Small-Group Chianti Wine-Tasting Trip from Siena

Badge of ExcellenceSiena, Italy
Likely to Sell Out

From $173.92

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 8 hours (approx.)
  • Mobile ticket
  • Offered in: English


Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.
  • Full-day trip to Chianti from Siena with an expert guide
  • See dramatic Italian castles and learn of their strategic importance during medieval wars between Siena and Florence
  • Tour Castello di Brolio and its impressive vineyards
  • Enjoy a Tuscan lunch and a wine tasting at Castello di Ama
  • Small-group tour (maximum eight people) provides a unique and intimate experience

What's Included

  • Professional guide
  • Lunch
  • Wine tasting
  • Air-conditioned vehicle
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance to Castello di Brolio

Meeting And Pickup

Meeting point

  • Piazza San Domenico
    Piazza S. Domenico, 53100 Siena SI, Italy

    Meet under the large tree next to the red brick church

Start time

09:30 AM

End point

This activity ends back at the meeting point.

What To Expect

Depart from central Siena in a luxurious, air-conditioned minivan destined for the rich wine region of Chianti. Admire the gorgeous countryside thronged with olive groves, ancient castles, and cypress trees as you listen to illuminating commentary from your professional guide. 

Feel your intrigue heighten as you approach the enchanting Castello di Brolio, a medieval castle that enjoys a vertiginous hilltop perch. Gain fascinating insight into the fortress’ turbulent history and hear tales of bloody battles and the castle's radical transformation. Embark on some pleasant exploration of the beautiful vineyards, reputed birthplace of fine red wine, Chianti, and pose for photographs among the gorgeous surroundings.  

Travel onward to Castello di Vertine, a once-fortified medieval village.

Continue to Castello di Ama, to explore its winding streets, tuck into a Tuscan lunch, and enjoy a wine tasting.

Then return to your vehicle for the relaxing ride back to Siena.

Castello di Brolio

50 minutesAdmission Ticket Included

Castello di Vertine

20 minutesAdmission Ticket Free

Radda in Chianti

40 minutesAdmission Ticket Free

Additional Info

  • Confirmation will be received at time of booking, unless booked within 16 hours of travel. In this case confirmation will be received as soon as possible, subject to availability
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • Not wheelchair accessible
  • Stroller accessible
  • Service animals allowed
  • Infant seats available
  • No heart problems or other serious medical conditions
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
Susan S
While this was our first time taking a guided wine tour it was not our first wine tour we're from the SF Bay Area, close to hundreds of wineries. It was a fabulous tour. We tasted wine, olive oil and incredible food. We met owners, makers, growers. We learned about the industry, the history of wine in the Chianti region, visited enchanting small towns, touched the vines and the soil, saw artwork, villas, estates... The five of us were overwhelmed with charm, information, food, wine and the richness of an informative tour guide. We'll be back.


