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Florence and Southern Tuscany with Signature Transfers

7 to 10+ Nights from $2,023*
* Sample price: priced within the past 7 days for a 12/6/2025 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
  • Transfer from Hotel in Florence to Hotel in Siena via Monteriggioni and San Gimignano
  • Hotel for 2 nights in Siena
  • Transfer from Hotel in Siena to Hotel in Cortona via Montepulciano
  • Hotel for 1 night in Cortona
  • Transfer from Hotel in Cortona to Hotel in Florence via Lucignano
  • Hotel for 1 night in Florence

Southern Tuscany Getaway!. From Florence (capital of Tuscany; home to Renaissance Art and Architecture), travel Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo). After that, have a pleasant stay at Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries). Finally, get back for one last night stay in Florence. Along your way, by door-to-door service between these destinations discover: medievals Monteriggioni and San Gimignano (famous towers and wine); Montepulciano and Lucignano.

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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  • Siena

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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.

  • 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.

  • 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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