Tours and Tickets

Small-Group Chianti and San Gimignano Sunset Trip from Siena provided by Tuscan Escapes

LIKELY TO SELL OUT*

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Small-Group Chianti and San Gimignano Sunset Trip from Siena
5
Book in advance
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$174.06
per adult
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100% of travelers recommend this experience
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Tour snapshot
Travel in the comfort of an air-conditioned vehicle
Duration:
8–9 hours
Taking Covid-19 safety measures
Group size:
8
Stroller accessible
Ticket type:
Mobile
Free cancellation
  • Duration:
    8–9 hours
  • Taking Covid-19 safety measures
  • Group size:
    8
  • Stroller accessible
  • Ticket type:
    Mobile
  • Free cancellation
About
Experience the beauty of Tuscany and sample some of the area's celebrated wines on this sunset dinner tour from Sienna. Stops along the way include the town of Monteriggioni, with its 13th-century fortifications, as well as San Gimignano, known for its beautiful medieval architecture. Your last stop is a traditional Tuscan farmhouse, where you sit down to a local dinner, before returning to Sienna.
Know before you go
  • Duration: 8-9 hours
  • Mobile tickets accepted
Cancellation policy
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Available languages
English, Italian
Highlights
  • A professional guide is on hand to provide commentary
  • Taste local wines at a Tuscan winery
  • A traditional Tuscan dinner is served at a local farm
What to expect
Know before you go
  • Duration: 8-9 hours
  • Mobile tickets accepted
Available languages
English, Italian
Cancellation policy
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Highlights
  • A professional guide is on hand to provide commentary
  • Taste local wines at a Tuscan winery
  • A traditional Tuscan dinner is served at a local farm
What to expect
Need help booking?
Call the number below and use the product code: 5493CHIANTISUNSET
Important information
Inclusions
  • Professional Guide
  • Transport by air-conditioned minivan
  • Tour of winery with wine tasting
  • Traditional dinner at farm
  • Entry/Admission - Chianti Road
Exclusions
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance fees to attractions in San Gimignano
Duration
8–9 hours
Departure details
  • Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Meet under the large tree next to the red brick church
Additional information
  • Confirmation will be received at time of booking
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers
Inclusions
  • Professional Guide
  • Transport by air-conditioned minivan
  • Tour of winery with wine tasting
  • Traditional dinner at farm
  • Entry/Admission - Chianti Road
Exclusions
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance fees to attractions in San Gimignano
Departure details
  • Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Meet under the large tree next to the red brick church
Duration
8–9 hours
Return details
  • Returns to original departure point
Additional information
  • Confirmation will be received at time of booking
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers
Travel safe during COVID-19
Last updated: Mar 13, 2022
A note from Small-Group Chianti and San Gimignano Sunset Trip from Siena
All travelers will have to wear their own personal protective equipment (masks covering nose and mouth).
What you can expect during your visit
  • Guides required to regularly wash hands
  • Hand sanitizer available to travelers and staff
  • Transportation vehicles regularly sanitized
What you can expect during your visit
  • Guides required to regularly wash hands
  • Hand sanitizer available to travelers and staff
  • Transportation vehicles regularly sanitized
  • Face masks required for guides in public areas
  • Paid stay-at-home policy for staff with symptoms
  • Gear/equipment sanitized between use
  • Face masks required for travelers in public areas
  • Social distancing enforced throughout experience
Itinerary
  • You'll start at
    Piazza San Domenico
    Piazza S. Domenico, 53100 Siena SI, Italy
    Meet under the large tree next to the red brick church
    See address & details
  • Pass by
    Basilica Cateriniana Di S. Domenico
  • 1
    Cantinetta di Monteriggioni
    Stop: 30 minutes
    See details
  • 2
    Historic Centre of San Gimignano
    Stop: 60 minutes
    See details
  • 3
    Chianti Road
    Stop: 2 hours - Admission included
    See details
  • You'll return to the starting point
+
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions

5.0
13 reviews
Excellent
13
Very good
0
Average
0
Poor
0
Terrible
0

Steve A
1 contribution
Apr 2022 • Friends
I was exploring Tuscany with my brothers and we were fortunate to discover Tuscan Escapes. We spent an afternoon and evening with our guide William who provided many interesting insights into the culture, history, and wine of the region along with a lot of laughs. The first stop was Il Poderino, a boutique Chianti estate, where we sampled 5 Chianiti’s of different vintages and a vin Santo, all accompanied by local charcuterie. Next we made a quick stop at the walled town of Monteriggioni before arriving at San Gimignano for 90 minutes of free time to explore the medieval town. Finally, we landed at Il Castagnollino for an exceptional 5 course meal of local cuisine paired with wine. This day trip is a must for anyone visiting Siena and I would highly recommend asking for William as the guide.
Written April 13, 2022
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

