Free Cancellation

Key Details

City: Florence

Duration: Approx. 10 hrs

Start Time: 8:30 AM


  • 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. 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 from the outside, the location of the Palio, and wander its atmospheric streets
  • Enjoy a locally-sourced lunch with a 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
  • Relax knowing your two experts, a designated driver and local Italian guide have all the logistics for a perfect day in Italy

Tour Description

See the best of Siena with the comfort of a local expert

Our day starts in the center of Florence, meeting your expert guide, designated driver, and a small group (up to 14 other people). As we depart, you'll settle into a comfortable, air-conditioned luxury vehicle. But before you drive into the rolling hills of Tuscany, we'll make a stop at Florence's best panoramic viewpoint for photos. Our next stop will be eclectic, iconic Siena miraculously spared from bombing during WWII—making it a pristine medieval gem in the midst of the Tuscan region. Here we will walk the city center while your guide points out all the local culture and history including the famed Siena Cathedral as well as show you the location of the bi-annual Palio horserace.

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

Of course, no tour of Tuscany 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 arises, take a tour of an authentic farm, complete with spreading vineyards and full wine cellars. Then, it's time for lunch and this will not disappoint. What you eat will depend on the regional season. Tuscan cuisine is famously linked to produce, using only the freshest ingredients for the most hearty, delicious dishes. This is Italian food at its finest, all included in the price of your tour.

Explore a UNESCO World Heritage town - San Gimignano

With a full belly, we will move on to the little town of San Gimignano, so pretty and architecturally significant, it’s a UNESCO World Heritage Site. You'll enjoy a full tour of the city then have free time to shop for local Italian specialties or climb the city’s campanile for the other best view in Tuscany.

From start to finish the emphasis of our 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
  • Included
  • Expert English-speaking guide
  • Designated professional driver
  • Air-conditioned transport
  • Expertly guided walking tour of Siena
  • Expertly guided walking tour of San Gimignano
  • Gourmet lunch and wine tasting in Chianti
From $211
Free Cancellation


5-stars from over 1276 Customer Reviews


Mar 12, 2023

We had a phenomenal tour with Eleonora as our guide and Stefano as our driver. Siena was an unquestioned highlight. Our lunch and wine tasting was spectacular, and we very much enjoyed San Gimigniano as well. If you’re hesitating in any way - don’t! You’ll have a great time.

Important Information

Before you travel, please read our important notes about possible disruptions & site entrance requirements.