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 →

San Gimignano and Winery Experience with Lunch from Livorno

If you wish to get to know more about Tuscany, visit a beautiful medieval town and get to taste the wine and the local dishes …More

Livorno, Italy

5.0 (4)

San Gimignano and Winery Experience with Lunch from Livorno

If you wish to get to know more about Tuscany, visit a beautiful medieval town and get to taste the wine and the local dishes...

7 to 8 hours Free Cancellation

5.0 (4)

from
$169

Pedal your way through the panoramic landscapes of Tuscany on a bike tour that’s suitable for all experience levels. Take it slow to soak up …More

Florence, Italy

4.6 (24)

Full-Day Tuscan Countryside Bike Tour

Pedal your way through the panoramic landscapes of Tuscany on a bike tour that’s suitable for all experience levels. Take it slow to soak up...

4 hours 30 minutes Free Cancellation

4.6 (24)

from
$169

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will …More

Florence, Italy

4.9 (10)

Private Tour: Medieval Val d'Orcia by Minivan from Florence

Leaving from Florence, this 9-hours tour by air-conditioned minivan will let you dive into the breathtaking and delicate Val d'Orcia. In this valley you will...

9 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$165

Truffle Lunch & Hunting Experience in San Gimignano

Join an authentic truffle hunting and experience the thrill of finding, smelling, and touching one of nature’s rarest treasures. Led by expert truffle hunters Mirco …More

San Gimignano, Italy

4.9 (44)

Truffle Lunch & Hunting Experience in San Gimignano

Join an authentic truffle hunting and experience the thrill of finding, smelling, and touching one of nature’s rarest treasures. Led by expert truffle hunters Mirco...

3 hours Free Cancellation

4.9 (44)

from
$224

Fabulous Tuscany—organic wine & cheese tour—max 8 pp

We meet at our Grape Tours office 15 minutes prior to departure time and you will meet your knowledgeable guide. After a half-hour beautiful ride …More

Florence, Italy

4.9 (55)

Fabulous Tuscany—organic wine & cheese tour—max 8 pp

We meet at our Grape Tours office 15 minutes prior to departure time and you will meet your knowledgeable guide. After a half-hour beautiful ride...

7 hours

4.9 (55)

from
$295

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
$45

From Florence: Chianti Wine Tour with Tastings & San Gimignano

Escape the city for a memorable morning in the heart of Chianti. Departing from Florence, travel through rolling Tuscan hills dotted with vineyards and olive …More

Florence, Italy

4.4 (13)

From Florence: Chianti Wine Tour with Tastings & San Gimignano

Escape the city for a memorable morning in the heart of Chianti. Departing from Florence, travel through rolling Tuscan hills dotted with vineyards and olive...

5 hours 30 minutes Free Cancellation

4.4 (13)

from
$56

Private Chianti Wine Tasting & Brolio Castle Experience

Embark on a private adventure through the beautiful Chianti wine region, accompanied by an expert local guide and driver in an exclusive vehicle. Begin at …More

Florence, Italy

4.8 (5)

Private Chianti Wine Tasting & Brolio Castle Experience

Embark on a private adventure through the beautiful Chianti wine region, accompanied by an expert local guide and driver in an exclusive vehicle. Begin at...

8 hours Free Cancellation

4.8 (5)

from
$426

Premium Wine Tasting with Tuscan Flavours

Between Chianti and Crete Senesi, a few minutes from Siena, San Giorgio a Lapi offers a Premium Wine Tasting dedicated to those who want to …More

Siena, Italy

5.0 (2)

Premium Wine Tasting with Tuscan Flavours

Between Chianti and Crete Senesi, a few minutes from Siena, San Giorgio a Lapi offers a Premium Wine Tasting dedicated to those who want to...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$37

A Classic Tuscan Winery with Lunch in Montepulciano

Stop and savor Tuscany, tasting our wines, enjoying a light lunch and the typical flavors of this region. You will visit a hundred-year old wine …More

Montepulciano, Italy

5.0 (3)

A Classic Tuscan Winery with Lunch in Montepulciano

Stop and savor Tuscany, tasting our wines, enjoying a light lunch and the typical flavors of this region. You will visit a hundred-year old wine...

