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.

Please note that this description is an example and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience.

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
1458 Customer Reviews
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Jul 21, 2024

Annette was a wonderful tour house, very knowledgeable and friendly. We had an amazing day, absolutely loved the winery lunch. Thank you Walks of Italy


May 28, 2024

Elana was great!! Locations were great,


Apr 29, 2024

We picked a Walks tour because we heard you are paired with local guides. This was our experience with Eriza who is from Siena. Our day long trip was the perfect amount of touring in Siena and San Gimignano free time, one Chianti winery run by a small family with a fabulous fresh cooked lunch. The small group of 8 people was awesome and really allowed for a special experience for our first trip to the Tuscany region. Can't wait to come back and take another tour with Walks!


Apr 23, 2024

Great tour, thank you Nebo. Very appreciated the beautiful cities and views together with very nice food and interesting wine tasting in an authentic Tuscan spot.


Apr 18, 2024

One of the best tours we have done in Italy. Our tour guide, Matt, spoke excellent English, was charming and extremely knowledgeable. The lunch and wine tasting was of a high standard. Transport in luxury vans was very comfortable. Highly recommend this tour.

Know before you book

From $217
Free Cancellation