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Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)

9 to 13+ Nights from $1,703*
* Sample price: priced within the past 7 days for a 11/24/2025 arrival, departing Tampa TPA (FL), US. Choose departure city, cabin and dates.

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This 9 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 2 nights in Florence
  • Rental Car for 6 days
  • Hotel for 2 nights in Lucca
  • Hotel for 2 nights in San Gimignano
  • Hotel for 2 nights in Siena
  • Hotel for 1 night in Florence

Focus your visit to Italy in wonderful Tuscany!. Visit artistic Florence, then pick up your car and spend some leisurely days staying in Lucca, San Gimignano and Siena to be able to experience all the different aspects of this charming region. Return to Florence for one last stay.

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
Live phone and chat support

Flexible Itinerary

  • Florence

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  • Lucca

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  • San Gimignano

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  • Siena

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  • Florence

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Italy

Customer Reviews

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.

  • 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.

  • 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.

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