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Florence - Southern Tuscany and Sorrento (Self Drive)
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10 to 15+ Nigthsfrom $1,670*
This sample price: priced within the past 7 days for arrival on 9/1/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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3 Customer FeedbacksHotels were modest but comfortable and staff were friendly and helpful. We experienced no ...
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Visit two of Italy`s most charming regions with a Rental Car!. Start in Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (boasting the most captivating countryside and vineyards that produce Tuscany's mightiest red wines in cities like: Montepulciano, San Gimignano, Pienza and Volterra) and after that, to Sorrento (with more than two-thirds the year spent drenched in sunshine) in the Neapolitan Riviera. Finish this trip, driving to Naples to drop off the car and to catch your flight back home.
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
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.
3 nights in 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.
3 nights in Sorrento
Sorrento is the best known town on the Neapolitan Riviera. It's situated in a stunning location on a long cliff overlooking the sea, and surrounded by lemon and olive groves. Sorrento offers charming cobblestone streets, alluring lungomare (seafront promenades), colorful and fragrant flowers, and a lively cultural scene. The old town still retains its Roman grid of narrow streets and its centro storico (historic center) is alive with cafes, clubs, and restaurants, which become an exciting atmosphere during the sweet nights of summer.
Visit and discover Marina Grande and Marina Piccola, Cloister of San Francesco, Bagni della Regina Giovanna, Cathedral and Bell Tower, Basilica of Sant'Antonino, Villa Comunale, Correale di Terranova Museum, Museo-Bottega della Tarsia Lignea (Wooden Marquetry Shop-Museum), and so much more.
1 nights in 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.
For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
Florence - Southern Tuscany and Sorrento (Self Drive)
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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.
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.
Sorrento is the best known town on the Neapolitan Riviera. It's situated in a stunning location on a long cliff overlooking the sea, and surrounded by lemon and olive groves. Sorrento offers charming cobblestone streets, alluring lungomare (seafront promenades), colorful and fragrant flowers, and a lively cultural scene. The old town still retains its Roman grid of narrow streets and its centro storico (historic center) is alive with cafes, clubs, and restaurants, which become an exciting atmosphere during the sweet nights of summer.
Visit and discover Marina Grande and Marina Piccola, Cloister of San Francesco, Bagni della Regina Giovanna, Cathedral and Bell Tower, Basilica of Sant'Antonino, Villa Comunale, Correale di Terranova Museum, Museo-Bottega della Tarsia Lignea (Wooden Marquetry Shop-Museum), and so much more.
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.
