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4.5 star rating: Recommended 22 Reviews

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  • Location:Florence, Italy
  • Duration:9 hours (approx.)

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

Head to the Tuscan hills on a day trip from Florence to visit Siena, San Gimignano and, finally, a Chianti winery for dinner! Journey through stretches of glorious Tuscan countryside, and discover Siena’s charms and history on a walking tour. Explore Piazza del Campo, meander around the quieter backstreets and try a local food specialty before visiting the nearby hilltown of San Gimignano. As the day winds to an end, watch the sun set from a Chianti winery while feasting on a 3-course dinner with wine, dessert wine and cookies.

Numbers are limited to 16 on this small-group tour, ensuring a personalized experience.


  • 9-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!

Board your air-conditioned minibus in central Florence, and travel into the beautiful Tuscan countryside that surrounds the city. Rolling green hills, punctuated by cypress tree–lined lanes and olive groves, characterize the gorgeous landscape that stretches out in front of you.

Soak up the scenery as you relax on the journey to Siena, Tuscany’s second-largest city. In ancient times, the city competed with Florence for power, wealth and artistic beauty; today the city holds a reputation as an urban gem in Tuscany’s crown. Enjoy a walking tour, seeing Piazza del Campo — site of the annual Palio horse race — as well as the enchanting backstreets that many visitors fail to discover. Learn about Siena’s history and hear tales of the contrades for which Siena is famous. Loosely translated as districts, the contrades have individual legacies of traditions and emotions, and each boasts their own flag and anthems.

Before leaving Siena, enjoy a surprise food tasting of a traditional local specialty. Then, reboard your minibus and travel to San Gimignano, another beautiful Tuscan hilltop town. Famed for its medieval ‘skyscrapers’ and twisting stone streets, the charming town is the ideal place to wind down with some free time and explore.

From San Gimignano, continue through the countryside and stop at a Chianti winery in time to see the sun go down over dinner. If the weather is good, take a seat at an outdoor table or alternatively, eat inside and gaze at the Tuscan sun setting over the hills while savoring a meal of traditional Tuscan specialties with wine.

When your meal is finished, travel with your guide back to the start point in central Florence where your evening experience ends.

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

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.

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.

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.

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!

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!

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.

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.

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.

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

5 star rating: Highly Recommended August 2014

We loved our guide's presentation and knowledge of her home city of Siena! The wine dinner was good, but a little bit rushed. Would liked to have more time between wines and dinner courses. The 30 year balsamic vinegar was great too! A lovely day ending with a gorgeous view of Firenze at night!

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Tour code: 5049CHIANTI007


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