Approx. 9 hrs
8:30 AM
Max 14


  • World-famous for its hillside towns, sweeping views, cuisine, and wine, there are endless reasons to visit Tuscany. Experience all of these in the most authentic, relaxed way possible on this meticulously planned Tuscany day trip from Florence. Take the hassle out of your visit so you can sit back, relax, and enjoy a glass of wine (or two).
  • Travel through Tuscany to Siena, Chianti, and San Gimignano in a small luxury vehicle with no more than 14 others.
  • Stroll the beautiful medieval town of Siena, see its cathedral and the location of the Palio, and wander its atmospheric streets.
  • Sit down for a relaxing lunch and wine tasting at an authentic Chianti farmhouse and vineyard.
  • Explore one of Tuscany’s gems—the town of San Gimignano, a UNESCO World Heritage site—with a knowledgeable guide.
  • Relax knowing that your two experts, a professional driver and local guide, have all the logistics handled for a perfect day in Italy.

Tour description

Discover three stunning destinations on a perfectly planned Tuscany day trip from Florence.

In just one day, you'll see, taste, and experience the best of Tuscany, complete with a homemade locally sourced lunch and expert-led wine tasting at a family-run farm in Chianti. We'll whisk you away to Siena and San Gimignano, two of the most stunning towns in Tuscany, helping you experience as much of this storied region as possible without you having to worry about the logistics. With a knowledgeable guide to lead the way as well as an experienced driver to get you from place to place, we've got all the details handled for an unforgettable Tuscany day trip from Florence.

See the best of Siena with the guidance of an expert in all things Tuscany.

Our day trip to Tuscany starts in the center of Florence, where you'll meet your expert guide, dedicated driver, and small group before boarding a comfortable, air-conditioned luxury vehicle. But before we set off into the rolling hills of Tuscany, we'll make a stop at Florence's best panoramic viewpoint for photos.

Your next stop will be eclectic, iconic Siena, which was miraculously spared from bombing during WWII—making it a pristine medieval gem in the midst of the Tuscan region. Stroll through the historic streets of the city center while your guide points out the most notable landmarks, including the famed Siena Cathedral and the location of the biannual Palio horserace.

Enjoy a gourmet lunch paired with impeccable wine on an authentic Chianti farm.

Of course, no Tuscany day trip from Florence is complete without a visit to the wine region! Chianti is a postcard-perfect area full of rolling hills and quaint farmhouses. As the lunch hour draws near, you'll take a tour of a family-run farm and winery, complete with sprawling vineyards and full wine cellars.

Time for lunch—and trust us, it won't disappoint. The menu varies seasonally, as Tuscan cuisine is famously linked to produce and uses only the freshest ingredients for the heartiest, most delicious dishes. Paired with a selection of the vineyard's very own wines, this is Italian food at its finest—and it's all included in the price of your tour.

Explore the UNESCO World Heritage town of San Gimignano.

With full bellies, we'll move on to the picturesque town of San Gimignano—so visually stunning and architecturally significant that it’s a UNESCO World Heritage Site. You'll enjoy a full tour of the town, then have a bit of free time to shop for local Italian specialties or climb the city’s campanile for one of the best views in Tuscany.

From start to finish, the emphasis of our Tuscany day trip from Florence is on indulgence. Indulge in stunning scenery, delicious wines, and lazy strolls on our all-inclusive Tuscan adventure. We’ve taken care of all the details so all you have to worry about is how much Chianti wine you can fit in your suitcase.

Sites visited

  • Piazzale Michelangelo
  • Tuscany Region
  • Siena
  • Siena Cathedral (exterior)
  • Piazza del Campo (Siena)
  • Chianti farmhouse & vineyard
  • San Gimignano


Verified guest reviews

4.7 / 5
1422 Customer Reviews
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Jan 26, 2024

100% recommend! Our guide was so welcoming and enjoyable to be around. Booking a day trip with Walks made everything so seamless and allowed us to enjoy our experience even more. Don't hesitate to book!


Jan 09, 2024

The driver and the tour guide are absolutely amazing thank you to our tour guide helena. The winery was really nice clean and beautiful. The family who owned it were all there to greet you and serve you food n wine. We went and toured 2 small incredible towns. Our guide was incredibly knowledgeable as well as so sweet and kind. She got to know us all and find out what we wanted to see and do and acomidated us all. Value - worth the cost plus more. You won't be disappointed i promise.


Oct 24, 2023

Stephanie was excellent! Tour was perfect in terms of amount of time spent in each place, visit and lunch to family owned winery was excellent!


Oct 20, 2023

The tour was excellent! Interesting places. Special thanks to the driver! He was so calm and told us some interesting details while driving. Thank you!


Oct 18, 2023

Sandra was a GREAT guide, and the sites visited were fantastic!

Know before you book

From $172
Free Cancellation