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Top Siena Dining Experiences

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Siena Tours

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Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
4.8 (111)

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Enjoy an exclusive wine tasting combined with a typical Tuscan lunch in a medieval Castle in the heart of Montalcino....

1 hour 30 minutes • Free Cancellation
4.8 (111)
from
$70
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
4.9 (338)

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Tuscan Cooking Class. Cooking Class of a traditional Tuscan meal from starter to dessert including a fresh local handmade pasta. At the end of the...

4 hours • Free Cancellation
4.9 (338)
from
$154
Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
4.9 (230)

Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better

Siena is one of Tuscany's best-loved cities, a fixed stop for those in the Chianti region. A destination for many visitors, Siena is internationally known...

3 hours • Free Cancellation
4.9 (230)
from
$86
Classic Wine Tasting with Traditional Tuscan Products
Likely to Sell Out
Likely to Sell Out
4.9 (65)

Classic Wine Tasting with Traditional Tuscan Products

There are places you visit and others you live. A few minutes from Siena, between the Chianti hills and the Crete Senesi, the experience slowly...

1 hour 30 minutes • Free Cancellation
4.9 (65)
from
$33
Tuscany Hiking Tour from Siena Including Wine Tasting
4.9 (121)

Tuscany Hiking Tour from Siena Including Wine Tasting

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of...

4 hours • Free Cancellation
4.9 (121)
from
$71
Wine Class - Tuscan Classics
5.0 (262)

Wine Class - Tuscan Classics

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and...

2 hours • Free Cancellation
5.0 (262)
from
$71
Cooking Class in a historical Palace in Siena Provence
4.9 (42)

Cooking Class in a historical Palace in Siena Provence

• Warm Welcome & Tasting – Begin your experience with freshly brewed coffee and an extra virgin olive oil tasting, where you’ll uncover the secrets...

3 hours • Free Cancellation
4.9 (42)
from
$138
Montalcino: Brunello Wine Tasting Experience
4.5 (56)

Montalcino: Brunello Wine Tasting Experience

Enjoy 1.5 hour wine tasting experience in an elegant medieval Castle in the heart of Montalcino. Together with an expert sommelier, don't miss the chance...

1 hour 30 minutes • Free Cancellation
4.5 (56)
from
$38
Tuscan, Italian, tiramisu cooking class and tasting 3 wines
4.8 (28)

Tuscan, Italian, tiramisu cooking class and tasting 3 wines

The academy is much more than a cooking school where you can learn traditional dishes, it is an authentic experience that blends tradition, local flavors...

3 hours • Free Cancellation
4.8 (28)
from
$100
Cook and Taste with a Local in Siena by Cesarine
5.0 (33)

Cook and Taste with a Local in Siena by Cesarine

Immerse yourself in a small group cooking class at local's home,  learn the secrets of the most famous dishes of Siena cuisine and taste the fruit of...

3 hours • Free Cancellation
5.0 (33)
from
$200
Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the
4.8 (35)

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
4.8 (35)
from
$59
Savor Siena Food and Wine Tour
4.9 (38)

Savor Siena Food and Wine Tour

Savor Siena offers a chance to not only taste, but to learn about Tuscany’s wealth of foods, with a particular focus on what's Sienese. See...

2 hours • Free Cancellation
4.9 (38)
from
$71
Cesarine: Small group Pasta and Tiramisu class in Siena
4.9 (22)

Cesarine: Small group Pasta and Tiramisu class in Siena

You can't visit Italy without trying at least one pasta dish... So, we'll teach you two! Learn how to roll 'sfoglia' (fresh pasta) by hand...

3 hours • Free Cancellation
4.9 (22)
from
$212
Truffle Hunting Experience Siena Tartufi
Likely to Sell Out
Likely to Sell Out
5.0 (56)

Truffle Hunting Experience Siena Tartufi

Ciao, I’m Alessandro, the owner of Siena Tartufi. I’m a truffle hunter from 25 years. I have 3 dogs, Moka and Freddie a Lagotto Romagnolo...

