Top Siena Food, Wine & Nightlife

Q: Which Siena Food, Wine & Nightlife have Instant Confirmation?

Siena Food, Wine & Nightlife with Instant Confirmation include: Siena: Val d’Orcia Wine Tour with Lunch & Brunello A Brunello Cooking Class with Vineyards View Winery Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner Siena: A Wine Tour and Tasting Experience Small-Group Tuscan Cooking Class with Wine & Lunch from Siena View all Tours with Instant Confirmation →

Q: I need a ride! Which Siena Food, Wine & Nightlife have Hotel Pickup?

No problem. These Siena Food, Wine & Nightlife 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 Cooking Class in Chianti from Siena Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour 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 →

Explore Siena Market & Cook at a Local’s Home by Cesarine

Visit the vibrant local market and the traditional food shops with the Cesarina and immerse yourself in a cooking class at the Cesarina's home, learn the secrets of the …More

5.0 (5)

Explore Siena Market & Cook at a Local’s Home by Cesarine

Visit the vibrant local market and the traditional food shops with the Cesarina and immerse yourself in a cooking class at the Cesarina's home, learn the secrets of the...

4 hours 30 minutes Free Cancellation

5.0 (5)

from
$203

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
$135

Private Cooking Class in Chianti from Siena

Culinary tradition is a protagonist of Tuscan culture, and a major part of the experience visiting the region. We will be hosted in an organic …More

5.0 (10)

Private Cooking Class in Chianti from Siena

Culinary tradition is a protagonist of Tuscan culture, and a major part of the experience visiting the region. We will be hosted in an organic...

5 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$268

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
$795

Cesarine: Pasta & Tiramisu Class at a Local's Home in Siena

Immerse yourself in a private pasta and tiramisu-making class in a welcoming home, learn the secrets of the region's most famous pasta dishes and tiramisu and taste …More

4.8 (18)

Cesarine: Pasta & Tiramisu Class at a Local's Home in Siena

Immerse yourself in a private pasta and tiramisu-making class in a welcoming home, learn the secrets of the region's most famous pasta dishes and tiramisu and taste...

3 hours Free Cancellation

4.8 (18)

from
$215

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

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked …More

5.0 (11)

The Most Delicious Private Food Tour of Siena: 10 Tastings

Fall in love with the flavorful Tuscan cuisine on this private food tour in Siena! Enjoy a selection of 10 food and drink tastings hand-picked...

3 hours Free Cancellation

5.0 (11)

from
$110

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

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

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

Siena Small group Cooking Class in a Chianti Farm

Your cooking class is based on a traditional Tuscan Chianti Farmhouse with an expert Italian chef which has ma y years of experience. It is …More

5.0 (21)

Siena Small group Cooking Class in a Chianti Farm

Your cooking class is based on a traditional Tuscan Chianti Farmhouse with an expert Italian chef which has ma y years of experience. It is...

3 hours 30 minutes Free Cancellation

5.0 (21)

from
$114

Dive into Siena like a local foodie. Explore your Cesarina's most trusted artisanal food shops, tasting as you go. Visit a selection of small local …More

5.0 (2)

Small-group Street food tour in Siena

Dive into Siena like a local foodie. Explore your Cesarina's most trusted artisanal food shops, tasting as you go. Visit a selection of small local...

3 hours Free Cancellation

5.0 (2)

from
$101

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

Siena walking tour with Gelato & Prosecco

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is …More

4.9 (9)

Siena walking tour with Gelato & Prosecco

This is a city walking tour that will give you the occasion the see this city from the eyes of a local. Your Guide is...

1 hour 30 minutes Free Cancellation

4.9 (9)

from
$62

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello …More

5.0 (3)

From Siena: Private Brunello & Nobile Wine Tour with Lunch

A private wine day from Siena to the Val d'Orcia, home of two of the greatest Italian red wines: Vino Nobile di Montepulciano and Brunello...

9 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$261

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

From Siena: Private Volterra, San Gimignano & Wine Lunch

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)

From Siena: Private Volterra, San Gimignano & Wine Lunch

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

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

Frequently Asked Questions

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

What are the best options for Siena Food, Wine & Nightlife?

What are the best kid-friendly options for Siena Food, Wine & Nightlife Tours?

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

View all kid-friendly Tours →

Which Siena Food, Wine & Nightlife have Instant Confirmation?

Which Siena Food, Wine & Nightlife have Free Cancellation?

Siena Food, Wine & Nightlife 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 Food, Wine & Nightlife have Hotel Pickup?

Got any more Siena trip ideas?

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