• Location: Florence, Italy
  • Duration: 8 hours (approx.)
From USD $ 236.11 View price calendar

Low Price Guarantee

Explore the world-class Chianti wine region on a day trip from Florence. Led by an expert guide, stop in Siena for sightseeing, a light lunch and wine tasting. Learn how regional wines are produced at a prominent Chianti winery. Then, discover the hill town of San Gimignano, famous for its medieval architecture and incredible vistas. Enjoy stops at two more wine villages to sample the local blends before heading back to Florence. Numbers are limited to eight people on this tour to ensure an intimate experience.


  • Small group day trip from Florence to Chianti region and hill towns of Tuscany
  • Experience Chianti's natural beauty, gorgeous scenery and small-village way of life
  • Visit the medieval towns of Siena and San Gimignano
  • Explore the hill town of Siena and enjoy a light lunch
  • Maximum 8-person groups ensure highly personalized experience

What You Can Expect

Siena, San Gimignano and Chianti Wine Region Small Group Day Trip from Florence

Chianti Wine Region Small Group Day Trip from Florence

Your tour will begin in central Florence, where you’ll join your guide and hop aboard your coach. Head first to the Tuscan hill town of Siena, known for its Palio di Siena, a horse race held twice a year in the main square. Hear insightful commentary from your guide as you explore the Piazza del Campo and surrounding streets.

Continue to a popular winery in the Chianti area, where you’ll learn about the production of regional wines. Sip on three, authentic Chianti blends, including the famous vin santo, complemented by a light lunch of cold cuts, cheeses and bruschetta.

After your Tuscan lunch and wine tasting, head to the medieval town of San Gimignano. Take a leisurely walk with your guide to admire the Gothic and Romanesque architecture, and enjoy stunning vistas from the prominent landmark of the Torre Grossa.

Make your way back to Florence along the scenic route through Chianti, stopping in the villages of Monteriggioni. Sip on more flavorful local blends before returning to your original departure point in Florence.

PLEASE NOTE: The order of the places visited  might change.

Customer Reviews

anthony d

5 star rating: Highly Recommended April 2018

Our guide Yaris was the best. He was so knowledgeable and gave us the experience of our lives. My 16 year old daughter thought this was the highlight of our 10 day trip.

rschantz United States of ... 

5 star rating: Highly Recommended October 2017

I had an excellent experience with this tour, and would recommend it without reservation. We were a small group with our guide/driver Giuliano and our guide in Siena, Adele. We rode in a clean mini-van and were not crowded at all. Giuliano spoke excellent English and was an expert with wines - from grape growing, wine making, aging, bottling, distribution and even to grappa. He was able to answer all the questions in a very clear, very pleasant and helpful way. Our guide in Siena, Adele, is Sienese, and we learned a lot about the various churches and saints as well as the various contrade in Siena that compete in the famous Palio. We stopped at a family-run farm just outside of San Gimignano, where we had the various wines from the family's properties in San Gimignano and in Siena. The wines were excellent. All of the family were helping - we had Pietro, one of the sons, to help us. He explained everything in great detail, very clearly, and very thoughtfully. It was a pleasure to meet him and to taste his family's wines. We were served lunch, as part of the wine tasting. Because we were a small group, we were able to also see Monteriggioni just outside of Siena, the walled village built by the Sienese as a outpost against the Florentines in the 1200's. We also drove through Chianti on our way back and saw the Abbey of Badia a Passignano, as well as the little medieval town of Montefioralle. A very memorable trip!


5 star rating: Highly Recommended June 2017

This was one of the best days we had in Italy. An absolute MUST. The guide/driver was so friendly and knowledgeable. The vineyard was remarkable.

Cheryl Y

5 star rating: Highly Recommended May 2017

This trip was amazing. It was great having a small group. You didn't feel lost in the crowd. Our driver/main guide was very charming and fun. Siena and San Gimignano were so beautiful and interesting. Our guide in Siena was lovely and very knowledgeable. She is from Siena and that made it even more fun. The vineyard we visited was beautiful and the tour was very informative. More importantly, the wine was wonderful and the lunch served was excellent. Be prepared to walk a lot and keep in mind that you will be doing a lot of climbing. The cities are built on hills so you have a great deal of climbing and steep inclines but the pace was slow so not too difficult. Wear good walking shoes. Also, you will be visiting a lovely church, so no shorts and no bare shoulders ladies. Carry a light shawl or scarf with you to put over your shoulders.


5 star rating: Highly Recommended October 2016

Our driver/guide was knowledgeable, interesting and friendly. Our local guide in Siena showed us a personal side of the city, walking through neighborhood and learning the history of this beautiful city. Our lunch and wine tour in Chianti was beautiful and delicious! Great tour!

Chuck United States of ... 

5 star rating: Highly Recommended August 2016

A great tour. Our tour guide, Jakamo, knew the areas very well and was a really valuable part of the tour. Each town was unique and really gave us a good sense of Italy that we couldn't have gotten in Florence or as part of a large group, and the winery visit was a nice addition. Definitely a fun and interesting day.

Amily H

5 star rating: Highly Recommended July 2016

Great history lesson, and vineyard experience. If your looking for more tasting, I'd recommend the all day wine tour by viator.

David R

5 star rating: Highly Recommended June 2016

Great experince

Richard S

5 star rating: Highly Recommended May 2016

Our tour guide driver Jonathan ,was a wealth of information ,pleasant, and very accommodating, a great day with him. Elizabeth ,the tour guide in sienna was also a wealth of information and showed us the nooks and crannies of Siena, what a pleasure .

Richard S

5 star rating: Highly Recommended May 2016

This trip was absolutely fantastic! We enjoyed each of the 4 stops but especially liked the stop in Siena with a walking tour and tour guide. Giacomo did a great job driving us around and I would certainly recommend this trip. We stopped at one winery with a short tour, several tastings and a lunch of cheese, meats and bread.

Viator uses cookies to improve your experience on our website. Learn more about how we use cookies and how to change your cookie settings | Close message