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Tuscany And Hill Towns: Point of Interest Map
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Tuscany and Hill Towns Vacation Packages


Tuscany isn’t just famous for one thing, but multiple. Famed for an endless list of exceptional features, from glorious landscapes, vast history, delicious cuisines, to even artistic legacy. Tuscany one of the most popular travel destinations in the world, offering a smorgasbord of cities and small villages scattered about the lush greenery. In the thousands of years of Tuscany’s lifetime, there has been a multitude of art periods. All of which have a fascinating history and significance of the country’s culture. These include the Etruscan, Roman, Middle Ages, Romanesque, Gothic, and Baroque, but by far Tuscany’s most famous art style was its Renaissance period.

Best Vacation Packages:

Areas of Tuscany


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Regions of Italy

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SUGGESTED ITINERARIES

  • Tuscan Adventure Self Drive (Florence - Montecatini - Lucca - Florence)
    7 nights from $1,293*
  • Tuscany Road Trip in Italy!. Visit the magnificent Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), and from there, with a Rental Car, leap up to Tuscany Region, visiting Montecatini Terme (known for the art nouveau architecture, the Parco delle Terme Spa Complex) and Lucca (fantastic medieval city walls that still encircle most of the historic old town and its cobblestone streets). 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 Montecatini
    • Hotel for 2 night in Lucca
    • Hotel for 1 night in Florence
    • Driving Time
      Florence - Montecatini: 1 hr. 10 mins. approx.
      Montecatini - Lucca: 40 mins. approx.
      Lucca - Florence: 1 hr. 30 mins. approx.



  • Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)
    9 nights from $1,622*
  • Focus your visit to Italy in wonderful Tuscany!. Visit artistic Florence, then pick up your car and spend some leisurely days staying in Lucca, San Gimignano and Siena to be able to experience all the different aspects of this charming region. Return to Florence for one last 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 Lucca
    • Hotel for 2 nights in San Gimignano
    • Hotel for 2 nights in Siena
    • Hotel for 1 night in Florence


  • 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.



  • Florence - Siena - Assisi - Rome by Train
    8 nights from $1,394*
  • Explore Italy!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Siena (famous for its cuisine, art, museums, medieval cityscape and Piazza del Campo) and to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills). Finish with a stay in imperial Rome (the Eternal City, with its stunning Colosseum, Roman Forum and delicious food), all with the ease of travelling by train.

    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 Rome
    • Hotel for 2 nights in Florence
    • Train from Florence to Siena
    • Hotel for 2 nights in Siena
    • Train from Siena to Assisi
    • Hotel for 2 nights Assisi
    • Train from Assisi to Rome
    • Hotel for 2 nights Rome


  • Tuscan Highlights Self Drive (Florence - Siena - San Gimignano)
    7 nights from $1,385*
  • 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.



  • Rome - Siena - Florence - Venice by Train
    8 nights from $1,055*
  • Combine glorious cities in Italy with this fun vacation!. Visit Rome (the Eternal City, with its stunning Colosseum, Roman Forum and delicious food) after that, travel to Siena (representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and next, to Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture). Finally, visit Venice (set on gorgeous canals, intimate Gondola rides under sculpted bridges). Travel between each city by train.

    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 Siena
    • Hotel for 1 night in Siena
    • Train from Siena to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Venice
    • Hotel for 2 nights in Venice


  • Florence - Lucca - Venice by Train
    7 nights from $1,975*
  • Enjoy three beautiful and exciting destinations across Italy!. Visit artistic Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), Lucca (fantastic medieval city walls that still encircle most of the historic old town) and romantic Venice (set on gorgeous canals, intimate Gondola rides under sculpted bridges), all with the ease of travelling by train.

    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 Venice
    • Hotel for 3 nights in Florence
    • Train from Florence to Lucca
    • Hotel for 2 nights in Lucca
    • Train from Lucca to Venice
    • Hotel for 2 nights in Venice


  • Tuscan Scenery Self Drive (Florence - Siena - Pisa - Lucca)
    6 nights from $1,426*
  • A perfect introduction to Italy`s Tuscany Region by Car!. Visit Florence (home to Renaissance art and architecture) and after that, drive along these charming cities in the Tucany Region, like: Siena (famous for its horse race held twice a year in Piazza del Campo), Pisa (world-renowned Leaning Tower of Pisa) and Lucca (fantastic medieval city walls and its cobblestone streets). 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 5 days
    • Hotel for 1 night in Siena
    • Hotel for 1 night in Pisa
    • Hotel for 1 night in Lucca
    • Hotel for 1 night in Florence
    • Driving Time
      Florence -Siena: 1 hr. 15 mins. approx.
      Siena - Pisa: 1 hr. 40 mins. approx.
      Pisa - Lucca: 40 mins. approx.
      Lucca - Florence: 1 hr. 20 mins. approx.



  • Rail to Road: Genoa - Cinque Terre - Florence - Chianti - Rome
    11 nights from $2,221*
  • Explore the beautifulItaly! Start in Genoa (ancient Renaissance buildings, famous museums and very good restaurants), then catch a train to;Cinque Terre (five miles of rocky coast with five small villages overlooking the sea, in the midst of two capes with hundreds of miles of beautiful paths); continue by train to Florence (Michelangelo's David, Botticelli's Birth of Venus, and Raphael's La Velata). After your visit, pick up your car and drive to the Chianti Wine Region (charming hill-covered region with picturesque landscape of small stone villages, sprawling vineyards and olive groves.) and finally drive to Rome (Italy's treasure with two millennia of artistic achievement).


    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 Genoa and out of Rome
    • Hotel for 2 nights in Genoa
    • Train from Genoa to La Spezia (Entry to Cinque Terre)
    • Hotel for 2 nights in La Spezia
    • Train from La Spezia to Florence
    • Hotel for 2 nights in Florence
    • Rental Car for 3 days
    • Hotel for 2 nights in Chianti
    • Hotel for 3 nights in Rome


  • Florence - San Gimignano - Rome (Self Drive)
    9 nights from $2,078*
  • A Self Drive Vacation to some of our most popular destinations in Italy!. Spend a few days in artistic Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), then pick up your Rental Car and drive for a visit to San Gimignano (famous for its medieval architecture and towers). Finish with a stay in monumental Rome (the Eternal City, with its stunning Colosseum, Roman Forum and delicious food).

    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 Rome
    • Hotel for 3 nights in Florence
    • Rental Car for 4 days
    • Hotel for 3 nights in San Gimignano
    • Hotel for 3 nights in Rome
    • Driving Time
      Florence - San Gimignano: 1 hr. 10 mins. approx.
      San Gimignano - Rome: 3 hrs. 20 mins. approx.



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  • Tuscan Wine & Cuisine

    Whether you are a wine enthusiast, a culinary traveler, or a lover of art and history, Tuscany offers one of the most rewarding journeys in Italy.

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