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The Best of Rome - Siena - Florence - Venice
15 to 22+ Nigths from $3,327*
This sample price: priced within the past 7 days for arrival on 9/23/2025, 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.
Most visited cities in Italy!. Explore Rome`s (the Eternal City) monuments, The Vatican and enjoy a evening food, after that, travel to Siena (a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) where to have a Cooking Class, and next, to Florence (capital of Italy’s Tuscany region), there have a Night Tour and visits to The Uffizi and Accademia, The Cathedral and a taste of its delicious food. Finally, visit Venice (set on gorgeous canals, intimate Gondola rides and under sculpted bridges), where to enjoy a Canal Cruise, a Doge`s Palace Visit and a delicious Food and Wine Tasting.

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
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This 15 night sample itinerary includes:
  • Flight into Rome and out of Venice
  • Hotel for 4 nights in Rome
  • Train from Rome to Siena
  • Hotel for 3 night in Siena
  • Train from Siena to Florence
  • Hotel for 4 nights in Florence
  • Train from Florence to Venice
  • Hotel for 4 nights in Venice

    Sample of Included Tours:
  • Guided City Tour in Rome
  • Colosseum, Palatine Hill and Roman Forum Tour in Rome
  • City Evening Food Tour around Rome
  • Vatican Museums and Sistine Chapel Tour from Rome
  • Guided City Tour in Siena
  • Italian Cooking Class in Siena
  • Night Time City Tour in Florence
  • Visit Uffizi and Accademia Museums in Florence
  • Food and Markets Tour around Florence
  • Visit to Florence Cathedral
  • Night Tour of Venice
  • Canal Cruise around Venice
  • Food and Wine Tastings around Venice
  • Visit to Doge`s Palace and St Mark`s Basilica in Venice

    Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.

Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 15 nights
3326.21 * incl.tax
Related Cities:
Rome (401)     Venice (218)     Florence (230)     Siena (29)    
Customize and Book
With Int'l Flight     Without Int'l Flight
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Cabin:
Destination
Arrival date
Stay
1. Rome
  646 hotels
2. Siena
   (43 hotels)
3. Florence
   (286 hotels)
4. 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
4 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!



3 nights in Siena

The beautiful town of Siena is the largest of the hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces.

Visit and discover the Cathedral of Santa Maria Assunta, Piazza del Campo, Palazzo Pubblico, Torre del Mangia, Biblioteca Piccolomini, Siena National Gallery, Church of San Domenico, Piazza Salimbeni, Porta Pispini, Siena Civic Museum and so much more.



4 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.



4 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   646 hotels offered
Optional   734 Things to do
Day 2
Overnight in Rome   646 hotels offered
Optional   734 Things to do
Day 3
Overnight in Rome   646 hotels offered
Optional   734 Things to do
Day 4
Overnight in Rome   646 hotels offered
Optional   734 Things to do
Day 5
Departing from Rome
Transportation to next city by: Train - Rome to Siena (Via Florence)
Siena
Day 5
Arrive to Siena
Overnight in Siena   43 hotels offered
Optional   97 Things to do
Day 6
Overnight in Siena   43 hotels offered
Optional   97 Things to do
Day 7
Overnight in Siena   43 hotels offered
Optional   97 Things to do
Day 8
Departing from Siena
Transportation to next city by: Train - Siena to Florence
Florence
Day 8
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 9
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 10
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 11
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 12
Departing from Florence
Transportation to next city by: Train - Florence to Venice
Venice
Day 12
Arrive to Venice
Overnight in Venice   233 hotels offered
Optional   613 Things to do
Day 13
Overnight in Venice   233 hotels offered
Optional   613 Things to do
Day 14
Overnight in Venice   233 hotels offered
Optional   613 Things to do
Day 15
Overnight in Venice   233 hotels offered
Optional   613 Things to do
Day 16
Departing from Venice

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Rome Hotels (646 total)
Siena Hotels (43 total)
Florence Hotels (286 total)
Venice Hotels (233 total)


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Tours in Rome (734 total)
Tours in Siena (97 total)
Tours in Florence (1338 total)
Tours in Venice (613 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):

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*Sample prices on display include ALL taxes & fuel surcharges... read more
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The Best of Rome - Siena - Florence - 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!
Siena
The beautiful town of Siena is the largest of the hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces.

Visit and discover the Cathedral of Santa Maria Assunta, Piazza del Campo, Palazzo Pubblico, Torre del Mangia, Biblioteca Piccolomini, Siena National Gallery, Church of San Domenico, Piazza Salimbeni, Porta Pispini, Siena Civic Museum 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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