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Tuscan Highlights Self Drive (Florence - Siena - San Gimignano)

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7 Nights from $1,385*
* Sample price: priced within the past 7 days for a 5/21/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 7 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 2 nights in Florence
  • Rental Car for 6 days
  • Hotel for 2 nights in Siena
  • Hotel for 2 nights in San Gimignano
  • Hotel for 1 night in Florence
  • Driving Time
    Florence - Siena: 1 hr. 10 mins. approx.
    Siena - San Gimignano: 1 hr. approx.
    San Gimignano - Florence: 1 hr. 15 mins. approx.

A unique trip to Italy's Tuscany Region by car! . Discover Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture) and from there, with Rental Car, main cities in Tuscany, like Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio horse race in Piazza del Campo) and San Gimignano (famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses). Drive back to Florence to drop off the car and finisht this trip with one last night stay.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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