2 hours • Free Cancellation
5.0 (56)
from
$166
Explore Siena Market & Cook at a Local’s Home by Cesarine
Likely to Sell Out
Likely to Sell Out
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
$212
Cesarine: Typical Dining & Cooking Demo at Local's Home in Siena
5.0 (22)

Cesarine: Typical Dining & Cooking Demo at Local's Home in Siena

Immerse yourself in a dining experience at a local's home, enjoy an exclusive show cooking and taste authentic Siena recipes treasured in family cookbooks passed down by real...

2 hours 30 minutes • Free Cancellation
5.0 (22)
from
$153
2 Hours Visit and Wine Tasting with tastings in Val D'Orcia
5.0 (56)

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 (56)
from
$83
Montalcino: Brunello Wine Tasting & Tuscan Lunch
5.0 (10)

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
5.0 (10)
from
$116
Cesarine: Pasta & Tiramisu Class at a Local's Home in Siena
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
$223
Discover Brunello Wines
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
$291

Frequently Asked Questions

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

Recent tour reviews
Worth the money
New York City
Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
davidpL5488PK, Sep 2026
Worth the money
We really enjoyed the culture and the history and the food was amazing
Read more
Good mix of good food and...
New York City
Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
John_D, Sep 2026
Good mix of good food and...
Good mix of good food and knowledge presented of Siena from the guide. It was about 3 hours and was very walkable.
Read more
Wonderful Tuscan Lunch
New York City
Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
Joseph_S, Sep 2026
Wonderful Tuscan Lunch
This was an amazing experience. Way more than I had expected. We started with a tour of the property, lead by a very knowledgeable young lady (name escapes me). This was followed by a tasting experience of 4 of their wines (2 Brunellos), paired with a very nice lunch, antipasto and a wonderful, home made pasta.Of course, the best part was getting to meet so many fellow travelers during the lunch. It started down pouring as we headed back out to the car, so we all stayed inside for a while longer. There was no feeling of being rushed out of there because “our time was up”.This trip far exceeded expectations and was a great value at the offered price. This is a trip I will do again the next time I come back to the area.
Read more
Hands on interactive cookery course
New York City
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
oliveCapeTown, Sep 2026
Hands on interactive cookery course
We were a group of 9. Such a fun experience and can honestly say the best meal we have had in Italy.
Read more
Amazing and Memorable Culinary Experience
New York City
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
dqgreenwood, Sep 2026
Amazing and Memorable Culinary Experience
Amazing experience!!! My wife and I loved the class where Chef Francesco taught us how to cook four separate courses in the Tuscany tradition. Francesco and Julia made the entire experience memorable. The four dishes included antipasta which was La Pappa Col Pomodoro; homemade pici pasta; Tagliata Steak with caramelized onions; and Cantuccini Biscotti. With each dish they explained the background, local ingredients and tradition, and then coached us to prepare ourselves. Their personalities and knowledge were the perfect combination to make the experience incredibly enjoyable and beyond worthwhile. Best of all, you get the experience and the recipes to take home to try for yourself. If you want the quintessential Siena/Tuscan experience, don’t miss Chef Francesco, Julia, and their classes. It will be the highlight of your visit!
Read more
Best winery ever!
New York City
2 Hours Visit and Wine Tasting with tastings in Val D’Orcia
janajford, Sep 2026
Best winery ever!
Tatiana is wonderful! She is so interesting and fun! It is the most beautiful winery! The wine is so clean and delicious! We highly recommend! Thank you Tatiana! We will see you again! Jana and Joe
Read more
Awesome wine and lunch!
New York City
Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
gne4thewkend, Sep 2026
Awesome wine and lunch!
The guide made it very interesting and the three course lunch and wine tasting was awesome!! Definitely recommend!
