.8 (29)

from
$201

Chianti Classico and Super Tuscan 3 Winery Tour

This tour goes in the famous Chianti wine growing region, to taste Chianti e Super Tuscan wines, lunch in a small boutique of wine. …More

Florence, Italy

5.0 (125)

Chianti Classico and Super Tuscan 3 Winery Tour

This tour goes in the famous Chianti wine growing region, to taste Chianti e Super Tuscan wines, lunch in a small boutique of wine....

7 hours

5.0 (125)

from
$331

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

Pisa guided tour and Wine tasting with Leaning Tower ticket

Small groups! Discover the Miracle Square and taste the Tuscan flavours with this amazing tour that will show you the best of Pisa. With your …More

Pisa, Italy

4.5 (35)

Pisa guided tour and Wine tasting with Leaning Tower ticket

Small groups! Discover the Miracle Square and taste the Tuscan flavours with this amazing tour that will show you the best of Pisa. With your...

2 hours 30 minutes Free Cancellation

4.5 (35)

from
$90

Experience Chianti & Cheese w/ 3 wineries & dairy visit—max 8 pp

We meet in central Florence at our Grape Tours office, please be around 15 minutes early to check in. In a small group of min …More

Florence, Italy

4.9 (146)

Experience Chianti & Cheese w/ 3 wineries & dairy visit—max 8 pp

We meet in central Florence at our Grape Tours office, please be around 15 minutes early to check in. In a small group of min...

7 hours

4.9 (146)

from
$320

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
$453

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:

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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?