Castles & Chianti Wine Experience– Small Group from San Gimignano
San Gimignano, Italy
- 6 hours (approx.)
- Pickup offered
- Mobile ticket
- Offered in: English
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Overview
Visit two renowned wineries—and enjoy two separate tastings—during this full-day, small-group wine lovers’ tour of Tuscany’s Chianti region. Head to scenic, medieval-era Castellina In Chianti to enjoy Chiani wines paired with traditional cured meats. Then, head to Fattoria Lornano for a chance to sample even more local vintages along with extra virgin olive oil.
- A guided small-group, full-day tour of the Chianti region with two wine tastings
- Get information and background on the region’s wine-making history from your guide
- Tours are capped at only 8 participants for a personalized experience
- Enjoy comfortable, round-trip transportation from a central location in San Gimignano
Sample Menu
Main
Snacks paired with wine
The second wine tasting will be served with some typical Tuscan snacks
What's Included
- Travel in air-conditioned minivan for up to 8 people or minibus for up to 20 people
- Expert multilingual guides
- WiFi on board
- Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
- Alcoholic BeveragesTasting of 7 types of wines in total
- Olive oil and balsamic vinegar sampling
- SnacksLocal products tasting (bread, salami)
- travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
- Gratuities
Meeting and Pickup
You can head directly to the meeting point, or request pickup
Itinerary
1
Fattoria Lornano
1 hour • Admission Ticket Included
2
Castellina In Chianti
1 hour • Admission Ticket Free
3
Monteriggioni
40 minutes • Admission Ticket Free
4
Strada Statale 222 Chiantigiana
1 hour • Admission Ticket Included
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Most travelers can participate
- This tour/activity will have a maximum of 30 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Tom_M
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.
Reviews
4.1
based on 21 reviews
anastasia_b, Apr 2026
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!!
Response from Host, May 2026
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
Olivia_S, Jul 2025
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.
Response from Host, Jul 2025
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.
Nicole_A, Jun 2025
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.
Response from Host, Jun 2025
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.
Ronica_V, May 2025
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!
Response from Host, May 2025
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.
Peggy_L, Oct 2023
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.
Response from Host, Oct 2023
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.
Tom_M, Oct 2023
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.
Response from Host, Oct 2023
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.
Scott_D, Oct 2023
The driver was excellent: friendly, professional, insightful.
Both wineries offered great education and delicious wine.
Response from Host, Oct 2023
Dear Customer,
Thank you for sharing your feedback with us. Glad to know that you had a good time on the tour and enjoyed every part of it. Looking forward to having you again on our upcoming tours in the near future.
Best regards,
My Tour in Italy team.
Victoria_H, Jun 2023
Tour was a bit random and didn't follow schedule but the places (2 wineries) we went were fabulous. Tour guide was pleasant but we made an unexpected detour to Siena to pick up additional passengers which reduced our time at other little towns by 1.5hr
Sue_R, May 2023
It got cancelled I went on another one, I traveled 5-6 hours for 6 very small glasses of wine in 2 wineries. Not happy. It was not made clear to me that I would have to travel from San Gimignano to Seine to pick up the tour. Disappointed. However the Driver/Guide was very good
Alice_S, Feb 2023
To start off, the description isn’t accurate. There were four stops on this tour, not just the two wineries. The other two stops were two small castle towns which were quite charming, but also completely closed. This tour should not be offered in the winter as it is now because those two stops take five minutes tops and in the cold, there isn’t anywhere to go for the remaining 25 minutes you’re there. Additionally, we were picked up in San Gimignano. There was no mention during booking that there was also a pickup in Siena so our tour started with an hour long van ride which would’ve been fine if we were warned, but we were not. Our guide was also very hard to understand and I say that as a native English speaker who is conversational in Italian. My partner was completely lost. The two wineries we stopped at were top notch though and I highly recommend them, just not as a part of this tour
Mara_C, Oct 2022
All the trip was great. Beautiful scenery. We stopped at Monteriggioni and Cappellina in Chianti, both lovely towns. The two wineries we visited were nice country estates. Snacks delicious. Our tour guide and drive, John, was very kind.
Neil W, Jun 2016
Well organised, very knowledgable driver, great tour, great locations. Would recommend it.
Mirco_T, Jun 2022
Die Tour war sehr ausgiebig. Leider gab es die ganze Zeit nichts zu trinken, auch bei den Degustationen nicht. Die Landschaften waren sehr schön und unser Guide hat sich viel Zeit genommen uns viele Infos zu geben.
Response from Host, Jun 2022
Dear Customer,
first of all thank you for choosing us and leaving this feedback.
We need all of our customer reviews because is like this that we improve our service for next journeys.
Thank you!
Best Regards
My Tour
From $101.55
per personup to 24 hours before the experience starts (local time)
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