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This sample price: priced within the past 7 days for arrival on 12/16/2025, departure from Chicago CHI (All Airports)(IL), 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.
Start in romantic Venice, then catch a train to artistic Florence, then catch the train to Imperial Rome. After your visit to Rome, pick up your car for a drive to the incredible ruins of Pompeii and end with a beautiful stay in Sorrento on the Neapolitan Riviera.
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 11 night sample itinerary includes:
Flight into Venice and out of Naples
Hotel for 2 nights in Venice
Train - Venice to Florence
Hotel for 2 nights in Florence
Train - Florence to Rome
Hotel for 3 nights in Rome
Rent a car for 5 days
Hotel for 1 night in Pompeii
Hotel for 2 nights in Sorrento
Hotel for 1 night in Naples
Price history for this itinerary (past 7 days):
From Boston BOS (MA), US for 17 nights
2834.86 * incl.tax
From Chicago CHI (All Airports)(IL), US for 11 nights
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 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 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!
1 nights in Pompeii
Pompeii, the city buried in 79 AD is the queen of archaeological sites, and big enough to hold the millions of visitors it attracts. Destroyed in AD 79 by the terrible eruption of Vesuvius (at the same time as Herculaneum and Stabiae), Pompeii remained buried under a thick layer of ash until the 18C. As a result of this disaster, this small prosperous Roman town has been preserved in an almost perfect state, providing important archaeological information on everyday life during the Roman Empire. A walk around thus vast complex of ruins is a fascinating and moving experience.
Visit and explore the Forum, The Brothel, Teatro Grande, the amphitheater, Great Palestra, Thermae Stabiane, House of Menander, House of the Marine Venus, House of the Vettii , The House of the Tragic Poet , The Temple of Isis and Villa dei Misteri and so much more.
2 nights in Sorrento
The best-known town on the Neapolitan Riviera is Sorrento, which is situated in a stunning location, on a long cliff amid lemon and olive groves overlooking the sea. Sorrento offers charming cobblestone streets, alluring lungomare (seafront promenade), colorful and fragrant flowers, and a lively cultural scene. The old town still retains its Roman grid of narrow streets and its centro storico are alive with cafes, clubs, and restaurants, which become an exciting atmosphere during the sweet nights of summer.
Visit and discover Marina Grande and Marina Piccola, Cloister of San Francesco, Bagni della Regina Giovanna, Cathedral and Bell Tower, Basilica of Sant'Antonino, Villa Comunale, Correale di Terranova Museum, Museo-Bottega della Tarsia Lignea (Wooden Marquetry Shop-Museum), 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.
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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Venice - Florence - Rome - Sorrento with Pompeii
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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!
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.
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!
Pompeii, the city buried in 79 AD is the queen of archaeological sites, and big enough to hold the millions of visitors it attracts. Destroyed in AD 79 by the terrible eruption of Vesuvius (at the same time as Herculaneum and Stabiae), Pompeii remained buried under a thick layer of ash until the 18C. As a result of this disaster, this small prosperous Roman town has been preserved in an almost perfect state, providing important archaeological information on everyday life during the Roman Empire. A walk around thus vast complex of ruins is a fascinating and moving experience.
Visit and explore the Forum, The Brothel, Teatro Grande, the amphitheater, Great Palestra, Thermae Stabiane, House of Menander, House of the Marine Venus, House of the Vettii , The House of the Tragic Poet , The Temple of Isis and Villa dei Misteri and so much more.
The best-known town on the Neapolitan Riviera is Sorrento, which is situated in a stunning location, on a long cliff amid lemon and olive groves overlooking the sea. Sorrento offers charming cobblestone streets, alluring lungomare (seafront promenade), colorful and fragrant flowers, and a lively cultural scene. The old town still retains its Roman grid of narrow streets and its centro storico are alive with cafes, clubs, and restaurants, which become an exciting atmosphere during the sweet nights of summer.
Visit and discover Marina Grande and Marina Piccola, Cloister of San Francesco, Bagni della Regina Giovanna, Cathedral and Bell Tower, Basilica of Sant'Antonino, Villa Comunale, Correale di Terranova Museum, Museo-Bottega della Tarsia Lignea (Wooden Marquetry Shop-Museum), and so much more.
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.
From Boston BOS (MA), US for 17 nights