1 hour 45 minutes Free Cancellation

5.0 (3)

from
$102

From Florence The Immersive Tuscan Winery Experience

Your experience begins with a warm welcome and a guided tour through the scenic vineyard, nestled among the rolling hills. As you stroll between the …More

Florence, Italy

5.0 (2)

From Florence The Immersive Tuscan Winery Experience

Your experience begins with a warm welcome and a guided tour through the scenic vineyard, nestled among the rolling hills. As you stroll between the...

3 to 4 hours Free Cancellation

5.0 (2)

from
$157

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and …More

Siena, Italy

4.8 (8)

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and...

10 to 11 hours Free Cancellation

4.8 (8)

from
$261

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in …More

Siena, Italy

4.8 (10)

Chianti Half Day Wine Tasting Tour from Siena

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in...

5 hours Free Cancellation

4.8 (10)

from
$56

Cities, Cheese and Wine Tour in Pienza & Montepulciano

Pienza and Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including …More

Siena, Italy

4.9 (25)

Cities, Cheese and Wine Tour in Pienza & Montepulciano

Pienza and Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (25)

from
$330

Chianti Vineyards Tours in Private Luxury Van from Florence

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent …More

Florence, Italy

5.0 (20)

Chianti Vineyards Tours in Private Luxury Van from Florence

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent...

8 hours Hotel pickup offered Free Cancellation

5.0 (20)

from
$815

Exclusive lunch, Winery tour, Organic wines in Chianti Classico

Immerse yourself in the beauty of the Tuscan countryside of Panzanello. You will be fascinated by the spectacle of the cypress trees that will accompany …More

Florence, Italy

5.0 (8)

Exclusive lunch, Winery tour, Organic wines in Chianti Classico

Immerse yourself in the beauty of the Tuscan countryside of Panzanello. You will be fascinated by the spectacle of the cypress trees that will accompany...

2 to 3 hours Free Cancellation

5.0 (8)

from
$126

Grape Stomping Experience and Wine Tasting

Would you like to take a dive into the past? The grape harvest is one of the most important times of the year. Usually it …More

Florence, Italy

4.8 (9)

Grape Stomping Experience and Wine Tasting

Would you like to take a dive into the past? The grape harvest is one of the most important times of the year. Usually it...

2 hours

4.8 (9)

from
$170

From Pisa: Private Volterra, San Gimignano & Wine Lunch

A private day from the Pisa area to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • …More

Pisa, Italy

5.0 (2)

From Pisa: Private Volterra, San Gimignano & Wine Lunch

A private day from the Pisa area to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. •...

8 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$272

From Pisa: Private Florence Day Tour with Chianti Farm Lunch

A full private day from the Pisa area to Florence and the Tuscan countryside, with a genuine farm lunch. • Pick-up at your hotel in …More

Pisa, Italy

5.0 (2)

From Pisa: Private Florence Day Tour with Chianti Farm Lunch

A full private day from the Pisa area to Florence and the Tuscan countryside, with a genuine farm lunch. • Pick-up at your hotel in...

10 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$261

From Florence: Full-Day Chianti & San Gimignano with Farm Lunch

A full day in the heart of Tuscany, with lunch at a real family farm among the vineyards. • Small group, maximum 7 guests, in …More

Florence, Italy

5.0 (2)

From Florence: Full-Day Chianti & San Gimignano with Farm Lunch

A full day in the heart of Tuscany, with lunch at a real family farm among the vineyards. • Small group, maximum 7 guests, in...

6 hours Free Cancellation

5.0 (2)

from
$153

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?