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Rome - Florence - Chianti and Venice
4 Customer Feedbacks
11 to 16+ Nigths from $1,801*
This sample price: priced within the past 7 days for arrival on 7/15/2025, 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.
Charming Italy Countryside!. Spend a few days visiting Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food) after that, take a train to Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) for a visit. From there, pick up the Rental Car, for an enchanting visit to the Chianti Wine Region (beautiful and famous region of Tuscany with best wineries). Drive back Florence to drop the car, and after that, continue by train to ultra-romantic Venice (set on gorgeous canals, intimate Gondola rides will guide you past sumptuous palaces and under sculpted bridges). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 11 night sample itinerary includes:
  • Flight into Rome and out of Venice
  • Hotel for 3 nights in Rome
  • Train from Rome to Florence
  • Hotel for 2 nights in Florence
  • Rental Car for 4 days
  • Hotel for 3 nights in Chianti Wine Region
  • Hotel for 1 night in Florence
  • Train from Florence to Venice
  • Hotel for 2 nights in Venice

  • Driving Time
    Florence - Chianti Wine Region 1 hr. / 1hr. 30 mins. approx.
    Chianti Wine Region - Florence: 1 hr. / 1hr. 30 mins. approx.

Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 11 nights
1800.64 * incl.tax
Related Itineraries:
Related Cities:
Rome (398)     Venice (217)     Florence (223)     Chianti Wine Region (11)    
Customize and Book
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. Chianti Wine Region
   (51 hotels)
4. Florence
   (284 hotels)
5. 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.



3 nights in Chianti Wine Region

Chianti, located in the center of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.

Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni and so much more.



1 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   734 Things to do
Day 2
Overnight in Rome   654 hotels offered
Optional   734 Things to do
Day 3
Overnight in Rome   654 hotels offered
Optional   734 Things to do
Day 4
Departing from Rome
Transportation to next city by: Train - Rome to Florence
Florence
Day 4
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 5
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 6
Departing from Florence
Transportation to next city by: Regional Air
Chianti Wine Region
Day 6
Arrive to Chianti Wine Region
Overnight in Chianti Wine Region   51 hotels offered
Optional   37 Things to do
Day 7
Overnight in Chianti Wine Region   51 hotels offered
Optional   37 Things to do
Day 8
Overnight in Chianti Wine Region   51 hotels offered
Optional   37 Things to do
Day 9
Departing from Chianti Wine Region
Transportation to next city by: Regional Air
Florence
Day 9
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1350 Things to do
Day 10
Departing from Florence
Transportation to next city by: Train - Florence to Venice
Venice
Day 10
Arrive to Venice
Overnight in Venice   233 hotels offered
Optional   620 Things to do
Day 11
Overnight in Venice   233 hotels offered
Optional   620 Things to do
Day 12
Departing from Venice
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Rome Hotels (654 total)
›
Florence Hotels (284 total)
›
Chianti Wine Region Hotels (51 total)
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Venice Hotels (233 total)
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Tours in Rome (734 total)
›
Tours in Florence (1350 total)
›
Tours in Chianti Wine Region (37 total)
›
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.
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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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Rome - Florence - Chianti and Venice
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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.
Chianti Wine Region
Chianti, located in the center of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.

Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni 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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