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Head north from Sienna to fabled Chianti on this small-group tour. Explore the region known as Florentine Chianti, stopping to take in the charming small towns of Castellina in Chianti and Greve in Chianti. Stroll the streets, meeting some of the region’s charming residents and, of course, partake in some locally made wine during a visit to two wineries. Indulge in a lunch of Tuscan delights. This small-group tour of Florentine Chianti is limited to just eight participants, ensuring you’ll get molto attention from the guide. 


  • Small-group day trip to the Florentine Chianti region from Siena
  • Visit the magnificent Chianti towns of Castellina and Greve
  • Take a stroll through vineyards and olive groves with your expert guide
  • Enjoy a delicious Tuscan lunch and a wine tasting of Black Rooster Chianti Classico (included)
  • Small-group tour with a maximum of eight passengers ensures a more intimate experience

Recent Photos of This Tour

What You Can Expect

Small-Group Day Trip to Castellina and Greve in Chianti from Siena

Small-Group Day Trip to Castellina and Greve in Chianti from Siena

Meet your guide in the morning and hop in the comfortable air-conditioned minivan for the short ride to Chianti. Gawk at the fabled Tuscan countryside as the rolling grape-vine blanketed landscape, the hills crowned by rustic villas and the tiny ancient villages all unveil themselves before your eyes. 

Stop in the walled medieval town of Castellina in Chianti for a short stroll around its narrow cobbled lanes and see the imposing Castellina Castle, an imposing 15th-century fortress, that was built by the order of Lorenzo il Magnifico, from the legendary Medici of Florence. 

Hop back in the minivan for the brief journey to the next stop: Greve in Chianti. In the village, take some free time to explore on your own. Perhaps linger in the triangle-shaped piazza or follow the trail of the legendary sailor Verrazzano. Pop into small shops and browse the goods for sale at the outdoor market stalls. 

After some time in Greve, ride to Montefioralle, a small town whose claim to fame is that it is reportedly the hometown of the famed Amerigo Vespucci, the cartographer whose first name became the name of two continents: America. Take a stroll around the town and don’t pass up drinking in the incredible views of the Tuscan countryside. 

If all that sightseeing has built up a thirst and hunger, stop by a nearby family-run winery next. Sample some locally made wine, including the famous Chianti Classico, and indulge in a lunch of Tuscan deliciousness, from prosciutto to local cheese. Later, visit a second winery: descend into the cellar to sample some more local vino and learn from the winemaker about the particular characteristics of wine from the area. 

Before heading back to Siena, stop by the Abbey of Passignano, a gorgeous 11th-century structure that is surrounded by classic Tuscan nature and landscapes. 

Customer Reviews


5 star rating: Highly Recommended October 2014

This is definetely a tour worth doing while visiting the Chianti region! This was the highlight of my weekend trip to Siena. We were escorted to the beautfil village of Castellina by private van, after listening to an interesting take on Chinati wine thanks to our guide. After spending some free time in the village and seeing the main attraction of the medieval tunnel, we departed for Greve where a weekend market was taking place. The tour guide stopped at a beautiful little village and let us take photos. The highlight of the day was eating a delicious home-cooked Italian lunch in a little farm and winery. The Italian couple were amazing hosts and were so passionate about their wine business and the Chianti region. They made the lunch so enjoyable, thank you so much! We then went to a larger winery where we were able to watch part of the harvesting process occur. This was exciting and fascinating to watch. We enjoyed another wine tasting here. This is a tour definetely worth doing when you stay in Siena, but be mindful it's a busy day as you do so much! Thank you for an excellent day out!

merryberry China

5 star rating: Highly Recommended October 2014

It was a wonderful day in the Chianti region. Both Castellina and Greve in Chianti are beautiful towns not to be missed. The farm where we had lunch gave you a true and sincere experience of Italian family. I'm surprised that this tour is yet to be rated on Viator.

Roberta H

5 star rating: Highly Recommended July 2013

We had an outstanding time. Great tour, outstanding guide, and absolutely wonderful day. Felt as if we were part of the Tuscany. . Loved the lunch at the winery. Was a wonderful experience.

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