Tuscany Day Trip: Siena, San Gimignano, Chianti & Pisa

From€475
9 hours
Florence, Italy

About this activity

Experience Tuscany's charm on a private day trip from Florence, visiting Siena, San Gimignano, Chianti, and Pisa, with guided tours and wine tasting.

Highlights

  • Explore Siena's historic center
  • Visit San Gimignano's medieval towers
  • Enjoy Chianti wine tasting
  • See Pisa's Leaning Tower
  • Discover Tuscan countryside landscapes

Full description

Discover the enchanting Tuscan countryside on a private day trip from Florence. Begin in Siena, renowned for its medieval architecture and the historic Piazza del Campo. Next, wander through San Gimignano, famous for its towering medieval structures. Enjoy a delightful wine tasting in the Chianti region, savoring the area's renowned wines. Conclude your journey in Pisa, marveling at the iconic Leaning Tower and the surrounding architectural wonders. This personalized tour offers a comprehensive glimpse into Tuscany's rich heritage and scenic beauty.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Siena, San Gimignano, and Pisa
  • Wine tasting in the Chianti region
  • Meals and personal expenses

Important information

Know before you book

  • Confirm the tour's availability on your preferred date.
  • Inform the operator of any dietary restrictions in advance.
  • Be aware that some sites may have entry fees not included in the tour price.

Know before you go

  • Wear comfortable walking shoes for cobblestone streets.
  • Bring a camera to capture picturesque landscapes.
  • Check the weather forecast and dress accordingly.

Cancellation policy

Free cancellation up to 1 days before the activity starts

For a full refund, cancel at least 24 hours before the scheduled departure time.

Accessibility

  • Stroller Accessible
  • Easy Public Transport
  • Infant Seats Available

Good to know

  • We can accommodate people using a foldable wheelchair

Traveler reviews

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Beat our expectations!

Lorenzo was an incredible tour guide and made the trip that much better by sharing all of his knowledge on Tuscany with us. Serge did a great job getting us around safely with minimal wait time on pick up. Highly recommend them!

bettygM6459AMOct 25, 2026TRIPADVISOR

Private driver is great way to go

Great driver- Roberto. Very informative and knowledgeable about the areas. Gave suggestions on areas for great pics. Very polite and patient. Suggested a very good restaurant for lunch which was great. Smooth ride.

562adamsaOct 16, 2026TRIPADVISOR

The Best

Paolo was a wonderful guide: smart, helpful and caring. A great itinerary and recommendations. Worth every penny.

Peter_POct 13, 2026VIATOR

A private view of Tuscany....a lifetime memory

My experience working with Carrie at Prestige Rent to create a personalized experience was awesome....she is a true professional and a joy to have worked with. Our driver Donatello was knowledgeable of this region and helped made this tour a memory of a lifetime. I would highly recommend this tour if you want to see the true Tuscany region!

Curtis_VOct 5, 2026VIATOR

Siena tour

Alessia was outstanding - very knowledgeable and organized. All in all a very good tour and day !

Explorer54747245842Oct 4, 2026TRIPADVISOR

Additional information

We can accommodate people using a foldable wheelchair