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This sample price: priced within the past 7 days for arrival on 9/29/2025, 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.
Visit Florence and Umbria!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills) with a stop in Loro Ciuffenna and Perugia. After that, visit Orvieto (a small city perched on a rock cliff in Umbria, Italy) with a stop in Montepulciano and Lucignano. Lastly, Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo) with a stop in Montepulciano and Lucignano. Before heading back home, return to Florence with a stop in Monteriggioni and San Gimignano.
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 8 night sample itinerary includes:
Flight into and out of Florence
Hotel for 3 nights in Florence
Transfer from Hotel in Florence to Hotel in Assisi via Loro Ciuffenna and Perugia
Hotel for 2 nights in Assisi
Transfer from Hotel in Assisi to Hotel in Orvieto Via Todi
Hotel for 1 night in Orvieto
Transfer from Hotel in Orvieto to Hotel in Siena via Montepulciano and Lucignano
Hotel for 1 night in Siena
Transfer from Hotel in Siena to Hotel in Florence via Monteriggioni and San Gimignano
Hotel for 1 night in Florence
Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 8 nights
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 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 Orvieto
Orvieto is one of the most dramatic hill towns in Italy, rising above the almost vertical faces of tufa cliffs that are completed by defensive walls built of the same stone. The main attraction of the town is the spectacular Duomo, one of Italy's finest Gothic buildings, dating from 1290. Its glittering mosaic facade is visible for miles around. The Gothic style interior holds frescoes by Fra Angelico and Signorelli and beautiful wooden choir stalls.
Visit and discover the Duomo, Saint Patrick's Well, the underground city and passages, the Torre del Moro, the Albornz Fortress, other Etruscan sites like the remnants of the Etruscan wall around the town, tombs and a necropolis, and so much more!
1 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 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.
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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Florence and Umbria with Signature Transfers
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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.
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.
Orvieto is one of the most dramatic hill towns in Italy, rising above the almost vertical faces of tufa cliffs that are completed by defensive walls built of the same stone. The main attraction of the town is the spectacular Duomo, one of Italy's finest Gothic buildings, dating from 1290. Its glittering mosaic facade is visible for miles around. The Gothic style interior holds frescoes by Fra Angelico and Signorelli and beautiful wooden choir stalls.
Visit and discover the Duomo, Saint Patrick's Well, the underground city and passages, the Torre del Moro, the Albornz Fortress, other Etruscan sites like the remnants of the Etruscan wall around the town, tombs and a necropolis, 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.
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.
From New York City NYC (All Airports) (NY), US for 8 nights
