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This sample price: priced within the past 7 days for arrival on 8/18/2025, 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.
One of our most popular vacation packages, offering an incredible introduction to Italy!. Discover Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food) after that, travel north to Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture), continue to Venice (set on gorgeous canals, intimate Gondola rides will guide you past sumptuous palaces and under sculpted bridges) and finish in Milan (one of the fashion and high-tech capitals of the world; known for the majestic Duomo Cathedral and the dazzling Vittorio Emanuele II shopping arcade). These destinations are connected by trains.
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 9 night sample itinerary includes:
Flight into Rome and out of Milan
Hotel for 3 nights in Rome
Train from Rome to Florence
Hotel for 2 nights in Florence
Train from Florence to Venice
Hotel for 2 nights in Venice
Train from Venice to Milan
Hotel for 2 nights in Milan
Price history for this itinerary (past 7 days):
From Atlanta ATL (GA), US for 9 nights
1711.86 * incl.tax
From Boston BOS (MA), US for 12 nights
1722.70 * incl.tax
From Charlotte CLT (NC), US for 9 nights
1571.38 * incl.tax
From Chicago CHI (All Airports)(IL), US for 11 nights
1388.75 * incl.tax
From Dallas DFW (TX), US for 9 nights
1485.39 * incl.tax
From Greenville GSP (SC), US for 9 nights
1704.13 * incl.tax
From Houston HOU (Hobby) (TX), US for 9 nights
1254.24 * incl.tax
From Kansas City MCI (MO), US for 11 nights
1626.42 * incl.tax
From Los Angeles LAX (CA), US for 9 nights
1086.03 * incl.tax
From Miami MIA (FL), US for 9 nights
1557.77 * incl.tax
From Montreal YUL (QC), CA for 9 nights
1775.03 * incl.tax
From New York City NYC (All Airports) (NY), US for 9 nights
1135.57 * incl.tax
From Norfolk ORF (VA), US for 9 nights
4927.21 * incl.tax
From Orlando MCO (FL), US for 9 nights
1263.65 * incl.tax
From Sacramento SMF (CA), US for 10 nights
1416.53 * incl.tax
From Salt Lake City SLC (UT), US for 9 nights
1537.52 * incl.tax
From San Diego SAN (CA), US for 9 nights
1301.05 * incl.tax
From San Francisco SFO (CA), US for 10 nights
1516.96 * incl.tax
From Savannah SAV (GA), US for 11 nights
1597.22 * incl.tax
From Seattle SEA (WA), US for 9 nights
1304.62 * incl.tax
From Spokane GEG (WA), US for 9 nights
1790.22 * incl.tax
From Washington WAS (All Airports)(DC), US for 9 nights
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!
2 nights in Milan
Milan is Italy's window on Europe, its most sophisticated and high-tech metropolis. La Scala, its landmark, is one of Europe's most prestigious opera houses. Milan is one of Europe's top shopping cities, with an incredible concentration of sophisticated, high style boutiques - and that's only fitting because Milan is the dynamo of the Italian fashion industry. Dolce & Gabbana, Ferré, Krizia, Moschino, Prada, Armani, and Versace have all catapulted to international stardom from design studios based here. Inevitably, shopping is of almost religious significance.
Discover The Last Supper by Michelangelo, The Duomo, Pinacoteca di Brera, Quadrilatero d'Oro, Galleria Vittorio Emanuele II, Scala museum and theatre, Piazza Fontana, Arco della Pace, the churches of Santa Maria delle Grazie and San Lorenzo, Corso Venezia and Piazza San Babila, Sforzesco Castle and so much more.
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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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Milan Hotels (211 total)
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Tours in Rome (734 total)
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Tours in Florence (1351 total)
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Tours in Venice (620 total)
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Tours in Milan (361 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.
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.
*Sample prices on display include ALL taxes & fuel surcharges... read more
close [x] * Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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Rome - Florence - Venice - Milan by Train
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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!
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.
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!
Milan is Italy's window on Europe, its most sophisticated and high-tech metropolis. La Scala, its landmark, is one of Europe's most prestigious opera houses. Milan is one of Europe's top shopping cities, with an incredible concentration of sophisticated, high style boutiques - and that's only fitting because Milan is the dynamo of the Italian fashion industry. Dolce & Gabbana, Ferré, Krizia, Moschino, Prada, Armani, and Versace have all catapulted to international stardom from design studios based here. Inevitably, shopping is of almost religious significance.
Discover The Last Supper by Michelangelo, The Duomo, Pinacoteca di Brera, Quadrilatero d'Oro, Galleria Vittorio Emanuele II, Scala museum and theatre, Piazza Fontana, Arco della Pace, the churches of Santa Maria delle Grazie and San Lorenzo, Corso Venezia and Piazza San Babila, Sforzesco Castle and so much more.