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Enchanting Italy Self Drive (Venice - Pisa - Florence - Assisi - Rome)

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9 Nights from $1,696*
* Sample price: priced within the past 7 days for a 9/9/2026 arrival, departing Boston BOS (MA), US. Choose departure city, cabin and dates.

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This 9 night sample itinerary price includes:

  • Flight into Venice and out of Rome
  • Hotel for 2 nights in Venice
  • Rental Car for 6 days
  • Hotel for 2 nights in Pisa
  • Hotel for 2 nights in Florence
  • Hotel for 1 night in Assisi
  • Hotel for 2 nights in Rome
  • Driving Time
    Venice - Pisa: 3 hrs. 30 mins. approx.
    Pisa - Florence: 1 hr. 30 mins. approx.
    Florence - Assisi: 2 hrs. 15 mins. approx.
    Assisi - Rome: 2 hrs. 30 mins. approx.

A perfect introduction to Italy!. Start in Venice (sumptuous palaces and romantic waterways), and after that, pick up your Rental Car and drive along the Tuscany, visiting Pisa (a city in Italy's Tuscany region best known for its iconic Leaning Tower) and Florence (home to many masterpieces of Renaissance Art and architecture) . After that, continue to Assisi (a hill town in central Italy’s Umbria region) and lastly, enjoy an unforgettable stay in Rome (famous for the Colosseum, Roman Forum, Vatican, and delicious food).

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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