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Florence and Southern Tuscany with Signature Transfers
7 to 10+ Nigths from $2,381*
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.
Southern Tuscany Getaway!. From Florence (capital of Tuscany; home to Renaissance Art and Architecture), travel Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo). After that, have a pleasant stay at Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries). Finally, get back for one last night stay in Florence. Along your way, by door-to-door service between these destinations discover: medievals Monteriggioni and San Gimignano (famous towers and wine); Montepulciano and Lucignano.

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This 7 night sample itinerary includes:
  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Transfer from Hotel in Florence to Hotel in Siena via Monteriggioni and San Gimignano
  • Hotel for 2 nights in Siena
  • Transfer from Hotel in Siena to Hotel in Cortona via Montepulciano
  • Hotel for 1 night in Cortona
  • Transfer from Hotel in Cortona to Hotel in Florence via Lucignano
  • Hotel for 1 night in Florence
Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 7 nights
2380.18 * incl.tax
Related Itineraries:
Related Cities:
Florence (230)     Siena (29)     San Gimignano (13)     Cortona (3)     Monteriggioni (3)     Montepulciano (3)    
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Cabin:
Destination
Arrival date
Stay
1. Florence
  286 hotels
2. Siena
   (43 hotels)
3. Cortona
   (10 hotels)
4. Florence
   (286 hotels)
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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 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 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 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
Siena
Day 4
Arrive to Siena
Overnight in Siena   43 hotels offered
Optional   97 Things to do
Day 5
Overnight in Siena   43 hotels offered
Optional   97 Things to do
Day 6
Departing from Siena
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
Florence
Day 7
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 8
Departing from Florence
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Florence Hotels (286 total)
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Siena Hotels (43 total)
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Cortona Hotels (10 total)
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Tours in Florence (1338 total)
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Tours in Siena (97 total)
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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):

Your Preferred Major Airport:

*Sample prices on display include ALL taxes & fuel surcharges... read more
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Florence and Southern Tuscany with Signature Transfers
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Map
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.
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.
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.
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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