Southern Tuscany Vacation Packages

The hill towns and valleys south of Siena comprise what is perhaps Tuscany's most captivating and picturesque region, the expansive and beautiful Val d'Orcia. It is a land of medieval castles guarding narrow passes, isolated farm houses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a bucolic setting, and thermal spas dating from times long ago. 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 postcard perfect 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.

Other Southern Tuscany Vacation Packages:

A unique trip to Italy's Tuscany Region by car! . Discover Florence (capital of Italy’s Tuscany region, home to 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 horse race 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.

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 and out of Florence

Hotel for 2 nights in Florence

Rental Car for 6 days

Hotel for 2 nights in Siena

Hotel for 2 nights in San Gimignano

Hotel for 1 night in Florence

Driving Time
Florence - Siena: 1 hr. 10 mins. approx.
Siena - San Gimignano: 1 hr. approx.
San Gimignano - Florence: 1 hr. 15 mins. approx.

7 nights from $1,615*

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Enchanting landscapes, magical hilltop hamlets and vineyars in The Southern Tuscany, in addition to cities with rich history in Italy. Start in Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food), after that, catch a train to Florence (Italy’s Tuscany region, is home to Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (captivating countryside and vineyards that produce Tuscany's mightiest red wines in cities like: Montepulciano, San Gimignano, Pienza and Volterra). Drive back to Florence to drop off the car and finisht this trip, travelling by train to 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 nights

Hotel for 3 nights in Southern Tuscany

Hotel for 1 night in Florence

Train from Florence to Venice

Hotel for 2 nights in Venice

Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Florence: 1 hr. /1 hr. 20 mins. approx.

11 nights from $2,536*

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Visit two of Italy`s most charming regions with a Rental Car!. Start in Florence (capital of Italy’s Tuscany region, is home to 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) and after that, to Sorrento (with more than two-thirds the year spent drenched in sunshine) in the Neapolitan Riviera. Finish this trip, driving to Naples to drop off the car and to catch your flight back home.

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 Florence and out of Naples

Hotel for 3 nights in Florence

Rental Car for 8 days

Hotel for 3 nights in Southern Tuscany

Hotel for 3 nights in Sorrento

Hotel for 1 night in Naples

Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Sorrento: 5 hrs. 30 mins. approx.
Sorrento - Naples: 1 hr. 10 mins. approx.

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Main cities and the pinturesque Tuscany in Italy!. Start in Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food), after that, continue by train to Florence (capital of Italy’s Tuscany region, is home to 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 to drop off the car and finisht this trip with one last night stay.

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 Florence

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 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.

9 nights from $1,712*

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Areas 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.

SUGGESTED Southern Tuscany VACATION PACKAGES:

• 
  Florence - Southern Tuscany - Positano (Self Drive)
  10 nights from $2,018*
  ›
Visit Italy`s charming regions, with this holiday package!. From Florence (capital of Italy’s Tuscany region, home to many masterpieces of Renaissance art and architecture); pick up the Rental Car and drive along the beautiful Southern Tuscany (renowned as one of the world's best wine regions, like Chianti, with its hilltop towns and lush landscapes, delicious dishes and art). From there, drive down the south to Amalfi Coast (with its breathtaking views, famous for its cuisine and its production of limoncello liqueur), until your next destination; Positano (a picturesque beach town with splendid coastline; famous for its colorful buildings, excellent restaurants, and mild climate). Finish this trip, driving to Naples (known for its natural beauties, home place of Pizza and Vesuvius Mount) for one last stay before returning home!.

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 Florence and out of Naples
• Hotel for 3 nights in Florence
• Rental Car for 8 days
• Hotel for 3 nights in Southern Tuscany
• Hotel for 3 nights in Positano
• Hotel for 1 night in Naples

• Driving Time
  Florence - Southern Tuscany Area: 1 hr. 10 - 50 mins. approx.
  Southern Tuscany - Positano: 5 hrs. 10 - 55 mins. approx.
  Positano - Naples: 1 hr. 20 mins. approx.
  
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• 
  Florence and Southern Tuscany (Self Drive)
  7 nights from $1,566*
  ›
Enjoy the wonderful Italian 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.

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 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.
  
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• 
  Southern Tuscany Getaway
  7 nights from $1,310*
  ›
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.

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 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)
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• 
  Florence and San Gimignano (Self Drive)
  7 nights from $1,697*
  ›
Explore the beautiful cities in 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.

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 and out of Florence
• Hotel for 3 nights in Florence
• Rental 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.
  
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• 
  Florence and Chianciano Terme (Self Drive)
  7 nights from $1,677*
  ›
Tuscany`s treasures in Italy!. Visit Florence (capital of Italy’s Tuscany region, home to 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). Drive back to Florence for one last stay, before returning home.

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 and out of Florence
• Hotel for 3 nights in Florence
• Rental 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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