Tours/San Gimignano/Castles & Chianti Wine Experience– Small Group from San Gimignano
Viator · group up to 30 pax

Castles & Chianti Wine Experience– Small Group from San Gimignano

4.1(22)San Gimignano1 hour
VIATOR3.9(14)TRIPADVISOR4.5(8)

Description

Experience the beauty of the Chianti region and immerse yourself in the unforgettable Tuscan countryside. Discover the world-famous Chianti wine, known for its ruby-red color and delicate violet aromas, while visiting two wineries in the heart of the Chianti Classico area. Enjoy guided wine tastings paired with typical Tuscan food and extra virgin olive oil, surrounded by stunning vineyard landscapes. The tour begins and ends in the charming medieval town of San Gimignano. Travel comfortably in an air-conditioned minivan for up to 8 people or a minibus for groups of up to 30 people. Note:Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited

Tour Options

Winter tour
  • 12:00PM: Starting time is different during winter season
Summer tour
  • 1:00PM: Starting time during summer season

Itinerary

Admission included60 min

Enjoy a delightful wine tasting experience paired with an informative winery visit.

60 min

Castellina in Chianti is a charming village located in the heart of Tuscany, known for its rich history, picturesque landscapes, and local cuisine. Travellers can explore its historic landmarks, savor local delicacies, and bask in the warmth of its welcoming atmosphere.

40 min

Visit the ancient village of Monteriggioni and take some unforgettable pictures.

Admission included60 min

Enjoy a second wine tasting and visit to a Tuscan winery.

Highlights

Travel in air-conditioned minivan for up to 8 people or minibus for up to 20 people
WiFi on board
travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
Olive oil and balsamic vinegar sampling
Expert multilingual guides
Local products tasting (bread, salami)
Tasting of 7 types of wines in total
Tour of 2 wine estates, one of which is exclusive + 2 wine tastings

What's included

Included
Travel in air-conditioned minivan for up to 8 people or minibus for up to 20 people
WiFi on board
travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
Olive oil and balsamic vinegar sampling
Expert multilingual guides
Local products tasting (bread, salami)
Tasting of 7 types of wines in total
Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
Not included
Gratuities

Pickup Locations & Times

Please note that this service is on request and has an extra cost of 20 euros. The hotel must be more than 10 km from the center of San Gimignano.

Traveller Ratings

4.1
22 reviews
5
15
4
1
3
2
2
2
1
2

Important Information

  • Suitable for all physical fitness levels

Reviews(22)

D
David_B
June 14, 2026
Good driver and guide....

Good driver and guide. Visit to 2 vinyards, tasting good wines. Educational as well as entertaining. Nice visit to Castellina in Chianti and Monteriggione

A
anastasia_b
April 29, 2026
This was the perfect day...

This was the perfect day trip from San Gimignano!! The meeting place was a hard to find, so I would suggest messaging them the morning of to ask for the exact location of the driver because Google Maps doesn’t bring you to the correct place. The driver and tour guide were awesome! It was great to explore a few different towns in Tuscany & taste some great wine, olive oil, and balsamic vinegar at local vineyards!!

Operator response

Dear Customer, Thank you for your feedback! We are delighted to hear that you had a great experience and that Julia, Alessia, and Michel made your excursion enjoyable. We are also happy that you appreciated the organization and the overall experience. Best regards, my Tour in italy

J
jockphil67
September 12, 2025
Very enjoyable tour

It was a great group and a pretty busy afternoon. Val and Antonio were great and made the afternoon memorable. The wineries had ample tastings and good quality wines.

Operator response

Dear Customer, Thank you for sharing your feedback with us! It’s wonderful to know you enjoyed the wineries, the tastings, and the quality of the wines. We hope to welcome you again on another tour soon! Best regards, My Tour In Italy.

O
Olivia_S
July 6, 2025
Unreliable shambles

Waited an hour at the pick-up point in 35 degree heat with no shade, feeling less and less like drinking any wine. Finally decided that they weren’t going to turn up (we weren’t given a contact number, only a chat option to request an email). Returned to accommodation. At that point they phoned- 45 minutes after the supposed start time- to ask where we were. No explanation, no apology, appeared to be slightly bewildered that we were unimpressed.

Operator response

Dear Customer, Thank you for sharing your feedback with us! We’re truly sorry for the long wait in the heat and the lack of communication during that time. We understand how frustrating it must have been, and we deeply regret that we didn’t meet your expectations. Your feedback is important, and we are reviewing our processes to ensure better communication and punctuality in the future. We sincerely apologize for the inconvenience and hope to have the chance to provide a much smoother experience next time. Best regards, My Tour In Italy.

