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Siena Vacation Packages


Best known for it`s UNESCO listed walled town center, winding medieval alleyways, and Palio, a historic horse race that takes place twice during the summer months. Siena is the perfect location to get away from the hustle and bustle. It is a nice combination of food, wine, museums and scenery. Moreover, Siena is an eminent medieval city with a UNESCO-listed historic center. Surrounded by a well-preserved 1,000-year-old wall, it's best known for hosting the Palio horserace, which takes place twice yearly, as well as plenty of medieval masterpieces all over the place.

Best Siena Vacation Packages:

A Stay in Siena

7 nights from $1,553*

Spend a relaxing vacation in Tuscany. Make Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops); your home base 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 hotels and activities.

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Other Siena Vacation Packages:

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Siena

Hotels and Activities

Regions of Italy

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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.

  • 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.

See Regions of Tuscany

SUGGESTED Siena VACATION PACKAGES:

  • Florence - Siena - Pisa - Lucca by Train
    6 nights from $2,056*
  • The Tuscan region of Italy is extremely famous, for its sunshine, friendly people, stunning vistas, food and wine. Explore the absolute best of this area with visits to Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture), then Siena, continue to Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural wonders) and Lucca (known throughout Italy for its fantastic medieval city walls that still encircle most of the historic old town). Finally enjoy a last night stay in Florence before returning home. All these destinations are connected by train. 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 2 nights in Florence
    • Train from Florence and Siena
    • Hotel for 1 night in Siena
    • Train from Siena and Pisa (via Empoli)
    • Hotel for 1 night in Pisa
    • Train from Pisa and Lucca
    • Hotel for 1 night in Lucca
    • Train from Lucca and Florence
    • Hotel for 1 night in Florence


  • Rome - Siena - Florence - Venice by Train
    8 nights from $1,489*
  • Combine glorious cities in Italy with this fun vacation!. Visit Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food) after that, travel to Siena (a region halted in time, 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 many masterpieces of Renaissance art and architecture). Finally, visit Venice (set on gorgeous canals, intimate Gondola rides will guide you past sumptuous palaces and under sculpted bridges). Travel between each city by train. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    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


  • Rome - Siena - Florence by Train
    8 nights from $1,913*
  • Astound yourself visiting these cities in Italy!. Start in Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food) then, travel to Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and finally, to Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). Transportation between cities are by train. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Rome and out of Venice
    • Hotel for 3 nights in Rome
    • Train from Rome to Siena
    • Hotel for 2 night in Siena
    • Train from Siena to Florence
    • Hotel for 3 nights in Florence


  • Tuscan Highlights (Self Drive)
    7 nights from $1,743*
  • 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.
    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.



  • Tuscan Scenery (Self Drive)
    6 nights from $2,126*
  • A perfect introduction to Italy`s Tuscany Region by Car!. Visit Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and after that, drive along these charming cities in the Tucany Region, like: Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo), Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural wonders) and Lucca (known throughout Italy for its 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. 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 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.



  • Beautiful Tuscany (Self Drive)
    9 nights from $1,936*
  • 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. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Florence and out of Florence
    • Hotel for 2 nights in Florence
    • Rent a 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
    • Daily breakfast (if stated in hotel info)


  • Rome - Tuscany - The Veneto - Lake Como - Milan by Train
    13 nights from $2,180*
  • Sample Italy with this unique, customizable vacation package!. Travel by train between all these cities; begining in Rome (the eternal city). From there the train will allow to admire the beautiful tuscany countryside and its main cities, like: Siena (a distinctively medieval atmosphere, time has stood still in this quaint city), Pisa (famous for its Leaning Tower) and Florence (an art lovers dream!. See works by Raphael, Michelangelo and Botticelli). Continue to Verona (a charming Renaissance city, famous as home to star-crossed lovers Romeo and Juliet) in the Veneto Area, and after that, to Venice (romance and magic flow through this canal city). Finally, visit Lake Como (Italy`s most famous lake and home to international celebrities) and Milan (a world fashion capital). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Rome and out of Milan
    • Hotel for 2 nights in Rome
    • Train from Rome to Siena
    • Hotel for 1 night in Siena
    • Train from Siena to Pisa
    • Hotel for 1 night in Pisa
    • Train from Pisa to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Verona
    • Hotel for 1 night in Verona
    • Train from Verona to Venice
    • Hotel for 2 nights in Venice
    • Train from Venice to Lake Como
    • Hotel for 2 nights in Lake Como
    • Train from Lake Como to Milan
    • Hotel for 2 nights in Milan


  • Rome - Siena - Pisa - Florence - Verona - Venice by Train
    9 nights from $1,322*
  • A fantastic highlights of Italy travelling by train!. Discover Rome (the Eternal City) then, travel to Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and next, to Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural wonders). Continue to Florence (home to many masterpieces of Renaissance art and architecture in the Tuscany) after that, Verona (known as one of the most romantic cities in Italy) and finally, Venice (set on gorgeous canals and intimate Gondola rides). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Rome and out of Venice
    • Hotel for 2 nights in Rome
    • Train from Rome to Siena
    • Hotel for 1 night in Siena
    • Train from Siena to Pisa
    • Hotel for 1 night in Pisa
    • Train from Pisa to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Verona
    • Hotel for 1 night in Verona
    • Train from Verona to Venice
    • Hotel for 2 nights in Venice


  • A Stay in Siena
    7 nights from $1,553*
  • Spend a relaxing vacation in Tuscany. Make Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops); your home base 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 hotels and activities.
    Included:
    • Flight into and out of Florence
    • Rent a car for 8 days
    • Hotel for 6 nights in Siena
    • Hotel for 1 night in Florence
    • Daily breakfast (if stated in hotel description)


