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Florence - San Gimignano - Rome (Self Drive)

4.2 out of 5 stars
5 Customer Feedbacks 5 Customer Feedbacks
9 to 13+ Nights from $2,635*
* Sample price: priced within the past 7 days for a 10/20/2025 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 Florence and out of Rome
  • Hotel for 3 nights in Florence
  • Rental Car for 4 days
  • Hotel for 3 nights in San Gimignano
  • Hotel for 3 nights in Rome
  • Driving Time
    Florence - San Gimignano: 1 hr. 10 mins. approx.
    San Gimignano - Rome: 3 hrs. 20 mins. approx.

A Self Drive Vacation to some of our most popular destinations in Italy!. Spend a few days in artistic Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), then pick up your Rental Car and drive for a visit to San Gimignano (famous for its medieval architecture and towers). Finish with a stay in monumental Rome (the Eternal City, with its stunning Colosseum, Roman Forum 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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Flexible Itinerary

  • Florence

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  • San Gimignano

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  • Rome

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Italy

Customer Reviews

4.2 out of 5 stars

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.

  • San Gimignano
    San Gimignano

    San Gimignano is a small medieval hill town enclosed with 13th-century walls and accessed by two main streets that intersect to create two wonderful piazzas. Known as the 'City of Beautiful Towers', it is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls create a remarkable skyline. Truly a little gem, it has been declared a World Heritage Site by UNESCO.

    Visit and explore the amazing Terme di Petriolo, Volterra, Colle Val d'Elsa, Montaione, Pienza, Bagno Vignoni and so much more.

  • Rome
    Rome

    Rome is undeniably stunning, from its rich ancient culture, delectable cuisine and coffees to its uniquely European experiences. This city is packed full of sights; with thousands of years of history layered upon itself - you'll find everything from Roman ruins to Renaissance art. It's also home to Vatican City, and sights galore.

    Explore and discover the Roman Colosseum and the Arch of Constantine, discover the Vatican, the smallest independent state in the world; throw a coin in the Trevi Fountain, marvel at the Pantheon, sit on the Spanish Steps, wander the Piazzas, eat the best gelato, climb Palatine Hill, walk the Ancient Appian Way and so much more!

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