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San Marino - Siena - Florence (Self Drive)

9 Nights from $1,368*
* Sample price: priced within the past 7 days for a 5/15/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 9 night sample itinerary includes:

  • Flight into Bologna and out of Florence
  • Rental Car for 7 days.Pick Up: Bologna Airport/Drop Off: Florence Downtown
  • Hotel for 3 nights in San Marino
  • Hotel for 3 nights in Siena
  • Hotel for 3 nights in Florence
  • Driving Time
    Bologna Airport - San Marino: 1 hr. 35 mins. approx.
    San Marino - Siena: 3 hrs. approx.
    Siena - Florence: 1 hr. 10 mins. approx.

San Marino and Italian Tuscany!. Behold the beautiful natural landscape as you drive to San Marino (a mountainous microstate located within Italy and one of the world's oldest republics), then continue to medieval Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo) and finally the artistic city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture).

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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San Marino
Italy

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