  • Journey through Tuscany and Umbria
    8 nights from $1,870*
  • Combine several of the most popular cities in Italy! Rome (Italy`s treasure with two millennia of artistic achievement), Siena, Pisa (a city in Italy's Tuscany region best known for its iconic Leaning Tower), Florence (Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata) and Assisi with a rent a car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • International Flight into and out of Rome
    • Hotel for 2 nights in Rome
    • Rent a car for 7 days
    • Hotel for 1 nights in Siena
    • Hotel for 1 night in Pisa
    • Hotel for 2 nights in Florence
    • Hotel for 1 night in Assisi
    • Hotel for 1 night in Rome


  • Italian Discovery
    12 nights from $2,728*
  • Begin your trip in Florence, catch a train for a visit to Siena (Southern Tuscany), then another train to Rome. At the end of your stay in Rome, pick up your rent a car for a drive to Sorrento (Amalfi Coast) and end with a night in Naples. This is a flexible package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Hotel for 3 nights in Florence
    • Train: Florence - Siena
    • Hotel for 2 nights in Siena
    • Train: Siena - Rome
    • Hotel for 3 nights in Rome
    • Rent a car for 5 days
    • Hotel for 3 nights in Sorrento
    • Hotel for 1 night in Naples


  • Highlights of Italy (Self Drive)
    12 nights from $1,775*
  • A fantastic chance to visit main cities of Italy, in this Self-Drive vacation package!. Begin with a stay in Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food) and after that, with your Rental Car, drive along the country visiting: Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio), Florence (home to many masterpieces of Renaissance art and architecture, Bologna (thriving university town and architectural gem, plus its legendary traditional cuisine), Milan (one of the fashion and high-tech capitals of the world), Verona (charming Renaissance city, famous as home to star-crossed lovers Romeo and Juliet), Padova/Padua (beautiful historical centre and charming architecture) and Venice (set on gorgeous canals, intimate Gondola rides will guide you past sumptuous palaces and under sculpted bridges). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Rome and out of Venice
    • Hotel for 3 nights in Rome
    • Rental Car for 10 days
    • Hotel for 1 night in Siena
    • Hotel for 2 nights in Florence
    • Hotel for 1 night in Bologna
    • Hotel for 1 night in Milan
    • Hotel for 1 night in Verona
    • Hotel for 1 night in Padua (Padova)
    • Hotel for 2 nights in Venice
    • Driving Time
      Rome - Siena: 2 hrs. 50 mins. approx.
      Siena - Florence: 2 hrs. approx.
      Florence - Bologna: 1 hr. 45 mins. approx.
      Bologna - Milan: 2 hrs. 30 mins. approx.
      Milan - Verona: 2 hrs. 15 mins. approx.
      Verona - Padua: 1 hr. 55 mins. approx.
      Padua - Venice: 45 mins. approx.



  • Rome - Siena - Florence - Venice - Verona - Milan by Train
    12 nights from $2,140*
  • Discover Italy`s greatest cities by train!. Start in Rome (the Eternal City) then, travel to Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and next, Florence (home to many masterpieces of Renaissance art and architecture). Continue to Venice (set on gorgeous canals and intimate Gondola rides), up next is Verona (known as one of the most romantic cities in Italy) and lastly, Milan (one of the fashion and high-tech capitals of the world; known for the majestic Duomo Cathedral and the dazzling Vittorio Emanuele II shopping arcade). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Hotel for 2 nights in Rome
    • Train from Rome to Siena
    • Hotel for 2 nights in Siena
    • Train from Siena to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Venice
    • Hotel for 2 nights in Venice
    • Train from Venice to Verona
    • Hotel for 2 nights in Verona
    • Train from Verona to Milan
    • Hotel for 2 nights in Milan


  • Heaven on Earth - Italy and Switzerland
    12 nights from $1,780*
  • This Heavenly vacation package is a must-do list of all of the most idyllic cities that Italy and Switzerland offer. Combine Imperial Rome and all its treasures, artistic Florence, sunny Siena in the south of Tuscany, charming and sumptuous Venice, breathtaking Lucerne and Zurich with ES, TRN, EC and IR Trains. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Rome and out of Zurich
    • Hotel for 2 nights in Rome
    • Train from Rome to Florence
    • Hotel for 2 nights in Florence
    • Train from Florence to Siena
    • Hotel for 2 nights in Siena
    • Train from Siena to Venice
    • Hotel for 2 nights in Venice
    • Train from Venice to Lucerne
    • Hotel for 2 nights in Lucerne
    • Train from Lucerne to Zurich
    • Hotel for 2 nights in Zurich


  • Tuscan Journey
    10 nights from $2,313*
  • Delight yourself in the charming Tuscany Region, during your vacations in Italy!. From Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural wonders), drive along the Tuscany visiting San Gimignano (famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses) after that, Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo) and up to Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). From there, catch a train to the fabulous Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Pisa and out of Rome
    • Rental Car for 9 days
    • Hotel for 2 nights in Pisa
    • Hotel for 2 nights in San Gimignano
    • Hotel for 2 nights in Siena
    • Hotel for 2 nights in Florence
    • Train from Florence to Rome
    • Hotel for 2 nights in Rome
    • Driving Time
      Pisa- San Gimignano: 1 hr. 25 mins. approx.
      San Gimignano - Siena: 50 mins. approx.
      Siena - Florence: 1 hr. 45 mins. approx.



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