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Chianti Getaway (Self Drive)
7 to 10+ Nigths from $1,402*
This sample price: priced within the past 7 days for arrival on 7/17/2025, 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.
Discover one of the most beautiful and famous areas in all Italy!. Make your homebase in Florence and with your Renta Car visit the whole area at your own pace; to the charming Chianti Wine Region (offering a unique landscape, with green, gentle hills covered with wide fields of vineyards and olive groves, small stone villages, characteristic parishes and countryside homes in stone and of course, its worldwide Chianti Wine, made primarily with Sangiovese grapes). Drive back to Florence to drop off the car and finisht this trip with one last night stay. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 7 night sample itinerary includes:
  • Flight into and out of Florence
  • Rental Car for 8 days
  • Hotel for 6 nights in Chianti Wine Region
  • Hotel for 1 night in Florence

  • Driving Time
    Florence - Chianti Wine Region: 50 mins. / 1 hr. 10 mins. approx.
    Chianti Wine Region - Florence: 50 mins. / 1 hr. 10 mins. approx. approx.

Related Itineraries:
Related Cities:
Florence (223)     Chianti Wine Region (11)    
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1. Chianti Wine Region
  51 hotels
2. Florence
   (284 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
6 nights in Chianti Wine Region

Chianti, located in the center of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.

Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni 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
Chianti Wine Region
Day 1
Arrive to Chianti Wine Region
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 2
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 3
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 4
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 5
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 6
Overnight in Chianti Wine Region   51 hotels offered
Optional   38 Things to do
Day 7
Departing from Chianti Wine Region
Transportation to next city by: Regional Air
Florence
Day 7
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1356 Things to do
Day 8
Departing from Florence
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Chianti Wine Region Hotels (51 total)
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Florence Hotels (284 total)
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Tours in Chianti Wine Region (38 total)
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Tours in Florence (1356 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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Chianti Getaway (Self Drive)
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Chianti Wine Region
Chianti, located in the center of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.

Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni 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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