Castles & Chianti Wine Experience– Small Group from San Gimignano
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.1/5
Based on 22 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Castles & Chianti Wine Experience– Small Group from San Gimignano worth booking?
Castles & Chianti Wine Experience– Small Group from San Gimignano is a 7-hour experience in San Gimignano, Italy, from $43 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.1/5 rating across 22 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 64 / 100
- Rating
- 4.1/5 (22)
- Duration
- 7 hours
- From
- $43 per person
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 tw
What you get
About this experience
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
What's included
Included
- On-board WiFi
- Olive oil and balsamic vinegar sampling
- Expert multilingual guides
- Snacks
- Alcoholic beverages
- 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
What you'll see and do
Fattoria Lornano
Enjoy a delightful wine tasting experience paired with an informative winery visit.
60 minutes here · Admission included
Castellina In Chianti
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.
60 minutes here
Monteriggioni
Visit the ancient village of Monteriggioni and take some unforgettable pictures.
40 minutes here
Strada Statale 222 Chiantigiana
Enjoy a second wine tasting and visit to a Tuscan winery.
60 minutes here · Admission included
Where it starts and ends
Meeting point
San Gimignano
Piazzale Montemaggio San Gimignano, at the bus stop next to the parking lot
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Piazzale Montemaggio San Gimignano, at the bus stop next to the parking lot
Options you can book
Winter tour
12:00PM: Starting time is different during winter season
Summer tour
1:00PM: Starting time during summer season
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Tue, Thu, Sat
- Group size
- Up to 15 travelers per booking
- Operated by
- myTour in Italy
Know before you go
- 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.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 22 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
10 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Traveler reviews
22 verified traveler reviews for Castles & Chianti Wine Experience– Small Group from San Gimignano. Ratings and reviews provided by Viator and Tripadvisor.
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
Response from the operator: 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
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!!
Response from the operator: 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
via Viator
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.
Response from the operator: 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.
via Tripadvisor
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.
Response from the operator: 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.
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.
Response from the operator: 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.
via Viator
Good to know
- Duration
- 7 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Tue, Thu, Sat
- Price range
- $43 to $85
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 8
- Verdict
- Solid Choice
Why this scores 64
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Castles & Chianti Wine Experience– Small Group from San Gimignano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for San Gimignano.
How much does Castles & Chianti Wine Experience– Small Group from San Gimignano cost?
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Prices start at $43 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Gimignano usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Castles & Chianti Wine Experience– Small Group from San Gimignano take?
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Plan for about 7 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in San Gimignano is not rushed.
Is Castles & Chianti Wine Experience– Small Group from San Gimignano worth it?
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It holds an Outty Ranking of 64 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.1/5 across 22 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in San Gimignano, and how flexible the cancellation terms are.
Can I cancel or reschedule Castles & Chianti Wine Experience– Small Group from San Gimignano?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Castles & Chianti Wine Experience– Small Group from San Gimignano suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 7-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Castles & Chianti Wine Experience– Small Group from San Gimignano?
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Around 8 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in San Gimignano can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in San Gimignano and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.
Where does Castles & Chianti Wine Experience– Small Group from San Gimignano start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central San Gimignano within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in San Gimignano?
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On Outty we rank every San Gimignano experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Wine and food tasting in an organic family winery, Tuscan Cooking Class, Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit San Gimignano?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in San Gimignano?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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