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Rome - Florence - Venice via Hilltowns and Ferrara with Private Transfers
7 to 10+ Nigths from $2,029*
This sample price: priced within the past 7 days for arrival on 8/5/2025, 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.
An enchanting journey through the best cities and breathtaking landscapes of Italy awaits! Discover Rome (the Eternal City) and after that, travel to Florence (the capital of Tuscany and cradle of the Renaissance), until you finally reach Venice (the intimate city of the canals). Enjoy private transfers en route that allow you to avoid the hassle of train stations and explore the following scenic Italian towns: Montepulciano (renowned for its exquisite Vino Nobile Wine), San Gimignano (characterized by its medieval architectural towers) and Ferrara (a well-preserved UNESCO-listed city with rich history).

The driver will give you time to explore these stops independently: Enjoy wandering the streets, shop, grab lunch, gelato, or coffee, and see the iconic landmarks before continuing your journey!

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
This 7 night sample itinerary includes:
  • Flight into Rome and out of Venice
  • Hotel for 3 nights in Rome
  • Transfer from Hotel in Rome to Hotel in Florence via Montepulciano and San Gimignano (with free time to explore on your own)
  • Hotel for 2 nights in Florence
  • Transfer from Hotel in Florence to Hotel in Venice via Ferrara (with free time to explore on your own)
  • Hotel for 2 nights in Venice
Price history for this itinerary (past 7 days):
From Boston BOS (MA), US for 7 nights
2273.62 * incl.tax
From Bristol/Johnson/Kingsport TRI (TN), US for 18 nights
3787.71 * incl.tax
From Chicago CHI (All Airports)(IL), US for 7 nights
2245.07 * incl.tax
From Fort Lauderdale FLL (FL), US for 7 nights
2307.54 * incl.tax
From Jacksonville JAX (FL), US for 7 nights
2521.37 * incl.tax
From Los Angeles LAX (CA), US for 7 nights
1951.51 * incl.tax
From Miami MIA (FL), US for 7 nights
2068.11 * incl.tax
From New York City NYC (All Airports) (NY), US for 7 nights
2023.28 * incl.tax
From Phoenix PHX (AZ), US for 10 nights
2625.38 * incl.tax
Related Itineraries:
Related Cities:
Rome (398)     Venice (217)     Florence (223)     San Gimignano (10)     Ferrara (5)     Montepulciano (1)    
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With Int'l Flight     Without Int'l Flight
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Cabin:
Destination
Arrival date
Stay
1. Rome
  654 hotels
2. Florence
   (284 hotels)
3. Venice
   (233 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 Rome

Rome is undeniably stunning, from its rich ancient culture, delectable cuisine and coffees to its uniquely European experiences. This city is packed full of sights; with thousands of years of history layered upon itself - you'll find everything from Roman ruins to Renaissance art. It's also home to Vatican City, and sights galore.

Explore and discover the Roman Colosseum and the Arch of Constantine, discover the Vatican, the smallest independent state in the world; throw a coin in the Trevi Fountain, marvel at the Pantheon, sit on the Spanish Steps, wander the Piazzas, eat the best gelato, climb Palatine Hill, walk the Ancient Appian Way and so much more!



2 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.



2 nights in Venice

With sumptuous palaces and romantic waterways, Venice is straight out of an 18th-century Canaletto masterpiece. No matter how many times you have seen it in movies or on TV, the real thing is more surreal and dreamlike than you ever imagined. Its landmarks, the Basilica di San Marco and the Palazzo Ducale are exotic melanges of Byzantine, Gothic, and Renaissance styles. It is full of secrets, ineffably romantic, and - at times - given over entirely to pleasure. You must walk everywhere in Venice; and where you cannot walk, you go by water.

Explore Piazza San Marco, stroll across the Rialto Bridge, get lost in the endless canals, admire the Basilica Santa Maria della Salute, visit the San Giorgio dei Greci, walk around the Jewish Ghetto, learn about Venice's musical history, tour Venice's unique architecture at Campo Santa Maria Formosa, celebrate one of Venice's many festivals, go window shopping, and so much more!



Book This Package
Flexible Itinerary
Rome
Day 1
Arrive to Rome
Overnight in Rome   654 hotels offered
Optional   736 Things to do
Day 2
Overnight in Rome   654 hotels offered
Optional   736 Things to do
Day 3
Overnight in Rome   654 hotels offered
Optional   736 Things to do
Day 4
Departing from Rome
Transportation to next city by: Regional Air
Florence
Day 4
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1352 Things to do
Day 5
Overnight in Florence   284 hotels offered
Optional   1352 Things to do
Day 6
Departing from Florence
Transportation to next city by: Regional Air
Venice
Day 6
Arrive to Venice
Overnight in Venice   233 hotels offered
Optional   620 Things to do
Day 7
Overnight in Venice   233 hotels offered
Optional   620 Things to do
Day 8
Departing from Venice
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Rome Hotels (654 total)
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Florence Hotels (284 total)
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Venice Hotels (233 total)
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Tours in Rome (736 total)
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Tours in Florence (1352 total)
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Tours in Venice (620 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.
Italy
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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):

Your Preferred Major Airport:

*Sample prices on display include ALL taxes & fuel surcharges... read more
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Rome - Florence - Venice via Hilltowns and Ferrara with Private Transfers
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Map
Rome
Rome is undeniably stunning, from its rich ancient culture, delectable cuisine and coffees to its uniquely European experiences. This city is packed full of sights; with thousands of years of history layered upon itself - you'll find everything from Roman ruins to Renaissance art. It's also home to Vatican City, and sights galore.

Explore and discover the Roman Colosseum and the Arch of Constantine, discover the Vatican, the smallest independent state in the world; throw a coin in the Trevi Fountain, marvel at the Pantheon, sit on the Spanish Steps, wander the Piazzas, eat the best gelato, climb Palatine Hill, walk the Ancient Appian Way and so much more!
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.
Venice
With sumptuous palaces and romantic waterways, Venice is straight out of an 18th-century Canaletto masterpiece. No matter how many times you have seen it in movies or on TV, the real thing is more surreal and dreamlike than you ever imagined. Its landmarks, the Basilica di San Marco and the Palazzo Ducale are exotic melanges of Byzantine, Gothic, and Renaissance styles. It is full of secrets, ineffably romantic, and - at times - given over entirely to pleasure. You must walk everywhere in Venice; and where you cannot walk, you go by water.

Explore Piazza San Marco, stroll across the Rialto Bridge, get lost in the endless canals, admire the Basilica Santa Maria della Salute, visit the San Giorgio dei Greci, walk around the Jewish Ghetto, learn about Venice's musical history, tour Venice's unique architecture at Campo Santa Maria Formosa, celebrate one of Venice's many festivals, go window shopping, and so much more!

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