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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 Briolo, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Meleto. 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
  • Sample Black Rooster Chianti Classico wine at Castello di Meleto
  • Small-group tour (maximum eight people) provides a unique and intimate experience

Recent Photos of This Tour

What You Can Expect

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

Castello di Meleto, Chianti

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 Chastello di Brilio, 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 Meleto, an 15th-century fortress replete with ancient fortifications and a distinctive cylindrical tower. Absorb surrounding panoramas of sun-kissed vineyards as you tour the famous winery and sample a glass of signature wine, Black Rooster Chianti Classico.

Next, prepare to appease your appetite with a delectable Tuscan lunch at a local farm; feast upon platters of locally sourced food and then head to a quaint medieval village to spend some leisurely free time exploring. 

Conclude your tour at another Chianti winery to enrich your knowledge of production methods and the rich Chianti culture. Descend to the cellars, stroll the pretty gardens and then return to your vehicle for the relaxing ride back to Siena.  

Customer Reviews

Patricia B

5 star rating: Highly Recommended October 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!

Neil G

5 star rating: Highly Recommended September 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!

Katrin W

5 star rating: Highly Recommended July 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.

Scott C

5 star rating: Highly Recommended September 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!

Stephen A

5 star rating: Highly Recommended September 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

Sandie T

5 star rating: Highly Recommended October 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.

Robert G

5 star rating: Highly Recommended October 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!

Rosemary A

5 star rating: Highly Recommended June 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!

Ian H Australia

5 star rating: Highly Recommended November 2012

Absolutely excellent. Milo was a great tour leader. The wineries we visited were great. I would highly recommend the tour.

Olin S

5 star rating: Highly Recommended October 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!

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