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 →

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

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

MONTECHIARO Chianti & Supertuscan WINE EXPERIENCE

- Immerse yourself in the world of Tuscan wine with our comprehensive tasting experience. - Master the art of tasting: Learn professional wine and extra …More

5.0 (2)

MONTECHIARO Chianti & Supertuscan WINE EXPERIENCE

- Immerse yourself in the world of Tuscan wine with our comprehensive tasting experience. - Master the art of tasting: Learn professional wine and extra...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$40

Montalcino: Brunello Wine Tasting & Tuscan Dinner

What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the …More

4.8 (5)

Montalcino: Brunello Wine Tasting & Tuscan Dinner

What makes this experience truly unique is the opportunity to enjoy an authentic Tuscan dinner among the vineyards of Paradiso di Cacuci, surrounded by the...

3 hours Free Cancellation

4.8 (5)

from
$188

Nestled in the Chianti hills, visit the estate, whose villa is the historical testimony of a history dating back to the year 1000, and taste …More

3.8 (25)

Chianti Classico wine Tour and Tasting

Nestled in the Chianti hills, visit the estate, whose villa is the historical testimony of a history dating back to the year 1000, and taste...

1 hour 30 minutes Free Cancellation

3.8 (25)

from
$67

Chianti Wines and San Gimignano Tour from Florence (1 Winery)

This is a great opportunity to spend HALF DAY (5 hours) in Tuscany enjoying a great lunch and wine tastings. We will pick you up …More

5.0 (13)

Chianti Wines and San Gimignano Tour from Florence (1 Winery)

This is a great opportunity to spend HALF DAY (5 hours) in Tuscany enjoying a great lunch and wine tastings. We will pick you up...

5 hours Free Cancellation

5.0 (13)

from
$999

PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location …More

5.0 (3)

PRIVATE TOUR: Savor Exquisite Wines: Brunello & Nobile Wine Tour

A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$207

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a …More

5.0 (11)

Wine Tuk Tour Siena

Discover the Chianti Classico wines from an eTuk, from which you can enjoy the a drive through the vineyard covered hills around Siena to a...

3 hours

5.0 (11)

from
$149

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan …More

5.0 (10)

Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE

* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan...

8 hours Hotel pickup offered

5.0 (10)

from
$227

PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at …More

5.0 (4)

PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience

A private day from Siena to two of the most beautiful hill towns of Tuscany, with a genuine farm lunch in between. • Pick-up at...

8 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$272

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

5.0 (17)

Discover Chianti Classico Wines

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

8 hours

5.0 (17)

from
$281

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally …More

4.9 (11)

Private Grape stomping at Chianti Farmhouse

Harvest has always been seen as a time of celebration in the countryside: after months of hard work and sacrifices, all those efforts are finally...

4 hours Free Cancellation

4.9 (11)

from
$251

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines …More

5.0 (19)

Chianti Classico E-Bike Tour

One day bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines...

5 to 6 hours Free Cancellation

5.0 (19)

from
$240

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short …More

5.0 (14)

Siena and San Gimignano, The Glory Of Medieval Age In Tuscany

If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will take you with a short...

8 to 9 hours Free Cancellation

5.0 (14)

from
$122

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation …More

4.1 (15)

The Countess’s Lunch: Wine Tasting Paired with Signature Cuisine

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation...

1 hour 45 minutes Free Cancellation

4.1 (15)

from
$79

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a …More

4.8 (9)

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a...

11 hours Free Cancellation

4.8 (9)

from
$159

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their …More

5.0 (5)

Private Truffle Hunting in Chianti

The Tuscan hills hide real treasures, and we will guide you on an unforgettable tour through the Chianti woods. Discover the secrets of truffles, their...

5 hours Free Cancellation

5.0 (5)

from
$259

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia …More

5.0 (9)

Wine Tasting ATV tour in Tuscan countryside

ATV Excursion in the hearth of Tuscany, in province of Siena, in Crete Senesi UNESCO heritage, between Chianti and Val d'Orcia...

4 hours Free Cancellation

5.0 (9)

from
$365

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in …More

4.7 (19)

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in...

7 hours 15 minutes Free Cancellation

4.7 (19)

from
$179

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

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

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s …More

5.0 (1)

Private Vintage Fiat 500 tour in Chianti From Siena

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$320

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?

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?