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Florence - Southern Tuscany and Positano (Self Drive)

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10 to 15+ Nights from $2,150*
* Sample price: priced within the past 7 days for a 8/8/2025 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 Florence and out of Naples
  • Hotel for 3 nights in Florence
  • Rental Car for 8 days
  • Hotel for 3 nights in Southern Tuscany
  • Hotel for 3 nights in Positano
  • Hotel for 1 night in Naples
  • Driving Time
    Florence - Southern Tuscany Area: 1 hr. 10 - 50 mins. approx.
    Southern Tuscany - Positano: 5 hrs. 10 - 55 mins. approx.
    Positano - Naples: 1 hr. 20 mins. approx.

Visit two of Italy`s most charming regions, with this holiday package!. From Florence (capital of Italy’s Tuscany region, home to many masterpieces of Renaissance art and architecture); pick up the Rental Car and drive along the beautiful Southern Tuscany (renowned as one of the world's best wine regions, like Chianti, with its hilltop towns and lush landscapes, delicious dishes and art). From there, drive down the south to Amalfi Coast (with its breathtaking views, famous for its cuisine and its production of limoncello liqueur), until your next destination; Positano (a picturesque beach town with splendid coastline; famous for its colorful buildings, excellent restaurants, and mild climate). Finish this trip, driving to Naples (home place of Pizza; also known for its natural beauties, such as Posillipo, Phlegraean Fields, Nisida, and Vesuvius) for one last stay before returning home!. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Florence

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  • Southern Tuscany

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  • Positano

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  • Naples

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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.

  • Southern Tuscany
    Southern Tuscany

    The hill towns and valleys south of Siena comprise what is perhaps Tuscany's most captivating and picturesque region. Much of the area is filled with the expansive and beautiful Val d'Orcia (most people's idealized picture of Tuscany). It is a land of medieval castles guarding narrow passes, isolated farm houses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a rural setting, and thermal spas dating from times long ago. Most of the region has been landscaped over thousands of years, turning the low, rolling hills into farmlands and vineyards that produce Tuscany's mightiest red wines.

    Visit and discover Montepulciano, Pienza, Chianciano Terme, Terme di Petriolo, and Bagno Vignoni, the necropolis near Sovana, thermal spas, and vineyards that produce two of Italy's top red wines.

  • Positano
    Positano

    Positano really is a dream! Colorful houses painted shades of pink, white, and yellow appear to cling tightly to the jagged mountain rock face, but are actually very accessible through the narrow streets that snake their way up the steep mountainside. The unique cliffside setting is what gives most of the town its amazing views. Even to many Italians, Positano represents the perfect Italian holiday with its fashionable people, gorgeous location, amazing food and wine, and vibrant nightlife. Positano is called the 'pearl of the Amalfi Coast,' not only for the many terraces, stairways, and colorful houses, but also for the emotions it evokes in all who visit.

    Visit and explore Roman ruins near the Church of Assunta, see the majolica tiled dome of the Collegiate Church of Santa Maria Assunta, lounge on the beaches of Positano, which are formed from volcanic sand and small stones, and so much more.

  • Naples
    Naples

    Naples reputation as the most vibrant city in Italy can be a double-edged sword, explaining why some tourists love it and others hate it outright. As far as Italian cliches go, Naples seems to encapsulate them all, from the home of pizza and gelato to mandolin playing musicians. Nonetheless, the charm of Naples resides in its narrow streets, ancient churches, street markets, cafes, bars and restaurants, all contributing to the cacophony of sounds and images embodying the spirit of the Italian South.

    Visit and discover the Ancient Ruins of Pompeii, Climb Mount Vesuvius, sail to the Island of Capri, explore the Nativity Markets, visit the National Archaeological Museum, the Secret Underground World and the San Gennaro Catacombs, visit the Ruins of Herculaneum, enjoy the Piazzas of the city, and so much more.

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