l-globetrotter
London, UK3,824 contributions
Jul 2021
Firstly, i have never dealt with YourGuide that i used to book this, or for that matter Tuscan Escapes, both were excellent. Giorgia from Tuscan Escapes was always on standby to help with any questions, and when one tour got cancelled found me an alternative that I very much look forward to going on, especially in light of yesterdays experience on this Chianti and San Gimignano tour. We had Daniele as a guide, who is great fun, vibrant, funny and very knowledgeable. The man knows a lot about wine, and happily shares it, but yet gives you enough flexibility and free time on the tour for you to make it your own experience. I absolutely loved Lornano winery we visited, both the guide and the owner were absolutely excellent, and location is gorgeous, wine tasty, and you bound to walk away with some fab purchases. We visited Montereggioni tiny walled city, that was not a long stop but enough to enjoy and coffee and bit of sightseeing. San Gimignano was fab fun, we essentially had free time there, I felt it was very well paced. Dinner at the agriturismo was in a beautifully set farm, food homey, and it was tasty and fun because I had two fabulous companions on the tour that I really liked, we event went for a drink in Siena afterwards. I heartily recommend this tour if you are short for time, love your wine and want to have a nice and diverse day.
Written July 25, 2021
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Todd A
Port Hope, Canada53 contributions
My brothers and I signed up for this tour and couldn’t have been happier. William was our guide and he was excellent. Not only was he knowledgeable in wines but also in history, politics, and culture. He was funny and had a story for every occasion. The farms we visited were hospitable, the hosts were gracious and passionate about their offerings, and the wines were delicious. An absolute must when travelling to this area.
Written April 13, 2022
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Paint-by-number
Grand Marais, MN228 contributions
Thank you Elena....please forgive my spelling if incorrect....for two fabulous tours. Your easy going, efficient, fun-loving manner was a pleasure to be around. Greatly appreciated your professionalism in driving and care for our safety.
Loved the Brunello tour...tasted some of the best wine of my lifetime. Interesting, individual and unique vineyards. Loved lunch at the second visit...so very personal.
The San Gimignano tour was also very special. Great wine and an incredible meal. Loved the walk through this lovely town.
I highly recommend these tours and this company. Hope you’re fortunate enough to get Elena as a guide. Cheers!
Written April 27, 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Joaquin Posada
1 contribution
My wife and I got this tour as a present from some good friends in our honeymoon, we didn’t know what to expect and are usually not very enthusiastic about tours and groups. Turns out it was one of the best days of our entire trip. Our guide David was knowledgable, intelligent, respectful and had a great sense of humor, a real professional who makes the experience memorable. The group was small and fun, and the places we visited amazing; an authentic Tuscan experience filed with good taste, beautiful people, food, wine and landscapes. I would definitly do it again and recomend. Well done guys.
Written October 13, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

AKChaney
2 contributions
Sep 2019 • Couples
We had an incredible time with David as our tour guide. We learned a lot, tried a lot of great wine and ended with an unforgettable meal as the sun set over San Gimignano. I would highly recommend this tour - or anything else David leads. It was easily the highlight of our two week trip!
Written September 22, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Mark W
San Francisco, CA50 contributions
May 2019
OK, so we didn't have the best weather, but we had a great group of people and David a wonderful guide. The tour sights were fun and beautiful. You had enough time to do some exploring of San Gimignano take lots of photos. But the star of the evening was the dinner itself! By the time you got to the farm in the Tuscan hills you were ready for food and food you got--an amazing on-going parade of very tasty courses which ended with a wonderful desert and Limoncello or Grappa. Oh yes--there was a sunset to behold. (must be spectacular on a good weather evening. This Is a Tour I will tell all my friend is a must. Thank You Tuscan Escapes you never disappoint!!
Written May 26, 2019
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Eurotravel
New York City, NY6 contributions
This was an amazing experience. The tour guide Ellena was absolutely incredible, warm, knowledgeable and friendly. The people who own the vineyard were so nice and gracious! The wine tasting experience was excellent. They treated us to a wonderful spread of cheese and meats along with their great wine.

We visited two great medieval towns where we were given time to walk around and explore. San Gimignano was incredible to explore.

The best part of the tour came at the end where we went to a family-owned farm and restaurant and were treated to an amazing Italian dinner. We dined outside where we had great views of San Gimignano. The food was great.

We had the opportunity to view and photo a beautiful sunset from the farm during dinner.

This tour was the highlight of our trip to Italy this year!!!
Written June 10, 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Janice H
7 contributions
Jun 2018 • Friends
We were a group of 6 friends in one minibus with our guide David who took us to the wine tasting which was the best one we had been to. David took us to Fort Montiggori and then to San Gimingnano where we had an hour to walk around the beautiful town. The icing on the cake was the farm overlooking San Gimingnano where we had our sunset dinner the location, the food, the wine and the company were amazing!

