San Gimignano Chianti and Castle Tour: Exploration of Iconic Tuscan Wine Region

Embark on a captivating tour of the iconic Tuscan wine region, exploring San Gimignano, Chianti, and a castle. Indulge in wine tastings, savor typical food, and immerse yourself in the picturesque Tuscan scenery.

Duration: 6 hours
Cancellation: 24 hours
Highlights
  • Fattoria Lornano - Savor a delightful wine tasting experience complemented by an insightful winery tour.
  • Castellina In Chianti - Castellina in Chianti is a picturesque village nestled in the heart of Tuscany, celebrated for its rich history, scenic landscapes, and local cuisine. Visitors can explore historic sites, enjoy local delicacies, and…
What's Included
  • On-board WiFi
  • Olive oil and balsamic vinegar sampling
  • Tasting of 7 types of wines in total
  • Expert multilingual guides
  • Snacks
  • Travel by air-conditioned minivan
  • Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
What's Not Included
  • Gratuities
Additional Information

Come and explore the splendid region of Chianti with us! Allow yourself to be enveloped by the quintessential Tuscan landscape you have always dreamt of. Chianti’s unique identity is reflected in its vibrant ruby-red hue and characteristic violet-scented bouquet, setting it apart as one of the globe’s most renowned wines. During the tour, you’ll…

Location
Porta San Giovanni
Via San Giovanni
In front of Porta San Giovanni
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.2
(18 Ratings)
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1 star
Nicole_a
Jun 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.
Review provided by Viator
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!
Review provided by Viator
Peggy_l
Oct 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.
Review provided by Viator
Tom_m
Oct 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.
Review provided by Viator
Vgpm
Oct 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)
Review provided by Tripadvisor
Scott_d
Oct 6, 2023
The driver was excellent:... - The driver was excellent: friendly, professional, insightful. Both wineries offered great education and delicious wine.
Review provided by Viator
Victoria_h
Jun 25, 2023
Lovely canter through Chanti - 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
Review provided by Viator
Sue_r
May 27, 2023
Not the best - 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
Review provided by Viator
Alice_s
Feb 21, 2023
Description is inaccurate - 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
Review provided by Viator
Valdirferreirar
Oct 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.😡
Review provided by Tripadvisor
From $98
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).