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Top San Gimignano Dining Experiences

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San Gimignano Tours

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Wine and food tasting in an organic family winery

Guided tour of our winery estate near San Gimignano: vegetable garden, orchard, vineyard, olive grove, Vin Santo aging room (vinsantaia), historic cellar, and a collection …More

5.0 (149)

Wine and food tasting in an organic family winery

Guided tour of our winery estate near San Gimignano: vegetable garden, orchard, vineyard, olive grove, Vin Santo aging room (vinsantaia), historic cellar, and a collection...

2 hours 45 minutes • Free Cancellation
5.0 (149)
from
$93
Wine Tour with Lunch and Wine Tasting

It is an authentic experience of a family vineyard where you can understand the wine making process, enjoying the final products. An interesting visit of …More

5.0 (75)

Wine Tour with Lunch and Wine Tasting

It is an authentic experience of a family vineyard where you can understand the wine making process, enjoying the final products. An interesting visit of...

2 hours 30 minutes • Free Cancellation
5.0 (75)
from
$75
Vineyard visit with local appetisers and wine tasting

It is an authentic experience of a family vineyard where you can understand the wine making process, enjoying the final products. An interesting visit of …More

4.9 (14)

Vineyard visit with local appetisers and wine tasting

It is an authentic experience of a family vineyard where you can understand the wine making process, enjoying the final products. An interesting visit of...

1 hour 30 minutes • Free Cancellation
4.9 (14)
from
$60
Food and Wine Lesson and Wine Tasting in San Gimignano

The tasting of the six wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests, …More

5.0 (11)

Food and Wine Lesson and Wine Tasting in San Gimignano

The tasting of the six wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests,...

2 hours • Free Cancellation
5.0 (11)
from
$75
Cesani Wine Experience

The Cesani family and our staff are pleased to welcome you to Pancole, just 5km from the historic center of San Gimignano, where you will …More

Likely to Sell Out
Likely to Sell Out
4.9 (40)

Cesani Wine Experience

The Cesani family and our staff are pleased to welcome you to Pancole, just 5km from the historic center of San Gimignano, where you will...

1 hour 30 minutes • Free Cancellation
4.9 (40)
from
$44
Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

Likely to Sell Out
Likely to Sell Out
4.8 (19)

Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes • Free Cancellation
4.8 (19)
from
$79
Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you …More

Likely to Sell Out
Likely to Sell Out
4.8 (15)

Private Tuscan Lunch with Wine & Evo oil tasting in the Vineyard

This is more than just a lunch—it’s a journey into Tuscan tradition. Unlike standard wine tastings, this experience connects you to the land, teaching you...

1 hour 30 minutes • Free Cancellation
4.8 (15)
from
$110
Truffle Lunch & Hunting Experience in San Gimignano

Join an authentic truffle hunting and experience the thrill of finding, smelling, and touching one of nature’s rarest treasures. Led by expert truffle hunters Mirco …More

4.9 (42)

Truffle Lunch & Hunting Experience in San Gimignano

Join an authentic truffle hunting and experience the thrill of finding, smelling, and touching one of nature’s rarest treasures. Led by expert truffle hunters Mirco...

3 hours • Free Cancellation
4.9 (42)
from
$226
Private wine & EVO Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia …More

Likely to Sell Out
Likely to Sell Out
5.0 (5)

Private wine & EVO Oil Tasting with Tuscan Meal

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia...

1 hour 30 minutes • Free Cancellation
5.0 (5)
from
$79
Tuscan Pasta & Wine Experience in San Gimignano: Cook & Taste

Discover the secrets of Italian pasta-making in this immersive Fresh Pasta Cooking Class in San Gimignano. In a stunning Tuscan winery, you’ll learn how to …More

4.8 (6)

Tuscan Pasta & Wine Experience in San Gimignano: Cook & Taste

Discover the secrets of Italian pasta-making in this immersive Fresh Pasta Cooking Class in San Gimignano. In a stunning Tuscan winery, you’ll learn how to...

3 hours • Free Cancellation
4.8 (6)
from
$219
Authentic Tuscan Cooking Class & Winery Tour in San Gimignano

Your culinary journey begins with an antipasto of three types of bruschetta: - Fettunta, the purest form of bruschetta with garlic and extra virgin olive …More

5.0 (7)

Authentic Tuscan Cooking Class & Winery Tour in San Gimignano

Your culinary journey begins with an antipasto of three types of bruschetta: - Fettunta, the purest form of bruschetta with garlic and extra virgin olive...

3 hours • Free Cancellation
5.0 (7)
from
$184
Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is …More

4.8 (6)

Private Wine & Evo oil tasting with Truffle Meal

✅ Gourmet Truffle Lunch – Savor a multi-course meal featuring the unique and precious flavors of truffles. ✅ Exclusive Wine Pairing – Each dish is...