Unfortunately, near the beginning of our trip our friend was taken ill but David took him and his wife back to our hotel and called an ambulance for him - both David and Eleanor were very caring and helpful for which we were grateful. We would thoroughly recommend this tour especially with this company and especially these 2 guides.
Written June 9, 2018
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Michael A
Toronto, Canada4 contributions
This was an outstanding experience. It began with a visit to a small, family-run winery (“Il Poderino”) in Chianti, where we tasted five wines accompanied by plates of prosciutto, percorino, and bruschetta. We finished with Vin Santo and cantucci. We then visited the historic, walled-town of Monteriggioni and the gorgeous, mediaeval town of San Gimignano. The experience culminated with farm-to-table dinner at a local agriturismo (“Il Castagnolino”) where we were treated to five-course meal prepared by the lovely owner, Carmela. The thing that made it outstanding though was our five-star guide Guglielmo (“William”) who entertained us throughout the entire adventure with humour, stories, history, and fascinating bits of local trivia. Thank-you, thank-you, thank-you to him for truly making this a wonderful day! I wish I could leave ten stars!
Written April 13, 2022
This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.

Showing results 1-10 of 12
*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.
About the operator

Don’t take it from us – here’s what people have to say about this operator.

By: Tuscan Escapes
X6785PBtomh
X6785PBtomh
00
Wonderful hike thru Tuscany Hillside ending at the Monteriggioni Castle for wine tasting🍷
Our guide can’t spell his name but sounded like Techa (so?) was very knowledgeable and provided great comments abou
t_tran33
t_tran33
00
Awesome tour!
We cannot say enough good things about this tour and our tour guide, Mattia! If you are on the fence about booking
546samim
546samim
00
Fantastic
We had a fantastic time learning about the region and the wine. Our guide Mattia was amazing and our group was very
CNBCUpstateNY
CNBCUpstateNY
00
Fabulous day Out!
This was a fabulous day out in the Tuscan countryside. Our guide Guglielmo was fantastic. Not only did he bring u
404johnb
404johnb
00
Highly Highly Recommend!
We had a wonderful Siena & Duomo City Tour with Marella. She was absolutely delightful and very passionate about he
nathaliem27
nathaliem27
00
Perfect day tour to get a taste of Tuscany!
We booked this tour because we wanted to get a taste of Tuscany without having to deal with renting a car. This day
1974jenniferr
1974jenniferr
00
Fun, informative trip!
This tour was wonderful! Guillermo was so thoughtful and caring. He did not rush us and answered every question we
angelopL5070VO
angelopL5070VO
00
Brunello Wine experience
Our guide was knowledgeable and very helpful. He took us to dreamy Tuscan landscapes and a great wine experience. I
kbinsb
kbinsb
00
Epic
This was one of our best experiences in Europe ever. We’ve been visiting Europe regularly since 1987 so we don’t ta
Synchro12
Synchro12
00
The only way to tour Tuscany!
We booked a small group eBike tour with Tuscan Escapes and it was a highlight of our entire trip. The Tuscan spring
Louise C
Louise C
00
Glorious Tuscany
What an amazing tour. Spend a glorious day in Tuscany. Our guide Daniel was the perfect guide for our small group
694KARENA
694KARENA
00
Sunset Dinner Tour - Top Notch
Our party of four went on the Chianti and San Gimignano Sunset Tour with Dinner. Our small group tour guide - Will
manuelz897
manuelz897
00
Siena in a morning...........
We were a small group of 4 persons. we enjoyed every minute of the tour. A spècial thank and congratulation to the
Meander65090172923
Meander65090172923
00
Phenomenal Day
The most phenomenal day enjoying the countryside with our guide Mattia! Not only is he your guide he is an experien
Barbara M
Barbara M
00
Always Wonderful: Sunset Tour of Chianti including San Gimignano
This is the third time we've taken this tour. Even though the weather was miserable, it was still a wonderful after
Frequently Asked Questions about Small-Group Chianti and San Gimignano Sunset Trip from Siena

Small-Group Chianti and San Gimignano Sunset Trip from Siena will start at 2:30 PM. Discover and book Small-Group Chianti and San Gimignano Sunset Trip from Siena on Tripadvisor


Small-Group Chianti and San Gimignano Sunset Trip from Siena price starts from $174.33. Discover and book Small-Group Chianti and San Gimignano Sunset Trip from Siena on Tripadvisor

Small-Group Chianti and San Gimignano Sunset Trip from Siena cancellation policy: For a full refund, cancel at least 24 hours in advance of the start date of the experience. Discover and book Small-Group Chianti and San Gimignano Sunset Trip from Siena on Tripadvisor