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Florence and Cortona (Self Drive)

7 to 10+ Nights from $893*
* Sample price: priced within the past 7 days for a 11/5/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 7 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Rental Car for 5 days
  • Hotel for 3 nights in Cortona
  • Hotel for 1 night in Florence
  • Driving Time
    Florence - Cortona : 1 hr. 50 mins. approx.
    Cortona - Florence: 1 hr. 50 mins. approx.

Italian getaway by car!. Enjoy Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture) and after that, continue with your Rental Car to Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries). Drive back to Florence for one last stay, before returning home.

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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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Flexible Itinerary

  • Florence

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  • Cortona

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  • Florence

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Italy

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Trip Summary

  • Florence
    Florence

    The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

    Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

  • Cortona
    Cortona

    One of the oldest hill towns in Tuscany, surrounded by 3,000 year old Etruscan walls, Cortona retains much of its history through its architecture. The plain below is speckled with Etruscan tombs, but Cortona isn't just about the past; it is the setting for 'Under the Tuscan Sun' (book and movie), and has a thriving Expat community which is quite involved with the city.

    Visit and explore the Accademia Etrusca, Basilica of Saint Margaret of Cortona, Fortress of Girifalco, Diocesan Museum, Piazza della Repubblica, Convento di San Francesco and so much more.

  • Florence
    Florence

    The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

    Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

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