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Tour code: 5049CHIANTI007
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

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.


Sample Menu:
First course:
  • Bruschetta with Tuscan olive oil
Second course:
  • Platter of cheese and locally cured cold meat
Third course (choice of one):
  • Tuscan ribollita (country-style soup made with bread, cannellini beans and vegetables)
  • Lasagne
Follow your third course with a glass of vinsanto (local dessert wine) and cantucci (traditional Tuscan cookies)

Customer Reviews

Vicky L

5 star rating: Highly Recommended April 2016

This tour was amazing!

nancy s

5 star rating: Highly Recommended November 2015

A delightful way to get out of the busyness of Florence and see a lot in a day! The tour of Siena was great, although it would have been nice to go inside the duomo. San Gimignano is a great little town. The dinner was absolutely wonderful. And our tour guide, Elizieo, was very kind and full of interesting information about the area, history, etc.

Mary M

5 star rating: Highly Recommended September 2015

This tour was lovely! Beautiful country and delicious food. Siena was amazing and our guide was knowledgeable about the history of the city. The day went by fast and I would highly recommend this tour.

George M

5 star rating: Highly Recommended September 2015

Excellent way to explore these beautiful places in Tuscany. Definitely can enjoy a personal experience with the small tour. Particularly impressed with our walking tour and guide in Sienna - 'Benni's' passion for her city was evident. We even saw a beautiful sunset over the hills prior to dinner.

Stephen Z

5 star rating: Highly Recommended July 2015

A lot of fun! Giacomo was great. We would definitely do it again. And bring your appetite there is a lot of food and wine!

Fabian P

5 star rating: Highly Recommended May 2015

I love the guides, they were fun and very funny, it was sad that the day we went, it was rainy! this is a small private tour to bring you to these awesome places for a very reasonable price! I would Recommend you if for this guide if you are in Florence and want to visit Siena just for a day trip. Since it was raining, the tour sent us to our hotel which was very nice of him to go the extra mile for his customers!
I did this for my honeymoon and my wife and I are happy!

Leticia C

5 star rating: Highly Recommended May 2015

Not only were the drivers who accompanied us - Eliseu and Giacomo - the sweetest people ever, but the guide from Siena was clearly proud of her city. I would have liked a little more time in San Gimignano, and to have known it was a place so cute for shopping, though. The Chianti Dinner: absolutely delicious.

Jonathan C

5 star rating: Highly Recommended November 2014

Nice respite from the crowds in Florence. The two towns are great, and we were able to tailor our time there to suit the varied desires of the 8 people in our group. Bad rain hampered or time at the Choant winery, and I would have liked a more educational experience there. But very nice.

Kristi A

5 star rating: Highly Recommended September 2014

Visiting Siena was the highlight of my trip to Italy. It was so neat to learn about the city and its traditions. San Gimignano was very cool to see too. I will forewarn you that the ride in the van is bumpy, especially if you ride in the back.

Michael B

5 star rating: Highly Recommended September 2014

An Excellent trip to a lovely city, a charming young lady vintner for our wine tasting who joined in the humour that abounded in our small group trip: Ciao Bella

From USD $ 171.21

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