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Florence - Southern Tuscany and Positano (Self Drive)
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10 to 15+ Nigths from $2,402*
This sample price: priced within the past 7 days for arrival on 9/15/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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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 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.
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.

Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 10 nights
2401.70 * incl.tax
From Pensacola PNS (FL), US for 10 nights
4278.17 * incl.tax
Related Itineraries:
Related Cities:
Positano (7)     Naples (41)     Florence (223)     Southern Tuscany (13)     Amalfi Coast (24)    
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With Int'l Flight     Without Int'l Flight
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Cabin:
Destination
Arrival date
Stay
1. Florence
  284 hotels
2. Southern Tuscany
   (144 hotels)
3. Positano
   (39 hotels)
4. Naples
   (68 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
3 nights in 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.



3 nights in Southern Tuscany

The hill towns and valleys south of Siena comprise 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 road passes, isolated farmhouses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a rural setting, and thermal spas dating from long times past. 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.

Southern Tuscany's cities are textbook Italian hill towns. This is Etruscan country, where the necropolis near Sovana hints at a rich and somewhat mysterious pre-Roman civilization, where Roman settlements like Montalcino and Montepulciano grew into medieval cities and today produce two of Italy's top red wines, the powerhouse Brunello di Montalcino and the noble Vino Nobile di Montepulciano.



3 nights in Positano

Positano seems to be standing, leaning against the jagged mountain rock face, with many multicolored houses that seem to be built in a single cluster, all on top of each other. The town is very unique and incredibly attractive. It is the kingdom of many flights of little steps, of narrow passageways enlivened and colored by wonderful shops, lively bars and cafes, and restaurants that specialize in seafood.

Visit and explore the Ruins from Roman settlements which are found near the Church of Assunta. The majolica tiled dome of the Collegiate Church of Santa Maria Assunta can be seen from every corner of the town and the beaches of Positano are formed from volcanic sand and small stones, which lend to the background and so much more.



1 nights in Naples

The proximity of the city of Naples (Napoli) to the Vesuvius gives its inhabitants a certain edge. Its reputation as the most vibrant city in Italy can be a double-edged sword, explaining why some tourists like it and some hate it outright. Nonetheless, the charm of Naples resides in its narrow streets with numerous ancient churches, street markets, cafes, bars and restaurants, all leading to a 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.



Book This Package
Flexible Itinerary
Florence
Day 1
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 2
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 3
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 4
Departing from Florence
Transportation to next city by: Regional Air
Southern Tuscany
Day 4
Arrive to Southern Tuscany
Overnight in Southern Tuscany   144 hotels offered
Day 5
Overnight in Southern Tuscany   144 hotels offered
Day 6
Overnight in Southern Tuscany   144 hotels offered
Day 7
Departing from Southern Tuscany
Transportation to next city by: Regional Air
Positano
Day 7
Arrive to Positano
Overnight in Positano   39 hotels offered
Optional   109 Things to do
Day 8
Overnight in Positano   39 hotels offered
Optional   109 Things to do
Day 9
Overnight in Positano   39 hotels offered
Optional   109 Things to do
Day 10
Departing from Positano
Transportation to next city by: Regional Air
Naples
Day 10
Arrive to Naples
Overnight in Naples   68 hotels offered
Optional   412 Things to do
Day 11
Departing from Naples
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Florence Hotels (284 total)
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Southern Tuscany Hotels (144 total)
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Positano Hotels (39 total)
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Naples Hotels (68 total)
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Tours in Florence (1350 total)
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Tours in Positano (109 total)
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Tours in Naples (412 total)
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Package Map Picture
Italy

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.
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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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Florence - Southern Tuscany and Positano (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.
Southern Tuscany
The hill towns and valleys south of Siena comprise 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 road passes, isolated farmhouses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a rural setting, and thermal spas dating from long times past. 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.

Southern Tuscany's cities are textbook Italian hill towns. This is Etruscan country, where the necropolis near Sovana hints at a rich and somewhat mysterious pre-Roman civilization, where Roman settlements like Montalcino and Montepulciano grew into medieval cities and today produce two of Italy's top red wines, the powerhouse Brunello di Montalcino and the noble Vino Nobile di Montepulciano.
Positano
Positano seems to be standing, leaning against the jagged mountain rock face, with many multicolored houses that seem to be built in a single cluster, all on top of each other. The town is very unique and incredibly attractive. It is the kingdom of many flights of little steps, of narrow passageways enlivened and colored by wonderful shops, lively bars and cafes, and restaurants that specialize in seafood.

Visit and explore the Ruins from Roman settlements which are found near the Church of Assunta. The majolica tiled dome of the Collegiate Church of Santa Maria Assunta can be seen from every corner of the town and the beaches of Positano are formed from volcanic sand and small stones, which lend to the background and so much more.
Naples
The proximity of the city of Naples (Napoli) to the Vesuvius gives its inhabitants a certain edge. Its reputation as the most vibrant city in Italy can be a double-edged sword, explaining why some tourists like it and some hate it outright. Nonetheless, the charm of Naples resides in its narrow streets with numerous ancient churches, street markets, cafes, bars and restaurants, all leading to a 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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