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Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)

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10 Nights from $2,104*
* Sample price: priced within the past 7 days for a 10/9/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 10 night sample itinerary price includes:

  • Flight into Pisa and out of Rome
  • Rental Car for 9 days
  • Hotel for 2 nights in Pisa
  • Hotel for 2 nights in San Gimignano
  • Hotel for 2 nights in Siena
  • Hotel for 2 nights in Florence
  • Train from Florence to Rome
  • Hotel for 2 nights in Rome
  • Driving Time
    Pisa- San Gimignano: 1 hr. 25 mins. approx.
    San Gimignano - Siena: 50 mins. approx.
    Siena - Florence: 1 hr. 45 mins. approx.

Delight yourself in the charming Tuscany Region, during your vacations in Italy!. From Pisa (world-renowned Leaning Tower of Pisa), drive along the Tuscany visiting San Gimignano (medieval architecture, unique in the preservation of about a dozen of its tower houses) after that, Siena (medieval cityscape and the Palio, a horse race held in Piazza del Campo) and up to Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture). From there, catch a train to the fabulous Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food).

Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.

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