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Small-Group Chianti Wine-Tasting and Castles Trip from Siena provided by Tuscan Escapes - Day Tours

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Small-Group Chianti Wine-Tasting and Castles Trip from Siena

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2 adults
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Low Price Guarantee
This is the ideal tour for wine lovers, and architecture fans. Save hours of research and planning time, and go on a comprehensive small-group tour to Chianti. See spectacular countryside views, and visit Castello di Brolio—a historic castle and the birthplace of Chianti wine. This stress-free tour including multiple winery visits, wine tastings, and a delicious Tuscan lunch.
You'll start at
Piazza San Domenico
Piazza S. Domenico, 53100 Siena SI, ItalyMeet under the large tree next to the red brick church
See address & details
  • 1
    Castello di Brolio
    Stop: 50 minutes - Admission included
    See details
  • 2
    Castello di Vertine
    Stop: 20 minutes -
    See details
  • 3
    Radda in Chianti
    Stop: 40 minutes -
    See details
You'll end at
Piazza San Domenico
Piazza S. Domenico, 53100 Siena SI, ItalyMeet under the large tree next to the red brick church
See address & details
  • Combine wine tasting and visits to medieval castles on this Chianti day trip
  • Travel with ease between countryside sights in an air-conditioned vehicle
  • Small-group tour with a limit of eight travelers
  • Enjoy the perk of having wine tastings and a delicious Tuscan lunch included
Important Information
Departure Point
Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy
Return Details
Returns to original departure point
  • Professional guide
  • Lunch
  • Wine tasting
  • Air-conditioned vehicle
  • Entry/Admission - Castello di Brolio
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance to Castello di Brolio
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Additional Info
  • 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
  • This experience requires a minimum number of travellers. If it’s cancelled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
  • This tour/activity will have a maximum of 8 travellers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveller rating
  • 13
  • 1
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Traveller type
Time of year
Popular mentions
Barb M wrote a review Oct 2019
1 contribution1 helpful vote
David our tour guide made us feel comfortable and welcome. He was very knowledgeable and took us to three fabulous wineries. They were all different but each one had experienced owners that we learned so much from. The wine and the food were exceptional. We highly recommend this
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Date of experience: October 2019
1 Helpful vote
Peter T wrote a review Sep 2019
Jindera NSW3 contributions1 helpful vote
Most amazing experience. Our guide was so knowledgeable and went out of his way to make this a day we will never forget. Beautiful wines, beautiful food, spectacular countryside and villages, magnificent wineries and amazing company. Many thanks Tuscan Escapes.
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Date of experience: September 2019
Jo&steve wrote a review Aug 2019
4 contributions
We had the most amazing tour of Siena with William. It was a very personalised tour as there was only the two of us on the day His knowledge of the Tuscan area was outstanding. He answered our questions with patience and enthusiasm. The castle and wineries we visited were
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Date of experience: August 2019
ASingleJulie wrote a review Jul 2019
Saint Louis, Missouri42 contributions10 helpful votes
My family loved this tour! We had a great guide--very friendly and talkative, full of interesting information about the history in Tuscany. We went to a number of amazing locations, including wineries and a fantastic restaurant! The number of people included was also small, so
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Date of experience: July 2019
Suzanne S wrote a review Jun 2019
2 contributions
Absolutely would recommend this tour!!! Our guide David was knowledgeable and so enjoyable! We saw everything as promised and then some! Educational and TONS of fun!
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Date of experience: June 2019
About the operator

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

By: Tuscan Escapes - Day Tours
Couldn't have been better!
We spent 4 days with Tuscany Escapes in September’19 and had a fabulous time. We’re ashamed it’s taken us so long t
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Rob-Bob C
Private Tour from Florence to Siena with San Gimignano
Our guide, Giada, was spectacular! On time pickup, incredibly knowledgeable on the two sites (and points between).
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Beautiful hike through the Tuscan hills
My husband and two adult children loved our hike last June. The guide was great and talked about the area and the h
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Amazing wine tour with Davide Dionisi
We went on a sunset Wine Tour with Davide, last minute booking but absolutely THE best tour we had in Tuscany. Davi
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Tuscan Escapes Brunello Wine Tour
My wife and I had an exceptional day with Giorgia on this imersive tour. She is a very knowledgeable guide teachin
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Well planned walk through Sienna.
Pleasant walk through Sienna. Our GUI was extremely knowledge and communicated well in English. I highly recommend.
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A Day Under the Tuscan Sun
Wow. What an amazing experience we had. First: Small group, which is very nice. We were lucky and had such a fun gr
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Great sites, well organized, tour guide cranky
I'm traveling with my sister, brother in law and 20 year old niece for a couple of weeks in Italy. I really wante
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Andrew R
Incredible experience we will never forget
Highly recommend this day trip to do some wine tasting, tour a few Montalcino wineries, and have the time of your l
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Amazing day
We had a wonderful time on this tour. There were just 4 of us in total which was perfect. Our tour guide/driver was
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Karen H
Spectacular walking tour MUST DO!
Our tour guide Sylvia was wonderful. Her knowledge of Sienna provided us an in depth understanding of the history u
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Janet M
A Great Day!
If you are in the area don’t miss this one. The tour operator could not have been more accommodating, even going ou
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Siena Walking Tour Viator
Marela was a great tour guide, clearly explaining the 3 centers of power in medieval Siena: Banks, Government, and
Read more
Amazing!!! 10/10
We had a fantastic trip! Our tour guide David was both exceptionally knowledgeable and also just fun. They were ver
Read more
Outstanding Wine Tour
Our tour guide, Danny, was outstanding! He was extremely knowledgable about winemaking and about Montalcino wines a
Read more
Key Details
  • Duration: 8h
  • Mobile Ticket Accepted
  • Free Cancellation up to 24 hours in advance
  • Instant Confirmation
  • Languages Offered: English
Why Book on Tripadvisor?
  • Reserve Now & Pay Later
  • Free Cancellation up to 24 hours in advance
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Frequently Asked Questions about Small-Group Chianti Wine-Tasting and Castles Trip from Siena