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

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10 to 15+ Nights from $1,536*
* Sample price: priced within the past 7 days for a 4/20/2026 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 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).

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Flexible Itinerary

  • Pisa

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  • San Gimignano

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  • Siena

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  • Florence

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  • Rome

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Italy

Customer Reviews

4.6 out of 5 stars

Trip Summary

  • Pisa
    Pisa

    Pisa is a legendary city and one of the most famous in this region of Italy. Although best known for the world famous Leaning Tower, there are many other architectural and artistic marvels worth seeing in this beautiful city. Pisa is located on the western coast only 20 minutes from the Ligurian Sea and has great transport links to Florence, Livorno and La Spezia. It is one of the smaller cities in Tuscany, but has historically been one of the most important and influential.

    Visit and explore the Cathedral of Santa Maria Assunta, Leaning Tower of Pisa, The Baptistery, Campo Santo, Museo Nazionale, Santa Maria della Spina, Palazzo dei Cavalieri, Museo dell’Opera del Duomo, Borgo Stretto, Guelph Tower 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.

  • Siena
    Siena

    The beautiful town of Siena is the largest of the hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces.

    Visit and discover the Cathedral of Santa Maria Assunta, Piazza del Campo, Palazzo Pubblico, Torre del Mangia, Biblioteca Piccolomini, Siena National Gallery, Church of San Domenico, Piazza Salimbeni, Porta Pispini, Siena Civic Museum 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.

  • 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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