1 hour 30 minutes • Free Cancellation
4.8 (6)
from
$110
Extra Virgin Olive Oil Experience

Enjoy the extraordinary experience of our extra virgin olive oil tasting; we go along with you in a sensory journey to discover the "liquid gold" …More

Likely to Sell Out
Likely to Sell Out
4.5 (2)

Extra Virgin Olive Oil Experience

Enjoy the extraordinary experience of our extra virgin olive oil tasting; we go along with you in a sensory journey to discover the "liquid gold"...

1 hour • Free Cancellation
4.5 (2)
from
$14
Essence of Tuscany - Private Wine & Evo oil Tasting

✅ Exclusive Wine, Olive Oil Tasting & Balsamic Vinegar tasting – Savor a selection of our organic wines and extra virgin olive oils, straight from …More

4.7 (24)

Essence of Tuscany - Private Wine & Evo oil Tasting

✅ Exclusive Wine, Olive Oil Tasting & Balsamic Vinegar tasting – Savor a selection of our organic wines and extra virgin olive oils, straight from...

1 hour • Free Cancellation
4.7 (24)
from
$58
Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on …More

Likely to Sell Out
Likely to Sell Out
5.0 (2)

Private Wine & Evo Oil Tasting with Saffron Meal

This is more than just a meal—it’s a journey into the heart of Tuscany, celebrating one of San Gimignano’s most treasured ingredients: saffron. Set on...

1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$87
Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal

1) A Unique Perspective on Wine – Beyond just tasting, you'll explore wine’s lesser-known by-product: balsamic vinegar, crafted from grape must. 2) An Exclusive and …More

4.7 (12)

Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal

1) A Unique Perspective on Wine – Beyond just tasting, you'll explore wine’s lesser-known by-product: balsamic vinegar, crafted from grape must. 2) An Exclusive and...

1 hour 30 minutes • Free Cancellation
4.7 (12)
from
$87
5 hour cooking class with traditional food

This Tuscan dining experience is perfect for groups of friends or couples looking to spend quality time together, learning new culinary skills and creating lasting …More

Likely to Sell Out
Likely to Sell Out
5.0 (2)

5 hour cooking class with traditional food

This Tuscan dining experience is perfect for groups of friends or couples looking to spend quality time together, learning new culinary skills and creating lasting...

5 hours • Free Cancellation
5.0 (2)
from
$162
Tuscan Wine & Bruschetta Tasting for Families in San Gimignano

Set in a stunning Tuscan vineyard, this winery tour and tasting offers a perfect mix of authentic flavors, culture, and family-friendly fun. Begin with a …More

5.0 (2)

Tuscan Wine & Bruschetta Tasting for Families in San Gimignano

Set in a stunning Tuscan vineyard, this winery tour and tasting offers a perfect mix of authentic flavors, culture, and family-friendly fun. Begin with a...

2 hours • Free Cancellation
5.0 (2)
from
$45
San Gimignano: Chianti wine tasting

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up …More

5.0 (8)

San Gimignano: Chianti wine tasting

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up...

1 hour • Free Cancellation
5.0 (8)
from
$35
Private Wine, Evo oil & Cheese Tasting

✅ Authentic Tuscan Wine Tasting – Savor 4 to 5 organic wines, including Vernaccia di San Gimignano and Chianti Colli Senesi. ✅ Olive Oil & …More

4.9 (9)

Private Wine, Evo oil & Cheese Tasting

✅ Authentic Tuscan Wine Tasting – Savor 4 to 5 organic wines, including Vernaccia di San Gimignano and Chianti Colli Senesi. ✅ Olive Oil &...

