4.5 star rating: Recommended 13 Reviews

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

From USD $ 166.27

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Tour code: 5049CHIANTI007


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