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Rail to Road: Rome - Florence - Chianti - Venice

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11 Nights from $1,877*
* Sample price: priced within the past 7 days for a 5/26/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 11 night sample itinerary includes:

  • Flight into Rome and out of Venice
  • Hotel for 3 nights in Rome
  • Train from Rome to Florence
  • Hotel for 2 nights in Florence
  • Rental Car for 4 days
  • Hotel for 3 nights in Chianti Wine Region
  • Hotel for 1 night in Florence
  • Train from Florence to Venice
  • Hotel for 2 nights in Venice
  • Driving Time
    Florence - Chianti Wine Region 1 hr. / 1hr. 30 mins. approx.
    Chianti Wine Region - Florence: 1 hr. / 1hr. 30 mins. approx.

Charming Italy Countryside!. Spend a few days visiting Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food) after that, take a train to enjoy Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). From there, pick up the Rental Car, for an enchanting visit to the Chianti Wine Region (beautiful and famous region of Tuscany with best wineries). Drive back Florence to drop the car, and after that, continue by train to ultra-romantic Venice (set on gorgeous canals, intimate Gondola rides under sculpted bridges).

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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