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Siena Getaway (Self Drive)
1 Customer Feedbacks
7 to 10+ Nigths from $1,088*
This sample price: priced within the past 7 days for arrival on 8/14/2025, departure from Boston BOS (MA), US. Choose your own departure city, cabin type and dates.
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1 Customer Feedbacks It was so easy to plan our trip with you. The hotels were both friendly and professional. ... more
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.
Spend a relaxing vacation in the Italian Tuscany. Make Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops); your home base in this area and use your rent a car to visit the whole area at your own pace. This is a flexible vacation package. Select your number of nights in each city, desired hotels and activities.
This 7 night sample itinerary includes:
  • Flight into and out of Florence
  • Rental Car for 8 days
  • Hotel for 6 nights in Siena
  • Hotel for 1 night in Florence
Price history for this itinerary (past 7 days):
From Boston BOS (MA), US for 7 nights
1087.92 * incl.tax
From New York City NYC (All Airports) (NY), US for 7 nights
1198.11 * incl.tax
Related Itineraries:
Related Cities:
Florence (223)     Siena (26)    
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With Int'l Flight     Without Int'l Flight
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Destination
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Stay
1. Siena
  43 hotels
2. Florence
   (284 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
6 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.



Book This Package
Flexible Itinerary
Siena
Day 1
Arrive to Siena
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 2
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 3
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 4
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 5
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 6
Overnight in Siena   43 hotels offered
Optional   99 Things to do
Day 7
Departing from Siena
Transportation to next city by: Regional Air
Florence
Day 7
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1348 Things to do
Day 8
Departing from Florence
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Siena Hotels (43 total)
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Florence Hotels (284 total)
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Tours in Siena (99 total)
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Tours in Florence (1348 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.
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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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*Sample prices on display include ALL taxes & fuel surcharges... read more
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Siena Getaway (Self Drive)
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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.
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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