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

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Siena, Italy

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Free Cancellation
up to 24 hours in advance
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Safety measures
icon8 hours  (Approx.)
Mobile ticket
iconOffered in: English and 1 more
Good for avoiding crowds


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
Have questions?
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Professional guide
Wine tasting
Air-conditioned vehicle
Hotel pickup and drop-off
Entrance to Castello di Brolio

Departure Point

Piazza S. Domenico, 53100 Siena SI, Italy

Departure Time

9:30 AM

Return Details

Returns to original departure point
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.
Stop At:  
Castello di Brolio
visit the gardens of Castello di Brolio, learn about its history and enjoy the stunning views overlooking the nighbouring valleys and hills before tasting their fantastic wines
Duration: 50 minutes
Admission Ticket Included
Stop At:  
Castello di Vertine
visit the beautiful hamlet of Vertine that was once a fortified medieval village
Duration: 20 minutes
Admission Ticket Free
Stop At:  
Radda in Chianti
Medieval town with great architecture and shops, leisure time to browse
Duration: 40 minutes
Admission Ticket Free
  • 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
  • OPERATED BY Tuscan Escapes by Papilio

For a full refund, cancel at least 24 hours in advance of the start date of the experience.

  • 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.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on face masks and attendee health during Small-Group Chianti Wine-Tasting and Castles Trip from Siena?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
See all safety measures taken by Small-Group Chianti Wine-Tasting and Castles Trip from Siena.
What is the policy on sanitization during Small-Group Chianti Wine-Tasting and Castles Trip from Siena?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by Small-Group Chianti Wine-Tasting and Castles Trip from Siena.
What is the social distancing policy during Small-Group Chianti Wine-Tasting and Castles Trip from Siena?
A:The policy on social distancing is:

  • Social distancing enforced throughout experience
See all safety measures taken by Small-Group Chianti Wine-Tasting and Castles Trip from Siena.
What measures are being taken to ensure staff health & safety during Small-Group Chianti Wine-Tasting and Castles Trip from Siena?
A:The policies on staff health & safety are:

  • Guides required to regularly wash hands
  • Regular temperature checks for staff
  • Paid stay-at-home policy for staff with symptoms
See all safety measures taken by Small-Group Chianti Wine-Tasting and Castles Trip from Siena.
What is the maximum group size during Small-Group Chianti Wine-Tasting and Castles Trip from Siena?
A:This activity will have a maximum of 8 travelers.

See all safety measures taken by Small-Group Chianti Wine-Tasting and Castles Trip from Siena.

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35 Reviews
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Reviews by Viator travelers

Showing 1-10 of 35 reviews
Tuscany vineyards
, 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!!
, 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!
, 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...
, 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!

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