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Get a true taste for the Tuscan countryside with this day trip to Siena, San Gimignano and a Chianti winery for dinner. Departing from Florence, venture first to the city of Siena for a guided tour through the Piazza del Campo, the site of the renowned Palio horse races, as well as a surprise food tasting. Afterward, wander the hilltown of San Gimignano before heading to a Chianti winery for a delicious 3-course dinner, complemented by fine local wine. Your trip is reserved to 16 people to keep the experience intimate.  


  • 8-hour Siena and San Gimignano tour with dinner in Chianti
  • Leave Florence and travel through the Tuscan countryside to Siena
  • Take a Siena walking tour around Piazza del Campo and the city’s picturesque streets
  • Make the most of some free time in the hill-town of San Gimignano
  • Visit a Chianti winery at sunset and savor a 3-course meal with wine, dessert wine and cookies
  • Small-group experience with a maximum of 16 people ensures personalized attention

Recent Photos of This Tour

What You Can Expect

Tuscany Small-Group Day Trip with Chianti Dinner: Siena and San Gimignano

Enjoy a surprise tasting in Siena!

Depart from central Florence and venture into the Tuscan countryside, a beautiful landscape marked by olive groves, green hills and cypress trees.

Arrive first in Siena, one of Tuscany’s crown jewels. Follow a local guide on a walking tour through the city, passing charming backstreets as well as Piazza del Campo, the celebrated main square that hosts the Palio horse races twice a year. Learn about Siena’s contrades, or districts, which each have individual legacies, traditions and anthems. Before departing, sample a surprise local specialty.

Continue to the hilltown of San Gimignano, known for its impressive towers. Relax with some time to roam the streets independently, popping into local shops or admiring the medieval architecture.  

Afterward, travel to a Chianti winery to soak up the sunset while eating dinner. Weather permitting, take a seat outdoors and feast on a 3-course meal of authentic Tuscan dishes with wine.

After a day of food, wine and sightseeing, you will be returned to central Florence.


Customer Reviews


5 star rating: Highly Recommended October 2016

Very nice tour to explore 2 of the best towns in Tuscany! The walking tour in Siena was really good with a local guide and you can hear about the contrade history and then have free time in San Giminiano followed by a dinner in Chianti which was super good! Big portions (appetizers, pasta, meat and dessert!) and lot of wine. Totally recommend if you have only one afternoon to explore the Tuscan countryside!

Alison E

5 star rating: Highly Recommended September 2016

The tour was fantastic, great drivers - really friendly and accommodating - even let me charge my cell phone on the way in the van, the guides at our stops were just awesome too, very informative and friendly. wouldn't hesitate to book another tour!!!

Casey A

5 star rating: Highly Recommended August 2016

Christian was a great guide and gave us good insight into the wine region of Tuscany. The history of Siena was provided through the experience of a local resident.

Raymond B

5 star rating: Highly Recommended August 2016

This was an excellent tour. We enjoyed the smaller groups. Christian and Matteop were our tour guides, and they made the tour very enjoyable. They had a real passion for what they were doing, and provided many interesting details along the way. The drive through Tuscany was beautiful. San Gimanano and Siena were beautiful cities. Each had a different feel. The best part was the evening Chianti Dinner. the setting was at a winery with a beautiful view for miles you could see Florence. We had a fun group of people. They served a complete dinner with wine, appetizers, multiple courses, and after dinner desert and drinks. Very beautiful and fun!.

Nicoletti D

5 star rating: Highly Recommended July 2016

It was a small group of 8 of us on this tour. We had a lovely dinner at a great restaurant with different wine pairings for every course. I also enjoyed exploring Siena and San Gimignano. Our tour guide, Christian, was also very helpful and knowledgeable. Highly recommend this trip!

Tom S

5 star rating: Highly Recommended July 2016

This was a FABULOUS trip. We were on an 11 day cruise with excursions every day, and this trip while we were staying in Florence after the cruise was a delight. Go and see Siena!

Miles P

5 star rating: Highly Recommended June 2016

Great, I would have no trouble recommending this to others.

DOVM Israel

5 star rating: Highly Recommended June 2016

Interestins. Very well organized. Wanderful gides. Beautiful places and good food and wine.

Jeanne R

5 star rating: Highly Recommended June 2016

This was an absolutely fantastic tour!!! We drove in comfort, super good tour guides and some time to explore on our own. Dinner and wine after a beautiful sunset. Would highly recommend!!!!

Kim B United States of ... 

5 star rating: Highly Recommended June 2016

Valerio, tour guide was terrific. Was very knowledgeable and went out of his way to show us things. Definitely recommend him as a guide and this trip. Siena was great and winery was unique experience.

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