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Rome - Northern Umbria - San Marino and Bologna (Self Drive)

10 to 15+ Nights from $1,417*
* Sample price: priced within the past 7 days for a 7/29/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 10 night sample itinerary includes:

  • Flight into Rome and out of Bologna
  • Hotel for 3 nights in Rome
  • Rental Car for 7 days
  • Hotels for 3 nights in Northern Umbria
  • Hotel for 2 nights in San Marino
  • Hotel for 2 nights in Bologna
  • Driving Time
    Rome - Northern Umbria: 2 hrs./2 hrs. 30 mins. approx.
    Northern Umbria - San Marino: 2 hrs. /2 hrs. 30 mins. approx.
    San Marino- Bologna: 2 hrs. approx.

Visit Italy`s scenic capital city and three of the stunning cities with a Rental Car!. Begin your vacation in Rome (the Eternal City, with its stunning architecture like the Colosseum and the Roman Forum and delicious food). From here pick up the Rental Car and drive along beautiful landscapes of Italy en route to Northern Umbria (where green is the dominant colour thanks to the hilly terrain and the abundance of water in the region, which is rich in rivers and lakes). Continue to San Marino (a mountainous microstate located within Italy and one of the world's oldest republics) and finish this trip in Bologna (a thriving university town and architectural gem, plus its legendary traditional cuisine). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Rome

    about
  • Northern Umbria

    about
  • San Marino City

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  • Bologna

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San Marino
Italy

Customer Reviews

Trip Summary

  • Rome
    Rome

    Rome is undeniably stunning, from its rich ancient culture, delectable cuisine and coffees to its uniquely European experiences. This city is packed full of sights; with thousands of years of history layered upon itself - you'll find everything from Roman ruins to Renaissance art. It's also home to Vatican City, and sights galore.

    Explore and discover the Roman Colosseum and the Arch of Constantine, discover the Vatican, the smallest independent state in the world; throw a coin in the Trevi Fountain, marvel at the Pantheon, sit on the Spanish Steps, wander the Piazzas, eat the best gelato, climb Palatine Hill, walk the Ancient Appian Way and so much more!

  • Northern Umbria
    Northern Umbria

    Northern Umbria is an exquisite landscape of unblemished nature where olive trees, fields of sunflowers and wildflowers glow under the warmth of the Umbrian sunshine. Perugia, the capital, offers silky chocolates, medieval alleys, and one of Italy's top painting galleries. Just east is one of Italy's spiritual centers, the hill town of Assisi, birthplace of St. Francis. Further north the rocky border city of Gubbio is home to one of Italy's wildest pagan festivals, and Città di Castello contains its own stash of art treasures.

    Visit and explore the amazing Perugia, Assisi, Gubbio and so much more.

  • San Marino City
    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 that is 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.

  • Bologna
    Bologna

    Bologna is one of the most overlooked gems in Italy! Architecturally unified by a panorama of sienna-colored buildings, marbled sidewalks, and porticos it offers beautiful piazzas, churches and museums, as well as quaint cafes, busy bars and vibrant nightlife. It's the perfect destination for experiencing and tasting the region's fabulous food and eponymous pasta sauce. Bologna's university, dating from 1088 is one of the oldest in the world, and continues to thrive and contribute to the city’s successful combination of tradition and innovation.

    Visit and explore the Piazza Maggiore, Saint Petronius Church, Neptune Fountain, Santo Stefano Church, Archaeological Museum, National Gallery, Piazza del Mercato (or market square), Quadrilatero, San Luca Sanctuary, Palazzo Comunale Museum, Museum of History, and so much more.

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