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Rail to Road: Milan - Bologna and San Marino

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9 Nights from $1,459*
* Sample price: priced within the past 7 days for a 5/20/2026 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 Milan and out of Bologna
  • Hotel for 3 nights in Milan
  • Train from Milan to Bologna
  • Hotel for 2 nights in Bologna
  • Rental Car for 4 days
  • Hotel for 3 nights in San Marino
  • Hotel for 1 night in Bologna
  • Driving Time
    Bologna - San Marino: 1 hr. 40 mins. approx.
    San Marino - Bologna: 1 hr. 40 mins. approx.

An unforgettable holiday in Italy and San Marino. Begin your vacation with a visit to Milan (a fashion and shopping capital) and then, catch a train to Bologna (a thriving university town and architectural gem). Finally, pick up your Rental Car for a scenic drive to San Marino (a mountainous microstate located within Italy and one of the world's oldest republics). Drive back to Bologna for a last night stay before returning home.

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
Live phone and chat support

Italy
San Marino

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