Read more
Absolutely loved the...
New York City
Tuscan, Italian, tiramisu cooking class and tasting 3 wines
Suska_T, Sep 2026
Absolutely loved the...
Absolutely loved the class! Simona was a fantastic and knowledgeable teacher (and her English was perfecto). She brought strangers together and we had so much fun making tiramisu and 3 pastas, which we all delighted in eating afterwards over wine! Would highly recommend to anyone.
Read more
A fantastic cookery course
New York City
Tuscan, Italian, tiramisu cooking class and tasting 3 wines
G4536UElouiser, Aug 2026
A fantastic cookery course
An excellent experience. Our chef was so friendly and patient . We made 3 pastas and a tiramisu and then enjoyed eating them with Prosecco and 3 red wines. A really memorable & fun day !
Read more
Fun experience in a castle
New York City
Montalcino: Brunello Wine Tasting Experience
L3260GIbethm, Aug 2026
Fun experience in a castle
This wine tasting was a lot of fun; our guide gave us the history of the castle and showed us the wine cellar and discussed the specialties of the winery. We had a lovely tasting of several wines. There were only 4 of us total so that made it nice and intimate. Wine was excellent. Would recommend.
Read more
Excellent experience!
New York City
Montalcino: Brunello Wine Tasting & Tuscan Lunch
Zornitsa_R, Aug 2026
Excellent experience!
Excellent experience! Top quality wines! Delicious homemake food! 1.5 hours of interesting information, wine testing and great environment! Highly recommended!
Read more
Very good! Service from the restaurant is very pleasant
New York City
Chianti Grand Tasting: Signature Wines, Oils & Balsamics in the
marialeticiaw2026, Jul 2026
Very good! Service from the restaurant is very pleasant
What an amazing experience! Wonderful service and wonderful food.
Read more
Magical experience
New York City
2 Hours Visit and Wine Tasting with tastings in Val D’Orcia
901migles, Jul 2026
Magical experience
This was our very first wine tasting experience, and thanks to Poggio del Moro, it became truly magical! The owner's warm and welcoming hospitality, the wealth of fascinating information, the open and engaging atmosphere that encouraged questions, and the exceptionally charming tasting room—where we felt as if we were in a castle—all made the experience unforgettable. I arrived convinced that I only liked white wine, but here I discovered a love for red wine as well. It turns out all I needed was a professional introduction to the wonderful world of wine. Thank you for creating memories that we will carry in our hearts for a long time to come! ❤️
Read more
Worth recommending
New York City
Montalcino: Brunello Wine Tasting Experience
leopoldinek2026, Jul 2026
Worth recommending
Very personal guidance, competent, open to questions. Time for the tasting.
Read more
Truffles Before the Palio: Guided by Alessandro, Led by Mocha
New York City
Truffle Hunting Experience Siena Tartufi
Cristina_G, Jul 2026
Truffles Before the Palio: Guided by Alessandro, Led by Mocha
A perfect morning with Mocha (the true star of the show) and Alessandro (the trainer, guide, and heart of the experience). Two words come to mind: ”professionalism” and ”efficiency”. But that hardly tells the story. What we actually found was genuine fun, captivating insights, and plenty of useful information. The reward? Twenty truffles unearthed in just 30–40 minutes — some of them the size of a good potato! And then came the truly ”Sienese” finale. Alessandro's charming little shop, nestled right on Piazza del Campo, was the perfect place to end the morning. With the city alive with the extraordinary atmosphere of the Palio, tasting Tuscan specialties and freshly harvested truffles offered by Alessandro, surrounded by the passionate supporters of the Contrade was an experience we will not forget. Thank you, Alessandro. And above all, thank you, Mocha!
Read more
This was the best...
New York City
Cook and Taste with a Local in Siena by Cesarine
Jackie_C, Jun 2026
This was the best...
This was the best experience of our trip. We attended with 3 adults and 4 kids (ages 10-6) and could not recommend this enough! The girls were engaged and had time to both enjoy, learn, and soak in all of the beautiful family's culture. We loved Fabio and Antonella! They felt like family.
Read more
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