1 hour • Free Cancellation
4.9 (9)
from
$58

Frequently Asked Questions

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

Recent tour reviews
NJ in the house
New York City
Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal
Ellen_K, Sep 2026
NJ in the house
Fun lunchtime activity with a beautiful view! Great picture spot too. The food was delicious and plenty of it.
Read more
Worth
New York City
Truffle Lunch & Hunting Experience in San Gimignano
Ryan_D, Sep 2026
Worth
Lucca the guide is awesome. Learned a ton and he will be someone we would contact if we travel to Tuscany again. The experience with the winery was very nice but the highlight for us was hanging out with Lucca and his dog Lilly
Read more
Relaxed, informative, easy food and great wine!
New York City
Wine Tour with Lunch and Wine Tasting
mikebH3035RO, Sep 2026
Relaxed, informative, easy food and great wine!
Great experience with a tour around the vineyard which was very interesting. This was followed by the wine tasting and lunch which was fantastic and lasted much longer than expected. Very relaxed throughout with no pressure to buy the wine or olive oil.
Read more
Awesome
New York City
Wine Tour with Lunch and Wine Tasting
Experience449303, Sep 2026
Awesome
Wonderful experience and some of the best wines we tasted in tuscany.
Read more
5 Star Tuscan organic wine with unbelievable food and friendly family atmosphere.
New York City
Wine and food tasting in an organic family winery
Aeropete1, Sep 2026
5 Star Tuscan organic wine with unbelievable food and friendly family atmosphere.
Wow! What an amazing experience. The wine is wonderful and the food is fabulous! It’s a small organic family winery and they welcome you in like you are family! Perfect way to spend 3 hours of your Tuscan afternoon! 🍷🤩
Read more
Best thing have done on 21 day trip!
New York City
Wine and food tasting in an organic family winery
Wytana_T, Sep 2026
Best thing have done on 21 day trip!
Fantastic! Best thing we have done on trip so far! Every group has their own table. There were only 4 groups (10 people total) on tour so very intimate. Started with focaccia and first glass of wine then tour of vineyards and cellar. Then back for tastings and food. We had a rain storm come in and it was magical. We were on covered porch (protected from rain) with twinkling lights and great food and wine! Plus no hard sell to buy at end like others we have done in area. Outstanding!
Read more
Perfect afternoon!
New York City
Vineyard visit with local appetisers and wine tasting
Toran65, Sep 2026
Perfect afternoon!
This wine tasting experience was fantastic! The guide was knowledgeable-husband to the owner-and interesting! The wines and food pairings were delicious. It was set in a beautiful backdrop of vineyards. Would highly recommend!
Read more
Delicious food and wine...
New York City
Authentic Tuscan Cooking Class & Winery Tour in San Gimignano
Victoria_S, Sep 2026
Delicious food and wine...
Delicious food and wine and an excellent guide for our experience. She was very friendly and did a great job teaching us about the property and how to make all of the dishes. Would 100% do again!
Read more
Great tasting experience at La Marronaia
New York City
Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal
142MarkS, Sep 2026
Great tasting experience at La Marronaia
Our olive oil, balsamic vinegar & wine tasting with lunch at La Marronaia was absolutely lovely - organised for us by the outstanding PEK Tuscany tour operator as part of a transfer tour between Florence and the Chianti region It's a hugely picturesque spot, the staff are first class and the food delicious. The olive oil and wine were excellent, but the balsamic vinegars (we tried four) were out of this world, I had never tasted anything as good and splashed on two bottles (white & "Oro") to take home!
Read more
Fantastic experience!!!
New York City
Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal
Stay301305, Aug 2026
Fantastic experience!!!
It was a beautiful tasting experience. Our host was knowledgeable and explained the different olive oils, balsamic vinegars and how and when to use them. We had a fantastic afternoon. 5 🌟🌟🌟🌟🌟
Read more
FABULOUS TOTALLY WORTH IT HIGHLY RECOMMEND
New York City
Private Wine, Evo Oils & Balsamic Vinegar Experience with Meal
lguaty, Aug 2026
FABULOUS TOTALLY WORTH IT HIGHLY RECOMMEND
Absolutely amazing experience! Far exceeded my expectations! Lovely surroundings, and wonderful explanation of oliveoils and balsamic vinegars and wines. This place was really breathtaking! And obviously everything was delicious!
Read more
Wine and cellar
New York City
Cesani Wine Experience
jimgC2972LT, Aug 2026
Wine and cellar
Mariluisa and Leticia are the best and the vino is buonissimo. Today marks our 9th visit to Cesani.
Read more
Had an amazing time...
New York City
Authentic Tuscan Cooking Class & Winery Tour in San Gimignano
Nicole_C, Aug 2026
Had an amazing time...
Had an amazing time learning to make pasta with my 2 teenage boys. On the drive up, my 17 year old was complaining (where do you even find this stuff, mom?), but within 30 mins had a huge smile, got a “this is really fun” and “ this makes me want to cook”. I call that a huge win. Highly recommend.
Read more
Great wine! Nice staff!...
New York City
Tuscan Wine & Bruschetta Tasting for Families in San Gimignano
Crystal_D, Jul 2026
Great wine! Nice staff!...
Great wine! Nice staff! No transportation from pickup location. But the staff at winery brought us back to pick up location very kind staff.
Read more
Awesome experience, perfect view
New York City
Private Wine & Evo oil tasting with Truffle Meal
onkelandy66, Jul 2026
Awesome experience, perfect view
So beautiful! Perfect view! Very good food with interesting wine. Nice staff. Also cool with kids.
Read more
Wonderful experience!
New York City
Truffle Lunch & Hunting Experience in San Gimignano
deborah_m, Jul 2026
Wonderful experience!
Truffle hunting with Luca and his beautiful dog Lily was a wonderful experience. I learnt alot about the various types of truffles, how they grow and when the black/white truffles are available. Watching Lily search for truffles was a delight. Lucca presented us with a gift of truffles which was completely unexpected. The truffle lunch and wine tasting at the farm was excellent. The service was amazing and the staff was kind and respectful. This is a must experience for any truffle lover to do when visiting San Gimignano. 10/10
Read more
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