48 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 48 reviews
Excellent Tour
Kathy_C, May 2023
Truly enjoyed the day. Mattia was an excellent guide - loves wine and is incredibly knowledgeable. Right mix of stops and driving. Good number of people. Wonderful wine, food and time had by all. Highly recommend!
Beautiful tour of Chanti Classico region
Arlene_D, May 2023
Daniel was very informative. A little disappointed that after 5 hours on a wine tasting trip we had had only one taste of wine. When we arrived at the 2nd would have been nice to have been given a taste while listening to how wine is made. Wish we knew lunch was not going to be until 2:00. Lunch was great. Water in the van would be nice. We would definitely recommend.
A spectacular day of wine...
Timothy_P, Oct 2022
A spectacular day of wine tastings and food pairings with a very knowledgeable guide/driver. A wonderful experience!
Tuscany vineyards
Alan_G, Sep 2019
Fabulous tour with Daniel, his knowledge and humor were unbelievable. He made our tour so special. Highly recommend Tuscan Escapes for your tours.
Amazing tour!!
Gerald_M, Apr 2019
Our tour guide Elio did an amazing job. Lunch and the wine were also very good. We saw 3 different castles and had a great tour.
Amazing tour!
Climber812058, Nov 2018
Bravo Danielli. Very informative and entertaining tour. Danielli has an intimate relationship with the vineyards we visted and deep knowledge of winemaking and Toscano. Fantastic tour.
While this was our first time taking...
Susan S, Jul 2018
While this was our first time taking a guided wine tour it was not our first wine tour we're from the SF Bay Area, close to hundreds of wineries. It was a fabulous tour. We tasted wine, olive oil and incredible food. We met owners, makers, growers. We learned about the industry, the history of wine in the Chianti region, visited enchanting small towns, touched the vines and the soil, saw artwork, villas, estates... The five of us were overwhelmed with charm, information, food, wine and the richness of an informative tour guide. We'll be back.
An excellent tour of the Chianti...
Sam_R, Oct 2017
An excellent tour of the Chianti region. Our guide, Daniel, was absolutely terrific. Very knowledgeable and accommodating. The small size of the tour was very imitate.
We loved this tour so much we booked...
Joel R, Sep 2017
We loved this tour so much we booked another one to a different wine region the very next day. My husband and I wanted to do a wine tour but had no idea where to go and driving your own car in the Sienna area is no piece of cake. We got online and found this tour through Viator.Com . It is an all day adventure from 9:30am to 6:00pm. We met our guide at a church in Sienna called San Domenico Basilica. We were greeted by Elena, our guide. There were 8 people booked for our tour but there ended up being only 6 of us. We rode in a spacious van that easily accommodates 8 plus the driver. On our way to our first destination, a huge castle on the hill, Elena stopped far below the castle for a picture opportunity. We were awestruck by the beauty of the Tuscan valley in all its glory. Next stop was wine tasting at Castello di Briolo, same name as the castle above it. You can ship wine back to the US most states, anyways from this winery. We were then on the move again through winding hills and amazing scenery on our way to the small town named Radda. There we strolled through the narrow streets taking in the wonderful atmosphere and doing a little souvenir shopping. By now we were all starving but not to worry. Once we arrived at the winery of Ristoro di Ama we were treated to the most delicious lunch. From a impressive menu we chose the roasted pork, gnocchi, and salad. It was all amazing and the people who ran it were most gracious. We had 3 wines to taste here. They also ship wine to the USA. Our last stop we visited the winery of Il Poderino. Here we were given a tour of the wine making area. We also tasted 3 wines here and the owners were also so very hospitable. Again, they also ship wine, From here we ventured back to Sienna to end our most delightful tour. Elena, our guide, was great! She was delightful from start to finish and really made this tour top notch. We would highly recommend it to anyone coming to this area to visit.
It was a wonderful trip. Daniel the...
David E, Sep 2017
It was a wonderful trip. Daniel the guide was very knowledgeable about vine making and we lernt a lot from its basic chemistry up to the vine politics. He also showed us the beautiful Chianti region. On in all it was a great experience.
We ended up being alone so very...
Susan M, Feb 2017
We ended up being alone so very private. Guide was great!!! All stops, especially lunch, wineries, etc over the top!!!!
Outstanding day with a great tour...
Patricia B, Oct 2016
Outstanding day with a great tour guide who knew how to get around and the luncheon was magical at the castle. The wine tasting was exceptional! The small group environment was perfect and we had a chance to meet some very nice people!
Great tour led by an exceptional...
Neil G, Sep 2016
Great tour led by an exceptional guide. We met in Siena at San Domenico and rode the minibus out into Chianti for a fun outside tour of Castello Brolio and its vineyards. We enjoyed tastings at two wineries and had lunch outside in a beautiful Tuscan setting. Our guide was extremely knowledgeable and kept it interesting all day. Highly recommended!
Danielle was amazing. This was the...
Katrin W, Jul 2016
Danielle was amazing. This was the highlight of our three week trip to Italy Rome, Siena, Florence, Chianti, and Venice. Danielle was friendly, insightful, and relaxed. There were only four of us on this tour, and we had the most amazing day -- learning about the countryside, boar hunting, wines, the culture and history of Chianti wine, the agriculture, etc. I can't recommend this tour enough. It was incredible.
We had an excellent time on the...
Scott C, Sep 2015
We had an excellent time on the tour. We felt we visited areas that were not touristy, where we were not combined with other tour groups either. We loved our tour guide. He was knowledgeable, easily approachable and cared about whether we were enjoying ourselves. A great experience overall!
Our tour guide Leonardo is very...
Stephen A, Sep 2015
Our tour guide Leonardo is very knowledgeable about the areas culture and tradition- the Tuscan way of life.Our trip to Chianti Classico was a delightful escape and I highly recommend it
Daniele could not have been a better...
Sandie T, Oct 2014
Daniele could not have been a better guide not to mention provided endless information about the production of wine. I highly recommend this tour.
Great tour, great wine, great...
Robert G, Oct 2013
Great tour, great wine, great guide. We had a marvelous time with our guide, Daniele, and the rest of the folks on our bus. We were comfortably driven around much of the Chianti region visiting the Ricosoli Estate and enjoyed a wonderful lunch and tasting at the Montechiaro estate. Do yourself a favor and take this tour when you're in Tuscany. It may very well have been the highlight of our entire Italian two week holiday!
Wonderful tour. Our guide Daniele...
Rosemary A, Jun 2013
Wonderful tour. Our guide Daniele was very knowledgable and patient. The farms we visited were beautiful and of course the wine was outstanding! With only 4 people on the tour it was relaxing and a lot of fun!
Absolutely excellent. Milo was a...
Ian H, Nov 2012
Absolutely excellent. Milo was a great tour leader. The wineries we visited were great. I would highly recommend the tour.
Great guided tour. Enjoyed meeting...
edward h, Oct 2012
Great guided tour. Enjoyed meeting the winemakers at the first two wineries and touring the castle at the last winery. Would recommend to others.
It was a great day! Beautiful...
Olin S, Oct 2012
It was a great day! Beautiful weather. A small group of 3 of us. Driver was great! The learning about wine was fascinating. Highly recommend this tour!
My husband and I totally lucked out...
rnerin, Jul 2012
My husband and I totally lucked out with this tour as we were the only 2 people, so we had our own private driver, Milo, for the entire day!Even had that not been the case, the tour was fabulous!! Milo was an excellent guide-very pleasant and knowledgable about wine, the regional geography, flora and fauna and history. As you would imagine, the Chianti region is beautiful (and the wine isn't bad either!). We had three tastings, one large (where we ran into an American expat who grew up around the corner from where we live!) and two which were with small wineries where we met and were able to chat personally with the winemakers. Lunch at one of their homes, in the garden (with the family and some buyers from the Netherlands was absolutely fantastic-FRESH pesto pasta made by Nona and cherries right from the tree!). It is no surprise that we shipped a case of wine back to the states (along with some olive oil and vinegar)! We HIGHLY recommend this tour!
Fantastic Excursion! Our tour guide...
Frederick D, May 2012
Fantastic Excursion! Our tour guide Milo was extremely knowledgeable and made the day truly enjoyable. Yes, you see a castle and tour one, but the wine tasting experience really made it. At one winery the 5th generation owner and winemaker toured us around and then sat with us and talked about wine for an hour as he poured us several healthy tastes of his work.

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