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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

Recent Photos of This Tour

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 and Castellina in Chianti. Sip on more flavorful local blends before returning to your original departure point in Florence.

Customer Reviews


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.

Joseph S

5 star rating: Highly Recommended September 2015

Beautiful, breathtaking, countryside!! The growers of the two vineyards we visited were very hospitable. Our guide Giacomo was quite knowledgeable, a gem.

Edward K

5 star rating: Highly Recommended June 2015

Great tour, wonderful friendly guide. Highly recommended day trip from Florence

Anne N

5 star rating: Highly Recommended June 2015

Good bus, Jacamo an excellent driver we saw the countryside and had frequent stops. Not suitable because of timings to take photos but most enjoyable wine tastings. No lunch available at a trattoria but purchased at the first vineyard meat and cheese platter for 15 e each. Very informative tasting at our second stop but unfortunately due to other visitors there was no room for us to sit outside for our tastings which would have been nice. Overall very nice to get out of the city and see the countryside.


5 star rating: Highly Recommended October 2014

Fantastic tour. The scenery was amazing and the wineries and towns we visited were just perfect. The van was very comfortable for the drive and the length of the tour was just right. Our guide Fabrizio (forgive me if I've spelled his name wrong) was the best. He went out of his way to pick up other people on the tour who were late, took us to a few spots that weren't necessarily part of the tour (like stopping on the hill above Florence for pics, etc). One of the people on the tour left her phone behind at a previous stop, and Fabrizio called back, arranged to have someone he knew look for it and then got it back later in the day and was going to deliver it to the hotel of the person who lost it. Top notch service for sure.

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