Tuscany Day Trip from Florence with Chianti, Siena & San Gimignano

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.