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San Marino - Siena and Florence (Self Drive)

9 to 13+ Nights from $1,062*
* This sample price: priced within the past 7 days for arrival on 2/11/2024, departure from New York City (All Airports) (NY), US. Choose your own departure city and dates.

This 9 night sample itinerary includes:

  • Flight into Bologna and out of Florence
  • Reantal 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.

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). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

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(14 hotels)
(42 hotels)
(232 hotels)

Please contact us for any special arrangements such as more than three rooms and partial stays.

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Flexible Itinerary

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Trip Summary

  • San Marino City

    Only 43 miles in size, the little Republic of San Marino is independent, with its own government and laws even though it is entirely surrounded by Italy. The world`s oldest sovereign state, it dates from 301 AD. Atop the center of this hilly area`s highest point, Mount Titano, is the capital city of San Marino. Medieval stone walls surround the original settlement, built entirely of stone and completely pedestrianized. The three fortresses at the top of the mountain give San Marino its best-known image and are linked by a path that runs along the entire ridge of the mountain. Visit and explore the Piazza Dalla Liberta (the most popular public square); Palazzo Pubblico (Town Hall and where you'll find the changing of the guards); Towers of San Marino (Guaita, Cesta, and Montale); Mount Titano and the several small and so much more.

  • Siena

    The beautiful town of Siena is the largest of hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces. Recommended Stay: At least 3 nights Must See`s: Cathedral of Santa Maria Assunta; Piazza del Campo; Palazzo Pubblico; Torre del Mangia; Biblioteca Piccolomini; Siena National Gallery; Church of San Domenico; Piazza Salimbeni; Porta Pispini; Siena Civic Museum and so much more!

  • Florence

    The Italian city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and of course incredible gastronomy, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world. The most popular and important sites in Florence include the Cathedral, the Baptistery, the Uffizi, the Bargello, and the Accademia. Spend a day at the Boboli Gardens or climb the hill to the church of San Miniato al Monte to experience an enchanting view of Florence, Italy. Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more!