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Florence - Umbria - Tuscany: Chauffeured Collection

8 to 12+ Nights from $2,211*
* Sample price: priced within the past 7 days for a 1/27/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 8 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Transfer from Hotel in Florence to Hotel in Assisi via Loro Ciuffenna and Perugia
  • Hotel for 2 nights in Assisi
  • Transfer from Hotel in Assisi to Hotel in Cortona via Castiglio Fiorentino
  • Hotel for 1 night in Cortona
  • Transfer from Hotel in Cortona to Hotel in Lucca via Pisa and Montecatini Alto
  • Hotel for 1 night in Lucca
  • Transfer from Hotel in Lucca to Hotel in Florence via Prato
  • Hotel for 1 night in Florence

Explore Italy!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills) with a stop in Loro Ciuffenna and Perugia. After that, visit Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries) with a stop in Castiglio Fiorentino. Lastly, Lucca (it is known throughout Italy for its fantastic medieval city walls that still encircle most of the historic old town) with a stop in Pisa and Montecatini Alto. Before heading back home, return to Florence with a stop in Prato.

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  • Assisi

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  • Cortona

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  • Lucca

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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.

  • Assisi
    Assisi

    Assisi is a medieval hill town, known for being the birthplace of Saint Francis, and a UNESCO World Heritage Site. The town represents 'a series of masterpieces of man's creative spirit,' and everything revolves around its most renowned citizen, St. Francis, Patron Saint of Italy, from the Basilica, which is dedicated to the Saint and contains his tomb, to the hermitage (Eremo delle Carceri), located a few miles outside the town walls, where St. Francis used to retreat in prayer.

    Visit and explore the Basilica of Saint Francis (UNESCO World Heritage Site from the 13th century), the Church of Santa Chiara (houses the San Damiano Crucifix which spoke to Francis in 1206), San Rufino Cathedral (12th century Romanesque facade), Rocca Maggiore Castle, a Roman Amphitheater from the first century surrounded by medieval houses, 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.

  • Lucca
    Lucca

    Lovely Lucca is one of Tuscany's true gems. This little medieval city is located very close to Pisa, but much more attractive and charming. You enter the historic town via one of the four gates in the city's walls. As Lucca has not seen a war since the 1400s, the architecture with the historic center (inside the walls) is well-preserved and features beautiful churches and remains of a Roman amphitheater. If you plan to travel to Tuscany, you should not miss this city.

    Discover and visit the Roman Amphitheater, Duomo di San Martino, Torre Guinigi, Torre delle Ore, Palazzo Mansi, Saint Michael's Church, San Frediano's Church, Via Fillungo (main street), Palazzo Pfanner, Piazza Napoleone, Domus Romana, 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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