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 →

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
$257

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

Visit to the Bufale and Dairy farm with cheese tasting

Visiting our farm means exploring a historical reality of the Tuscan Maremma, a traditional family farm - which today has been able to transform itself …More

4.6 (12)

Visit to the Bufale and Dairy farm with cheese tasting

Visiting our farm means exploring a historical reality of the Tuscan Maremma, a traditional family farm - which today has been able to transform itself...

1 hour 30 minutes Free Cancellation

4.6 (12)

from
$23

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

Private Vintage Fiat 500 tour in Chianti

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 (2)

Private Vintage Fiat 500 tour in Chianti

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...

6 hours Free Cancellation

5.0 (2)

from
$294

The art of the Italian Aperitivo with a local: Learn & Enjoy in Siena

Your day in Siena is just winding down, the sun's about to set... It's time for an Aperitivo. This glamorous Italian tradition is loved all over the …More

5.0 (2)

The art of the Italian Aperitivo with a local: Learn & Enjoy in Siena

Your day in Siena is just winding down, the sun's about to set... It's time for an Aperitivo. This glamorous Italian tradition is loved all over the...

2 hours Free Cancellation

5.0 (2)

from
$119

Tasting of the Best Wines in Siena in an Etruscan Crypt

Taste the best Tuscan and national wines, accompanied by a selection of tasty local pecorino cheeses in a suggestive Etruscan crypt. My wine shop is …More

5.0 (8)

Tasting of the Best Wines in Siena in an Etruscan Crypt

Taste the best Tuscan and national wines, accompanied by a selection of tasty local pecorino cheeses in a suggestive Etruscan crypt. My wine shop is...

1 hour Free Cancellation

5.0 (8)

from
$143

We will have a tasting of the main labels of the Castello di Bossi, one of the Italian excellence in wine production. What will we …More

5.0 (5)

Complete tasting of Castello di Bossi

We will have a tasting of the main labels of the Castello di Bossi, one of the Italian excellence in wine production. What will we...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$103

Cook Pasta, Wine-Braised Meat & Dessert (Includes 4-Course Meal)

Cook a multi-course Tuscan feast in this 4-course cooking class with wine included, hosted through Cozymeal. Located in Siena, this immersive cooking experience celebrates the …More

5.0 (1)

Cook Pasta, Wine-Braised Meat & Dessert (Includes 4-Course Meal)

Cook a multi-course Tuscan feast in this 4-course cooking class with wine included, hosted through Cozymeal. Located in Siena, this immersive cooking experience celebrates the...

3 hours Free Cancellation

5.0 (1)

from
$188

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors …More

5.0 (4)

Private Ebike Tour in Chianti

Unsurprisingly, Tuscany is one of the favorite destinations for cycling enthusiasts: the views, the scent of the trees along the avenues, and the typical colors...

6 hours Free Cancellation

5.0 (4)

from
$274

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences * …More

5.0 (2)

Suvereto Wine Experience PRIVATE TOUR from SIENA

* An UNIQUE off-the-beaten-path tour. Amazing locations, stunning masterpieces of architecture designed by Renzo Piano and Mario Botta.... * A family-run boutique winery experiences *...

10 hours Hotel pickup offered

5.0 (2)

from
$272

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads, …More

5.0 (2)

Private Off Road Wine Tour in Chianti from Siena

Discover the highlights of Chianti Classico riding through Tuscany’s scenic backroads in a 4WD. There’s a certain magic in traveling along the hidden gravel roads,...

6 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$340

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully …More

5.0 (3)

Brunello di Montalcino wine experience with a sommelier

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully...

5 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$228

Cooking Class at a Farmhouse in Val d'Orcia Tuscany

Small-group Italian cooking class at a breathtaking farmhouse set in the rolling hills of Tuscany! Hands on experience: learn to make home-made Pasta, Tuscan roast …More

5.0 (4)

Cooking Class at a Farmhouse in Val d'Orcia Tuscany

Small-group Italian cooking class at a breathtaking farmhouse set in the rolling hills of Tuscany! Hands on experience: learn to make home-made Pasta, Tuscan roast...

5 hours Free Cancellation

5.0 (4)

from
$195

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October. …More

5.0 (3)

Private Truffle Hunt in Tuscany

Any season has its own truffles, the black you can find almost all year round and the celebrated white ones, which season starts in October....

4 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$241

Cooking Class: Italian Authentic Recipes with Lunch

Want to get your hands dirty with dough? This is the cooking class experience for you! You will learn how to cook simple and delicious …More

4.7 (3)

Cooking Class: Italian Authentic Recipes with Lunch

Want to get your hands dirty with dough? This is the cooking class experience for you! You will learn how to cook simple and delicious...

3 hours Free Cancellation

4.7 (3)

from
$88

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?