5 star rating: Highly Recommended 3 Reviews

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

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

This small-group tour from Siena takes you to Tuscany’s northern Chianti region, known as the Florentine Chianti, where you’ll visit the pretty villages of Castellina and Greve (officially known as Castellina in Chianti and Greve in Chianti). During this full-day trip, see breathtaking landscapes, enjoy a traditional lunch and visit two wineries with your expert guide. Meet the area's famously welcoming inhabitants and get a taste for life in the Florentine Chianti!

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

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What You Can Expect

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

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

Leave Siena early in a luxury minivan with your guide, and set off to the Chianti hills, enjoying views of beautiful forests, rows of vineyards and pretty medieval hamlets. Your first stop is the walled village of Castellina in Chianti, where you'll explore the town and its covered medieval walkway with your guide. See the fascinating Castle of Castellina, which dates to the 15th century and was built by the order of Lorenzo il Manifico, a popular Florentine statesman in medieval times.

Next, head to the beautiful town of Greve in Chianti, famous for its triangular-shaped piazza and for being the home of famous sailor Verrazzano. Have leisure time here to sample wines (additional cost) or visit the local boutiques and market stalls.

From Greve, you'll take a short drive over to Montefioralle, a village that claims to be the birthplace of Amerigo Verpucci, the famous cartographer who gave his name to the Americas. Enjoy a walk along Montefioralle’s cobbled streets and take in the breathtaking views.

Just outside of this beautiful village is a family-run winery, where you'll enjoy a delicious Tuscan lunch, consisting of cured meats, home-grown vegetables and cheeses, and enjoy a wine tasting of the famous Black Rooster Chianti Classico. While you eat and drink, learn from your friendly guide about the region’s customs and traditions. Then visit another, larger winery, where you’ll be guided through the process of wine production and visit the wine cellars. Hear more about Chianti’s famous red wines, including how they are made and the differences in flavor of the various blends and grapes.

Your last stop before returning to Siena is the beautiful Abbey of Passignano, where you’ll admire the glorious landscapes of the surrounding countryside. The abbey, whose existence has been documented from the beginning of the 11th century, was once one of the most powerful castles of the Val di Pesa.

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!

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.

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.

From USD $ 145.56

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Tour code: 5493FLORENTINE


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