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San Marino - South East Tuscany and Florence (Self Drive)

9 to 13+ Nights from $1,122*
* This sample price: priced within the past 7 days for arrival on 2/16/2024, 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
  • Rent a car for 7 days.Pick Up: Bologna Airport/Drop Off: Florence Downtown
  • Hotel for 3 nights in San Marino
  • Hotel for 3 nights in South East Tuscany
  • Hotel for 3 nights in Florence
  • Driving Time
    Bologna Airport - San Marino: 1 hr. 35 mins. approx.
    San Marino - South East Tuscany Area: 2 hrs 20 /40 mins. approx.
    South East Tuscany - Florence: 1 hr. 20 -50 mins. approx.

San Marino and Italian Tuscany!. Enjoy the captivating countryside as you drive to San Marino, a mountainous microstate located within Italy and one of the world’s oldest republics, then South East Tuscany and finally, the magnificent 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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Arrival date
(14 hotels)
(46 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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Going To:
Staying For:
San Marino City
South East Tuscany

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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.

  • South East Tuscany

    South East Tuscany is a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Snowy-white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. Splendid landscapes where you can find famous monastic settlements, completely surrounded by century-old trees and numerous Romanesque parishes. This is the area where the humanist Renaissance of Florence meets and melds with the intangible, hazy spirituality of Umbria`s green hills. Nearby: Arezzo, Cortona, Anghiari, Monterchi , Sansepolcro and the beautiful castle of Poppi - these are just some of the most beautiful towns in South East Tuscany, waiting to be discovered on your Tuscan trip. Distances: Florence-Arezzo - 50 miles, Siena-Arezzo - 57 miles , Arezzo-Cortona - 19 miles, Florence-Cortona - 64 miles, Siena-Cortona - 45 miles

  • 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!