Top Siena Wine Tasting & Winery Tours

Q: Which Siena Wine Tasting & Winery Tours have Instant Confirmation?

Siena Wine Tasting & Winery Tours with Instant Confirmation include: Siena: Val d’Orcia Wine Tour with Lunch & Brunello A Brunello Cooking Class with Vineyards View Winery Siena: A Wine Tour and Tasting Experience Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle Classic Wine Tasting with Traditional Tuscan Products View all Tours with Instant Confirmation →

Q: I need a ride! Which Siena Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Siena Wine Tasting & Winery Tours include Hotel Pickup: Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch Private Tour: Montalcino Wine Tasting Experience Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour Private wine tour of Chianti View all Tours with Hotel Pickup →

Q: Got any more Siena trip ideas?

We sure do. Check out our curated lists of hand-picked Siena Tours. Top 10 Siena 2026 Senior-friendly tours Siena The best tours and activities for culture lovers in Siena Top Day Trips from Siena Things to do in Siena this summer View all Siena Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Siena?

Based on our sales data over the past year, the most popular styles of tours and activities in Siena are: Siena Cultural & Theme Tours Siena Historical & Heritage Tours Siena Luxury & Special Occasions Siena Luxury Tours Siena Walking & Biking Tours View all tour styles in Siena →

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

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

Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring …More

4.7 (36)

Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring...

1 hour 30 minutes Free Cancellation

4.7 (36)

from
$57

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

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

Montalcino: Brunello Wine Tasting & Tuscan Lunch

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, …More

4.9 (14)

Montalcino: Brunello Wine Tasting & Tuscan Lunch

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci,...

1 hour 30 minutes Free Cancellation

4.9 (14)

from
$112

Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run, …More

4.9 (77)

Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

To fully experience la "Bella vita", you need to get out of the city. Taste the local wines & tour the cellars of select family-run,...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (77)

from
$284

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this …More

5.0 (71)

Private Tour: Montalcino Wine Tasting Experience

Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this...

8 hours Hotel pickup offered Free Cancellation

5.0 (71)

from
$308

Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in …More

4.3 (57)

Signature Brunello di Montalcino Wine Tour from Siena

Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in...

5 hours 30 minutes Free Cancellation

4.3 (57)

from
$136

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive …More

5.0 (41)

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive...

8 hours Hotel pickup offered Free Cancellation

5.0 (41)

from
$799

2 Hours Visit and Wine Tasting with tastings in 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

5.0 (58)

2 Hours Visit and Wine Tasting with tastings in 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...

2 hours Free Cancellation

5.0 (58)

from
$80

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will …More

4.6 (10)

Private wine tour of Chianti

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will...

6 to 8 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$325

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

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

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

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

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

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

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

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

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

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

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti. …More

5.0 (3)

Wine & Cheese Experience

The Experience includes: ️ Historic Estate Tour Explore our 1810 wine cellar and the ancient olive mill, while learning about the rich history of Chianti....

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$68

A licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best of …More

5.0 (28)

Discover Brunello Wines

A licensed sommelier, will always be by your side as your driver and guide to share his knowledge and help you discover the best of...

8 hours

5.0 (28)

from
$281

Wine Tour & Tasting - Organic Chianti & Supertuscan

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. - …More

5.0 (1)

Wine Tour & Tasting - Organic Chianti & Supertuscan

Highlights - Historic Estate Tour: Guided 90-minute visit of Montechiaro Villa (since 1760), including the original wine cellar, aging rooms, and ancient olive mill. -...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$51

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

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

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Siena Wine Tasting & Winery Tours?

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

What are the best kid-friendly options for Siena Wine Tasting & Winery Tours Tours?

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

View all kid-friendly Tours →

Which Siena Wine Tasting & Winery Tours have Instant Confirmation?

Which Siena Wine Tasting & Winery Tours have Free Cancellation?

Siena 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 Siena Wine Tasting & Winery Tours have Hotel Pickup?

Got any more Siena trip ideas?

What are the most popular styles of Tours and Activities in Siena?