5 star rating: Highly Recommended 10 Reviews

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  • Location:Siena, Italy
  • Duration:8 hours (approx.)

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

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine, and explore Castello di Meleto. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan farm and tour the region’s best wineries.

Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide.


  • 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

Leave Siena aboard a luxury minivan and head east into the heart of Italy’s picturesque Chianti region to start your Chianti wine-tasting and castles trip. Passing through the captivating countryside, you'll see the cypress trees and olive groves that typify this beautiful part of Tuscany. Soon enough, you'll notice impressive castles, fortified farm houses and towers that bear testimony to turbulent wars between the once opposing republics of Siena and Florence.

Perched high on a forested hill sits the enchanting Castello di Brolio -- your first Chianti castle visit of the day. Learn about its importance during medieval battles, and about the fascinating Ricasoli family who have owned the castle since the 11th century. With your friendly and knowledgeable guide, explore the Castello di Brolio vineyards where the world-famous red Chianti wine is said to have originated. Then, enjoy a photo opportunity amid the gorgeous surroundings.

Continue to Castello di Meleto, another impressive Chianti castle with 15th-century fortifications and a distinctive cylindrical tower. Surrounded by sun-kissed fields, the castle is now a famous winery, boasting large vineyards and a wine-tasting room. With your guide, tour the castle grounds before savoring a glass of Black Rooster Chianti Classico -- the winery's most prestigious red wine.

Once you’ve worked up an appetite, head to a traditional Tuscan farm for lunch and enjoy platters of locally produced food and fine wines. After this delicious feast, continue to one of the countryside’s many quaint medieval villages and spend time exploring at leisure. Your guide will happily recommend local coffee bars or interesting sights for you to see.

The last stop of the day is at another Chianti winery, where you'll meet the local producer and hear about the lifestyle of the charismatic Chianti folk. Visit the cellars and gardens before enjoying a relaxing ride back to Siena.

Customer Reviews

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!

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

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.

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!

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

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.

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!

5 star rating: Highly Recommended July 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!

5 star rating: Highly Recommended 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.

4 star rating: Recommended November 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.

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