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Southern Tuscany Vacation Packages


The hill towns and valleys south of Siena comprise perhaps Tuscany's most captivating and picturesque region, much of the area is filled with the expansive and beautiful Val d'Orcia. It is a land of medieval castles guarding narrow road passes, isolated farmhouses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a rural setting, and thermal spas dating from long times past. Most of the region has been landscaped over thousands of years, turning the low, rolling hills into farmlands and vineyards that produce Tuscany's mightiest red wines. It offers textbook Italian hill towns, where Roman settlements like Montalcino and Montepulciano grew into medieval cities and today produce two of Italy's top red wines, the powerhouse Brunello di Montalcino and the noble Vino Nobile di Montepulciano. And where the gemlike village of Pienza shelters within its tiny ring of walls a Renaissance core of the most perfect proportions and planning.

Best Southern Tuscany Vacation Packages:

Tuscan Highlights (Self Drive)

7 nights from $1,449*

A unique trip to Italy's Tuscany Region by car! . Discover Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and from there, with Rental Car, main cities in Tuscany, like Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo) and San Gimignano (famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses). 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 Southern Tuscany Vacation Packages:

Map of Southern Tuscany

Southern Tuscany

Hotels

Towns Southern Tuscany

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Regions of Tuscany

  • Chianti Wine Region

    In the center of Tuscany - a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves.

  • 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 Regions of Tuscany

SUGGESTED Southern Tuscany VACATION PACKAGES:

  • Florence and Southern Tuscany (Self Drive)
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  • Enjoy the wonderful Italy and its Southern Tuscany Region!. Delight yourself in 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 Southern Tuscany (boasting the most captivating countryside and vineyards that produce Tuscany's mightiest red wines in cities like: Montepulciano, San Gimignano, Pienza and Volterra). Drive back to Florence for one last night stay, before returning home. 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 Southern Tuscany
    • Hotel for 1 night in Florence
    • Driving Time
      Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
      Southern Tuscany - Florence: 1 hr. /1 hr. 20 mins. approx.



  • Southern Tuscany Getaway
    7 nights from $2,007*
  • Italy! Spend a relaxing vacation in Southern Tuscany and Florence (Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata). Make your home base one of the charming properties 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 hotel and activities.
    Included:
    • Flight into and out of Florence
    • Rent a car for 8 days
    • Hotel for 6 nights in Southern Tuscany
    • Hotel for 1 night in Florence
    • Daily breakfast (if stated in hotel description)


  • Florence and San Gimignano (Self Drive)
    7 nights from $1,583*
  • Explore the beautiful Italy by Car!. 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, continue with your Rental Car and spend a few days at your leisure in San Gimignano (famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form "an unforgettable skyline"). Drive back to Florence for one last stay, before returning home. 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
    • Rent a car for 5 days
    • Hotel for 3 nights in San Gimignano
    • Hotel for 1 night in Florence
    • Driving Time
      Florence - San Gimignano : 1 hr. approx.
      San Gimignano - Florence: 1 hr. approx.



  • Florence and Chianciano Terme (Self Drive)
    7 nights from $1,640*
  • Tuscany`s treasures in Italy!. Visit Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and after that, continue with your Rental Car to Chianciano Terme (one of the best known spa resorts in Tuscany and Italy; a lovely vintage Italian style in the heart of Tuscany). Drive back to Florence for one last stay, before returning home. 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
    • Rent a car for 5 days
    • Hotel for 3 nights in Chianciano Terme
    • Hotel for 1 night in Florence
    • Driving Time
      Florence - Chianciano Terme : 1 hr. 40 mins. approx.
      Chianciano Terme- Florence: 1 hr. 40 mins. approx.



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