N
Nicole_A
June 2, 2025
MUST READ if leaving from San Gimignano

First off: the tour, wineries, driver and guide were really good & we recommended this tour. There are things we wish we knew/expected when leaving from San Gimignano: - Pick up spot wasn't correct & shuttle had no signs identifing it. We had to walk across the street from meeting point and ask a random Grey shuttle if that was our tour. It was. - You drive 45 minutes to Siena to pick up the tour guide and more people for the tour. This means a 45 minute drive back after the tour from Siena to San Gimignano. - We waited 15-20 minutes once we got to Siena for missing people that couldn't seem to find the meeting point there either. - No food or drink on the shuttle, but you could buy a bottle of water on the shuttle for 1 euro (don't charge for water, just include it). - It wasn't laid out where we were going each time and started the tour with a quick stop in a small town, then back to back wineries, followed up with a castle tour. - started at 1pm, got back to San Gimignano about 8pm We had the whole day and weren't worried time and enjoyed the tour. The 2 wineries were great and very different. The town and castle stops were good too. Just know if leaving from San Gimignano it is a lot of driving time. The shuttle was new and nice. We recommend this tour but this is the information we wished we had.

Operator response

Dear Customer, Thank you for sharing your feedback with us! We’re happy to hear you enjoyed the wineries and visits to the towns and castle. We appreciate your honest comments about the pick-up points, waiting times, and shuttle service. Your insights are very helpful, and we will share them with our team to improve the experience for future guests. Thanks again for sharing your thoughts. We hope to welcome you back soon! Best regards, My Tour in Italy.

R
Ronica_V
May 21, 2025
Tuscany wine tour

This was a fun tour with great wine tasting and views. I don't think the description is completely accurate as far as the stops go. But overall it was great!

Operator response

Dear Customer, Thank you for sharing your feedback with us! We’re glad to hear you enjoyed the tour, the wine tasting, and the beautiful views.We appreciate your note regarding the tour description and stopsyour feedback helps us improve and ensure our descriptions are as accurate as possible. We're happy you had a great time overall, and we hope to welcome you on another tour in the future! Best regards, My Tour In Italy.

P
Peggy_L
October 18, 2023
Great day in Chianti!

The overall tour was very enjoyable. Vincenzo stopped at great places for us to take pictures. We had two wine tastings at beautiful wineries. Stopped in two little towns to walk around. Tour met my expectations.

Operator response

Dear Customer, Thank you for sharing your feedback and letting us know about your experience. We are very glad that you enjoyed the tour and had a good time at each destination. Our customers are our priority, and we always do our best to improve them the best service. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.

V
valdirferreirar
October 18, 2023
Feeling deceived

Lack of information and support over the phone, when selling the tour they answer the phone and when the tourist needs it, they don't answer the phone.😡

Operator response

Dear Customer, Thank you for taking your time and sharing the feedback of your experience with us. We are sorry to know that you were unsatisfied from this tour. Our staff is always at the customers' disposal, and we are sorry to hear this opinion for our staff. We have tried many times to contact you by phone, but we couldn't reach you out. Maybe you had a bad line at the moment we were calling you. The call operators have been ready to answer your calls and assist you in any case of help. For any further issues or concerns regarding the tour, please feel free to contact us at our email address customercare@mytours.it Best regards, My Tour in Italy team.

T
Tom_M
October 18, 2023
A Perfect Day

Had a wonderful day on this wine and castle tour. Vince was an exceptional tour guide, going well beyond the call of duty. He was both informative and innovative in his approach to bringing Tuscany and its vibrant history to life. Highly recommended this tour.

Operator response

Dear Customer, Thank you for sharing your feedback and letting us know about your experience. We are very glad that you enjoyed the tour and had a good time at each destination. Our customers are our priority, and we always do our best to improve them the best service. Thank you for all those good words and for appreciating for our guide's work. Appreciate your recommending this tour to other customers, too. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.

V
VGPM
October 18, 2023
Great Guide Great Tour

Great tour that takes you to two wineries and the walled city of Monteriggioni. The guide was very accommodating( his English was great) and the scenery was great. We had 8 so it was a full tour. You get about an hour in Monteriggioni so plan accordingly. The wall walk only cost 7e (2 senior discount) and does not take much time. Lunch is served in all sorts of cafes from garden view to plaza view so decide which you want before going as you have only 1 hour. Town is very small but well worth the visit. The wineries were very scenic and the tastings were great(also some cheese and meats). 6 hour tour is time well spent. Tour drops you off at the gates in San Gimignanio. You may want to make dinner reservations for after the tour depending on what you do for lunch. The guide was very flexible about the drop off spot( with in reason)

Operator response

Dear Customer, Thank you for sharing your feedback with us. Glad to know that you liked the tour and enjoyed every part of it. Thank you for the good words for our guide and for all your explanation about this tour's itinerary. Wineries are the result of our searching for the best place for our customers to enjoy the time there. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.

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