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Chianti Wine Region Vacation Packages


Chianti, often considered the 'heart of Tuscany,' is located between Florence, Siena and Arezzo. It's 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. These hills are also the birthplace of one of the world's most famous red wines, the superb Chianti wine. Wine tastings are a must and a pleasure not to be missed when driving along the wine routes in this wonderful region.

Best Chianti Wine Region Vacation Packages:

Florence and The Chianti Wine Region (Self Drive)

7 nights from $1,452*

Discover Italy's most famous wine region by car!. Visit Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). From there, with a Rental Car, leap up 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.

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Other Chianti Wine Region Vacation Packages:

Chianti Wine Region

Chianti Wine Region

Hotels & Activities

Towns in Chianti Wine Region


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Areas of Tuscany

  • Southern Tuscany

    South of Siena - Hill towns, valleys, medieval castles guarding narrow road passes and isolated farmhouses. Perhaps Tuscany`s most captivating and picturesque region.

  • South East Tuscany

    Land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Splendid landscapes with famous monastic settlements, century-old trees and Romanesque parishes.

  • Northwest Tuscany

    Relatively uncrowded between Florence and Pisa - Towns with true architectural beauty and charm: mazes of narrow streets, Romanesque churches and beyond them stretches a land of genteel spas such as Montecatini Terme.

  • Tuscany Coast

    Extensive beaches surrounded by high dunes and fresh pinewoods, characterized by clean water (certified blue flag beaches), interesting villages, and a background of the Apuan Alps.

See All Areas of Tuscany

SUGGESTED Chianti Wine Region VACATION PACKAGES:

  • Rome - Florence - Chianti and Venice
    11 nights from $1,533*
  • Charming Italy Countryside!. Spend a few days visiting Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food) after that, take a train to enjoy Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). From there, pick up the Rental Car, for an enchanting visit to the Chianti Wine Region (beautiful and famous region of Tuscany with best wineries). Drive back Florence to drop the car, and after that, continue by train to ultra-romantic Venice (set on gorgeous canals, intimate Gondola rides under sculpted bridges).

    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
    Included:
    • Flight into Rome and out of Venice
    • Hotel for 3 nights in Rome
    • Train from Rome to Florence
    • Hotel for 2 nights in Florence
    • Rental Car for 4 days
    • Hotel for 3 nights in Chianti Wine Region
    • Hotel for 1 night in Florence
    • Train from Florence to Venice
    • Hotel for 2 nights in Venice
    • Driving Time
      Florence - Chianti Wine Region 1 hr. / 1hr. 30 mins. approx.
      Chianti Wine Region - Florence: 1 hr. / 1hr. 30 mins. approx.



  • Florence and Radda in Chianti (Self Drive)
    7 nights from $1,560*
  • Charming trip to central Tuscany from Italy!. Visit the magnificent city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and after that, rent a car and spend a few days at your leisure in Radda in Chianti (a comune in the Province of Siena in the Italian Tuscany, a beautiful medieval town enclosed in large defensive walls). 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.
    Included:
    • Flight into and out of Florence
    • Hotel for 3 nights in Florence
    • Rental Car for 5 days
    • Hotel for 3 nights in Radda in Chianti
    • Hotel for 1 night in Florence
    • Driving Time
      Florence - Radda in Chianti : 1 hr. 10 mins. approx.
      Radda in Chianti - Florence: 1 hr. 10 mins. approx.



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