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Siena Vacation Packages


Siena is a beautiful medieval city with a UNESCO-listed historic center. Surrounded by a well-preserved 1,000-year-old wall, it's best known for its stunning cathedral and the Palio horse race, which takes place twice yearly in its large square, Piazza Del Campo. In addition to its Duomo and charming old town, the city offers winding medieval alleyways, delicious food and wine, museums, and breathtaking views of the Tuscan countryside.

Best Siena Vacation Packages:

Rome - Siena - Florence - Venice by Train

8 nights from $1,100*

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

113 Customer Reviews

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Other Siena Vacation Packages:

Siena

Siena

Hotels & Activities

Travel Guide

  • Discover Siena

    Siena is a beautiful medieval city with a UNESCO listed historic center. Surrounded by a well-preserved 1,000-year-old wall, it's best known for its stunning cathedral and the Palio horse race, which takes place twice yearly in its large square, Piazza Del Campo. In addition to its Duomo and charming old town, the city offers winding medieval alleyways, delicious food and wine, museums, and breathtaking views of the Tuscan countryside.

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.

  • 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 Areas of Tuscany

Regions of Italy

See All Regions of Italy

SUGGESTED Siena VACATION PACKAGES:

  • The Best of Rome - Siena - Florence - Venice
    15 nights from $3,117*
  • Most visited cities in Italy!. Explore Rome`s (the Eternal City) monuments, The Vatican and enjoy a evening food, after that, travel to Siena (a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) where to have a Cooking Class, and next, to Florence (capital of Italy’s Tuscany region), there have a Night Tour and visits to The Uffizi and Accademia, The Cathedral and a taste of its delicious food. Finally, visit Venice (set on gorgeous canals, intimate Gondola rides and under sculpted bridges), where to enjoy a Canal Cruise, a Doge`s Palace Visit and a delicious Food and Wine Tasting.

    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 4 nights in Rome
    • Train from Rome to Siena
    • Hotel for 3 night in Siena
    • Train from Siena to Florence
    • Hotel for 4 nights in Florence
    • Train from Florence to Venice
    • Hotel for 4 nights in Venice

      Sample of Included Tours:
    • Guided City Tour in Rome
    • Colosseum, Palatine Hill and Roman Forum Tour in Rome
    • City Evening Food Tour around Rome
    • Vatican Museums and Sistine Chapel Tour from Rome
    • Guided City Tour in Siena
    • Italian Cooking Class in Siena
    • Night Time City Tour in Florence
    • Visit Uffizi and Accademia Museums in Florence
    • Food and Markets Tour around Florence
    • Visit to Florence Cathedral
    • Night Tour of Venice
    • Canal Cruise around Venice
    • Food and Wine Tastings around Venice
    • Visit to Doge`s Palace and St Mark`s Basilica in Venice

      Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.


  • Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)
    10 nights from $2,014*
  • Delight yourself in the charming Tuscany Region, during your vacations in Italy!. From Pisa (world-renowned Leaning Tower of Pisa), drive along the Tuscany visiting San Gimignano (medieval architecture, unique in the preservation of about a dozen of its tower houses) after that, Siena (medieval cityscape and the Palio, a horse race held in Piazza del Campo) and up to Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture). From there, catch a train to the fabulous Rome (the Eternal City, with the 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 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.



  • Rome - Siena - Florence - Bologna - Milan - Verona - Padua - Venice (Self Drive)
    12 nights from $2,293*
  • A fantastic chance to visit main cities of Italy in a Car!. Begin with a stay in Rome (the Eternal City, with 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).

    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
    • 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.



  • Tuscan Scenery Self Drive (Florence - Siena - Pisa - Lucca)
    6 nights from $896*
  • 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.



  • Journey through Tuscany and Umbria Self Drive(Rome - Siena - Pisa - Florence - Assisi)
    8 nights from $1,382*
  • 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.

    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 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


  • Rail to Road: Florence - Siena - Rome - Sorrento - Naples
    More details
  • Lovely Italy!. 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.

    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
    • Train from Florence to Siena
    • Hotel for 2 nights in Siena
    • Train from Siena to Rome
    • Hotel for 3 nights in Rome
    • Rental Car for 5 days
    • Hotel for 3 nights in Sorrento
    • Hotel for 1 night in Naples


  • Rome - Siena - Florence - Venice for Foodies
    15 nights from $3,079*
  • Get a taste of Italy!. During this trip visiting Rome (the Eternal City, with its stunning architecture), Siena (representing a quaint medieval time with gothic palaces and Tuscan altarpieces), Florence (capital of Italy’s Tuscany region) and Venice (gorgeous canals and intimate Gondola rides under sculpted bridges), discover all their flavors... from best street food and markets, to learn to make your own pizza to sampling favorite sweets and coffees and unforgettable Dining Experiences in these italian destinations!.

    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 4 nights in Rome
    • Train from Rome to Siena via Florence
    • Hotel for 3 nights in Siena
    • Train from Siena to Florence
    • Hotel for 4 nights in Florence
    • Train from Florence to Venice
    • Hotel for 4 nights in Venice

      Sample of Included Tours:
    • City Food Tour around Rome
    • Pizza Making Class in Rome
    • Sweet Eats Tour around Rome
    • Dinner In Rome
    • Italian Cooking Class in Siena
    • Day Trip to Tuscan Winery from Siena
    • Food and Markets Tour around Florence
    • Italian Cooking Class in Florence
    • Dinner Experience in Florence
    • Food Tasting Tour around Venice
    • Rialto Market Food Tour in Venice
    • Italian Dining Experience in Venice

      Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.


  • San Marino - Siena - Florence (Self Drive)
    9 nights from $1,002*
  • San Marino and Italian Tuscany!. Behold the beautiful natural landscape as you drive to San Marino (a mountainous microstate located within Italy and one of the world's oldest republics), then continue to medieval Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo) and finally the artistic city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture).

    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 Bologna and out of Florence
    • Rental Car for 7 days.Pick Up: Bologna Airport/Drop Off: Florence Downtown
    • Hotel for 3 nights in San Marino
    • Hotel for 3 nights in Siena
    • Hotel for 3 nights in Florence
    • Driving Time
      Bologna Airport - San Marino: 1 hr. 35 mins. approx.
      San Marino - Siena: 3 hrs. approx.
      Siena - Florence: 1 hr. 10 mins. approx.



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