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Small-Group Chianti Trip with Wine Tasting from Siena

Recommended by 100% of travelers
Badge of Excellence
Siena, Italy
  • 8 hours (approx.)
  • Mobile ticket
  • Offered in: English

Overview

Avoid the stress of navigating winding country roads or unfamiliar public transit on your own and instead discover the fine wines and rich historical heritage of Chianti on this full-day trip from Siena. Travel through the Tuscan countryside to Castello di Brolio in the heart of the Chianti wine country for guided tasting sessions and a traditional Italian lunch. Enjoy the intimate atmosphere of a small group capped at 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 in front of the church steps of the San Domenico red brick church (also called Basilica Cateriniana)

End point

This activity ends back at the meeting point.

Start time
.9:30 am

Itinerary

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.
1

Castello di Brolio

50 minutes • Admission Ticket Included

2

Castello di Vertine

30 minutes • Admission 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.

Traveler Photos

Gallery picture 1 (from a traveler's review)
Gallery picture 2 (from a traveler's review)
Gallery picture 3 (from a traveler's review)
Gallery picture 4 (from a traveler's review)
Gallery picture 5 (from a traveler's review)

Featured review

Janice_K
If you are looking for an all-day wine tour that visits more than one winery this is a great option. The tour stops at three wineries. The first two were my favorite. The second tour included an excellent lunch. Our driver/host was knowledgeable and explained the pyramid of wines and we traveled. He was very courteous and gave the group options on how long we wanted to stay.

Reviews

5.0
based on 82 reviews
Total reviews and rating from Viator & Tripadvisor
Sort by: Most insightful

Very thoughtful itinerary...

Mark_J, Oct 2025
Very thoughtful itinerary with a knowledgeable guide. Marco was great! We learned about winemaking, the Chianti Classico region, and its people. Lunch was amazing and beautifully presented.

Excellent wine tour

Janice_K, Sep 2025
If you are looking for an all-day wine tour that visits more than one winery this is a great option. The tour stops at three wineries. The first two were my favorite. The second tour included an excellent lunch. Our driver/host was knowledgeable and explained the pyramid of wines and we traveled. He was very courteous and gave the group options on how long we wanted to stay.

Wonderful experience....

Lori_S, Sep 2025
Wonderful experience. Loved visiting small family owned/operated wineries. People were exceptionally friendly and hospitable. Julia was a lovely guide. Lunch, cooked by”Mama”, was beyond imagination. This day will go down as one of the best of our Italian holiday. By the end of the day I felt like we had been with family.

Wonderful wine tour

Jessica_S, Jul 2025
We didn't actually do the chianti tour because there wasn't enough people on it, so we were switched (after checking with us and giving us the option of cancellation) to the brunello di montalcino tour (but to save on admin the booking wasnt switched over so i cant review the tour i actually did!!) . I can't say how the chianti tour was but the brunello tour was 12/10 and overall it was great to see and taste wines that are overall probably of a higher quality/rarity. Our driver and tour guide, Emmanuele was also so great and knowledgeable and a safe driver. This tour was our favourite day so far and well worth the price. I would imagine the chianti tour was as good!

Tuscan Escapes Day Tour.

kathy_b, May 2025
Keko, our guide, was fantastic. The tour was also small so it felt very personal. The three wineries we visited where also well chosen. We would recommend it.

Paolo was an extremely...

Dawn_A, May 2025
Paolo was an extremely entertaining and knowledgeable guide. We had a fascinating insight into the Chianti region past and present. The lunch at a small family winery was out of this world.

Fantastic tour, highly recommended

Stephen_O, May 2025
Marco was an excellent and knowledgeable driver and guide. The 3 winery visits were very good, in particular the two small family ones. The lunch at the Azienda Agricola Casanova di Bricciano was superb, and we bought a case of their very nice Chianti Classico Riserva. It was a lovely introduction to the Tuscan countryside.

Small Group winery tour of Chianti

Andrea_P, May 2025
What a wonderful experience we had traveling with this tour. Our guide and driver Francesco (Keko) was a knowledgeable and informative host. We were picked up on time at the designated meeting spot and quickly began our journey through the Chianti region of Tuscany . All through the drive Keko gave historical and current information. Our first stop was a tour of the castle grounds at Riccasoli followed by a tasting of their wines. Next was a quick visit to the charming town of Radda, where we wandered freely for a bit, giving a chance to shop. Then on to our second winery where we had a tour of the cellars, an explanation of the wine making process and a delicious 4 course lunch accompanied by a wine tasting for each course. Both the food and wine were delicious and generous. Our final stop was a tour and tasting of yet another winery. All in all a very complete tour I highly recommend.

Great Chianti tour

Dana_L, Oct 2024
A great tour of the Chianti region of Italy. We enjoyed visiting the small Vineyards and the lunch was so delicious! I highly recommend this tour

Best Wine Tour Ever

Peggy_M, Sep 2024
This is the best wine tasting tour we’ve ever been on. We visited 3 boutique wineries, one of which included an excellent lunch. In addition we toured a castle and visited a small town. Our guide Julia was fantastic, informative and spoke English very well. I highly recommend this tour.

Excellent Chianti vineyard tour

Rosemary_R, Jun 2024
Very knowledgeable, personable driver and a very well organised tour visiting three vineyards with an excellent lunch

Beautiful wine and castles tour in Chianti

Laura_D, Jun 2024
We had an excellent Chianti Castles and wine tour with Georgia this week. We were very fortunate to only have 3 people on the tour which meant a much more personalised experience. We visited three different vineyards including the large estate of Castello di Brolio and the family wine producer La Lama. The latter included a delicious homemade intimate lunch, tasting and cellar tour (plus grappa and vin santo!) Georgia was extremely knowledgeable of the history, geography, food and wine of the area - we really could not have asked for more. We even purchased a few bottles to relive the memories at home. Grazie mille!

best day trip

Mary_B, Apr 2024
learned so much about the region and the history. the food and the wine were amazing as well. Loved out tour guide and would highly recommend!!

Great Tour

ROBERT_T, Oct 2023
Learning about the history of the region and quality designations of the wine from both the guide and vineyard representatives.

Highlight of my trip.

Natalia_M, Oct 2023
An intimate, fun excursion! We were staying in Siena and felt that it was the best way to see the beautiful Tuscan countryside and experience some excellent Chianti wines. We were right! Our tour guide was knowledgeable and polite, and had excellent relationships with the wineries we visited. Would do it again and would recommend to anyone looking to make new friends and learn about region!

Tuscan lifestyle with chanti tastings

Jane_W, Oct 2023
The guide Matteo was very knowledgeable and friendly!! The trip was very down to earth, small family run vineyards and lots of variety. Lots of photo opportunities!

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 winery...it 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.
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up to 24 hours before the experience starts (local time)

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