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Rome - Siena - Pisa - Florence - Assisi - Rome by Train
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9 to 13+ Nigthsfrom $1,441*
This sample price: priced within the past 7 days for arrival on 9/9/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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.
Magical Italy by train!. Start in Rome (the Eternal City) then, travel to Siena (quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and after that, visit Pisa (world-renowned Leaning Tower of Pisa and many other architectural wonders). Continue to Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), and next is Assisi (birthplace of St. Francis, Italy's patron saint, Assisi lies amid Umbria's rolling hills). Finish this trip, returning to Rome for one last night stay.
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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 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.
1 nights in Pisa
Pisa is a legendary city and one of the most famous in this region of Italy. Although best known for the world famous Leaning Tower, there are many other architectural and artistic marvels worth seeing in this beautiful city. Pisa is located on the western coast only 20 minutes from the Ligurian Sea and has great transport links to Florence, Livorno and La Spezia. It is one of the smaller cities in Tuscany, but has historically been one of the most important and influential.
Visit and explore the Cathedral of Santa Maria Assunta, Leaning Tower of Pisa, The Baptistery, Campo Santo, Museo Nazionale, Santa Maria della Spina, Palazzo dei Cavalieri, Museo dell’Opera del Duomo, Borgo Stretto, Guelph Tower 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.
1 nights in Assisi
Assisi is a medieval hill town, known for being the birthplace of Saint Francis, and a UNESCO World Heritage Site. The town represents 'a series of masterpieces of man's creative spirit,' and everything revolves around its most renowned citizen, St. Francis, Patron Saint of Italy, from the Basilica, which is dedicated to the Saint and contains his tomb, to the hermitage (Eremo delle Carceri), located a few miles outside the town walls, where St. Francis used to retreat in prayer.
Visit and explore the Basilica of Saint Francis (UNESCO World Heritage Site from the 13th century), the Church of Santa Chiara (houses the San Damiano Crucifix which spoke to Francis in 1206), San Rufino Cathedral (12th century Romanesque facade), Rocca Maggiore Castle, a Roman Amphitheater from the first century surrounded by medieval houses, and so much more.
1 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!
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.
Rome - Siena - Pisa - Florence - Assisi - Rome 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 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.
Pisa is a legendary city and one of the most famous in this region of Italy. Although best known for the world famous Leaning Tower, there are many other architectural and artistic marvels worth seeing in this beautiful city. Pisa is located on the western coast only 20 minutes from the Ligurian Sea and has great transport links to Florence, Livorno and La Spezia. It is one of the smaller cities in Tuscany, but has historically been one of the most important and influential.
Visit and explore the Cathedral of Santa Maria Assunta, Leaning Tower of Pisa, The Baptistery, Campo Santo, Museo Nazionale, Santa Maria della Spina, Palazzo dei Cavalieri, Museo dell’Opera del Duomo, Borgo Stretto, Guelph Tower 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.
Assisi is a medieval hill town, known for being the birthplace of Saint Francis, and a UNESCO World Heritage Site. The town represents 'a series of masterpieces of man's creative spirit,' and everything revolves around its most renowned citizen, St. Francis, Patron Saint of Italy, from the Basilica, which is dedicated to the Saint and contains his tomb, to the hermitage (Eremo delle Carceri), located a few miles outside the town walls, where St. Francis used to retreat in prayer.
Visit and explore the Basilica of Saint Francis (UNESCO World Heritage Site from the 13th century), the Church of Santa Chiara (houses the San Damiano Crucifix which spoke to Francis in 1206), San Rufino Cathedral (12th century Romanesque facade), Rocca Maggiore Castle, a Roman Amphitheater from the first century surrounded by medieval houses, 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!
