Tours/San Gimignano/Castles & Chianti Wine Experience– Small Group from San Gimignano
Castles & Chianti Wine Experience– Small Group from San Gimignano
4.0(23)San Gimignano7 hours
VIATOR3.8(15)TRIPADVISOR4.5(8)
+15 photos
At a glance
Duration
7 hours
Price from
$97 / person
Location
San Gimignano, Italy
Rating
4.0 / 5 · 23 reviews
Languages
EN, IT, ES
Group
Small group, up to 30
Cancellation
Free cancellation up to 24 hours before
Confirmation
Instant
Ticket
Mobile or paper ticket accepted
Operator
myTour in Italy
Meeting point
Piazzale Montemaggio San Gimignano, at the bus stop next to the parking lot
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
Schedule & prices
Runs
Tue, Thu, and Sat
Start times
12:00 PM and 1:00 PM
Next available
Tue, Oct 13
Adult (ages 13+)
$97
Child (ages 3–12)
$49
Infant (ages 0–2)
Free
From the operator’s live schedule on Viator, checked Oct 10.
Tour Options
Winter tour
12:00PM: Starting time is different during winter season
Summer tour
1:00PM: Starting time during summer season
Itinerary
Fattoria Lornano
Admission included60 min
Enjoy a delightful wine tasting experience paired with an informative winery visit.
Castellina In Chianti
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.
Monteriggioni
40 min
Visit the ancient village of Monteriggioni and take some unforgettable pictures.
Strada Statale 222 Chiantigiana
Admission included60 min
Enjoy a second wine tasting and visit to a Tuscan winery.
What's included
Included
WiFi on board
Olive oil and balsamic vinegar sampling
Expert multilingual guides
Local products tasting (bread, salami)
Tasting of 7 types of wines in total
Travel in air-conditioned minivan for up to 8 people or minibus for up to 30 people
Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
Not included
Gratuities
Traveller Ratings
Reviews collected by Viator and Tripadvisor
4.0
23 reviews
5
15
4
1
3
2
2
3
1
2
How it compares in San Gimignano
No. 18 by number of reviews among 145 tours in San Gimignano
Excurgo comparison of 145 Viator tours, recalculated daily.
Important Information
Suitable for all physical fitness levels
Please note: The tour includes a brief stop in Siena to pick up additional participants before continuing to the wineries. No visit to Siena is included.
Please note that the Italian option requires a minimum of 4 participants. In case the minimum is not reached, the tour is guaranteed to be in English.
Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
1+ days before100% refund
0–1 days before0% refund
Frequently asked questions
How long does this tour take?
Castles & Chianti Wine Experience– Small Group from San Gimignano lasts about 7 hours. The itinerary has 4 stops.
How much does this tour cost?
Prices start at $97 per person for this San Gimignano experience, booked through Viator with the price shown before checkout. There are 2 booking options, so the final price depends on the option you choose.
What days does this tour run?
According to the operator’s current schedule, it runs on Tuesdays, Thursdays, and Saturdays, starting at 12:00 PM and 1:00 PM.
How much does this tour cost for children?
Children aged 3–12 pay from $49, adults from $97. Infants go free.
Can I cancel this tour for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is Piazzale Montemaggio San Gimignano, at the bus stop next to the parking lot. Hotel pickup is not part of this experience.
What languages is this tour offered in?
The experience is available in EN, IT, ES.
Is this a private or a group tour?
It is a small-group experience with a maximum of 30 participants.
Will my booking be confirmed immediately?
Yes, bookings are confirmed instantly.
Is this tour worth it?
Travellers rate it 4.0 out of 5 across 23 reviews on Viator and Tripadvisor; it is run by myTour in Italy.
Reviews(23)
Reviews collected by Viator and Tripadvisor
M
Melina_G
September 27, 2026 · via Viator
Did not meet the expectations
Unfortunately, this tour did not meet the expectations set by the advertisement.
The tour was advertised as having a maximum of 8 people, but there were around 30 people in our group. The tour was also called “Chianti and Castles,” but we did not visit any castles at all. Instead, we visited two wine producers, where the experience and tastings were quite basic.
The bus was also very difficult to find at the meeting point and arrived late, which made the start of the tour stressful and confusing.
Finally, I specifically booked the tour in Italian, but the tour was conducted in English.
The tour was not accurately represented in the advertisement, particularly regarding the group size, the castles, and the language. I would recommend updating the description so that customers know exactly what to expect.
Operator response
Dear Customer,
Thank you for your feedback!
We are truly sorry to hear that the tour did not fully meet your expectations.
Please note that the group size depends on the number of participants booked for the tour. Regarding the meeting point, all the necessary information is clearly provided at the time of booking, and our office is also available to assist you on-site if needed.
The tour description also clearly specifies the places and experiences included in the tour, so customers can know what to expect before booking.
We appreciate your feedback and will take your comments into consideration.
Best regards,
my Tour
D
David_B
June 14, 2026 · via Viator
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
Operator response
Dear Customer,
Thank you for your feedback!
We are delighted to hear that you enjoyed the tour, the wine tastings, and the visits to Castellina in Chianti and Monteriggioni. We truly appreciate your words about our guide and driver.
Thank you again for choosing us, and we hope to welcome you again soon.
Best regards,
my Tour in Italy
A
anastasia_b
April 29, 2026 · via Viator
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 · via Tripadvisor
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 · via Viator
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 · via Viator
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 · via Viator
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 · via Viator
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 · via Tripadvisor
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 · via Viator
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.
