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Florence - Umbria - Tuscany with Signature Transfers
8 to 12+ Nigths from $2,943*
This sample price: priced within the past 7 days for arrival on 1/16/2026, departure from Dallas DFW (TX), 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.
Explore Italy!. 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 Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries) with a stop in Castiglio Fiorentino. Lastly, Lucca (it is known throughout Italy for its fantastic medieval city walls that still encircle most of the historic old town) with a stop in Pisa and Montecatini Alto. Before heading back home, return to Florence with a stop in Prato.

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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 Cortona via Castiglio Fiorentino
  • Hotel for 1 night in Cortona
  • Transfer from Hotel in Cortona to Hotel in Lucca via Pisa and Montecatini Alto
  • Hotel for 1 night in Lucca
  • Transfer from Hotel in Lucca to Hotel in Florence via Prato
  • Hotel for 1 night in Florence
Price history for this itinerary (past 7 days):
From Dallas DFW (TX), US for 8 nights
2942.42 * incl.tax
From New York City NYC (All Airports) (NY), US for 8 nights
3034.87 * incl.tax
Related Itineraries:
Related Cities:
Pisa (20)     Assisi (14)     Florence (230)     Perugia (6)     Lucca (14)     Cortona (3)     Prato (2)    
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With Int'l Flight     Without Int'l Flight
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Cabin:
Destination
Arrival date
Stay
1. Florence
  286 hotels
2. Assisi
   (44 hotels)
3. Cortona
   (10 hotels)
4. Lucca
   (41 hotels)
5. Florence
   (286 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
3 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 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 Cortona

One of the oldest hill towns in Tuscany, surrounded by 3,000 year old Etruscan walls, Cortona retains much of its history through its architecture. The plain below is speckled with Etruscan tombs, but Cortona isn't just about the past; it is the setting for 'Under the Tuscan Sun' (book and movie), and has a thriving Expat community which is quite involved with the city.

Visit and explore the Accademia Etrusca, Basilica of Saint Margaret of Cortona, Fortress of Girifalco, Diocesan Museum, Piazza della Repubblica, Convento di San Francesco and so much more.



1 nights in Lucca

Lovely Lucca is one of Tuscany's true gems. This little medieval city is located very close to Pisa, but much more attractive and charming. You enter the historic town via one of the four gates in the city's walls. As Lucca has not seen a war since the 1400s, the architecture with the historic center (inside the walls) is well-preserved and features beautiful churches and remains of a Roman amphitheater. If you plan to travel to Tuscany, you should not miss this city.

Discover and visit the Roman Amphitheater, Duomo di San Martino, Torre Guinigi, Torre delle Ore, Palazzo Mansi, Saint Michael's Church, San Frediano's Church, Via Fillungo (main street), Palazzo Pfanner, Piazza Napoleone, Domus Romana, 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.



Book This Package
Flexible Itinerary
Florence
Day 1
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 2
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 3
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 4
Departing from Florence
Transportation to next city by: Regional Air
Assisi
Day 4
Arrive to Assisi
Overnight in Assisi   44 hotels offered
Optional   36 Things to do
Day 5
Overnight in Assisi   44 hotels offered
Optional   36 Things to do
Day 6
Departing from Assisi
Transportation to next city by: Regional Air
Cortona
Day 6
Arrive to Cortona
Overnight in Cortona   10 hotels offered
Day 7
Departing from Cortona
Transportation to next city by: Regional Air
Lucca
Day 7
Arrive to Lucca
Overnight in Lucca   41 hotels offered
Optional   100 Things to do
Day 8
Departing from Lucca
Transportation to next city by: Regional Air
Florence
Day 8
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 9
Departing from Florence
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Florence Hotels (286 total)
›
Assisi Hotels (44 total)
›
Cortona Hotels (10 total)
›
Lucca Hotels (41 total)
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Tours in Florence (1338 total)
›
Tours in Assisi (36 total)
›
Tours in Lucca (100 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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Florence - Umbria - Tuscany 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
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.
Cortona
One of the oldest hill towns in Tuscany, surrounded by 3,000 year old Etruscan walls, Cortona retains much of its history through its architecture. The plain below is speckled with Etruscan tombs, but Cortona isn't just about the past; it is the setting for 'Under the Tuscan Sun' (book and movie), and has a thriving Expat community which is quite involved with the city.

Visit and explore the Accademia Etrusca, Basilica of Saint Margaret of Cortona, Fortress of Girifalco, Diocesan Museum, Piazza della Repubblica, Convento di San Francesco and so much more.
Lucca
Lovely Lucca is one of Tuscany's true gems. This little medieval city is located very close to Pisa, but much more attractive and charming. You enter the historic town via one of the four gates in the city's walls. As Lucca has not seen a war since the 1400s, the architecture with the historic center (inside the walls) is well-preserved and features beautiful churches and remains of a Roman amphitheater. If you plan to travel to Tuscany, you should not miss this city.

Discover and visit the Roman Amphitheater, Duomo di San Martino, Torre Guinigi, Torre delle Ore, Palazzo Mansi, Saint Michael's Church, San Frediano's Church, Via Fillungo (main street), Palazzo Pfanner, Piazza Napoleone, Domus Romana, 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.

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