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Milan - Bologna and San Marino

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9 to 13+ Nights from $1,278*
* Sample price: priced within the past 7 days for a 9/8/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 9 night sample itinerary includes:

  • Flight into Milan and out of Bologna
  • Hotel for 3 nights in Milan
  • Train from Milan to Bologna
  • Hotel for 2 nights in Bologna
  • Rental Car for 4 days
  • Hotel for 3 nights in San Marino
  • Hotel for 1 night in Bologna
  • Driving Time
    Bologna - San Marino: 1 hr. 40 mins. approx.
    San Marino - Bologna: 1 hr. 40 mins. approx.

An unforgettable holiday in Italy and San Marino. Begin your vacation with a visit to Milan (a fashion and shopping capital) and then, catch a train to Bologna (a thriving university town and architectural gem). Finally, pick up your Rental Car for a scenic drive to San Marino (a mountainous microstate located within Italy and one of the world's oldest republics). Drive back to Bologna for a last night stay before returning home.

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
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Flexible Itinerary

  • Milan

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  • Bologna

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  • San Marino City

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  • Bologna

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Italy
San Marino

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Trip Summary

  • Milan
    Milan

    Milan is Italy's window on Europe, its most sophisticated and high-tech metropolis. La Scala, its landmark, is one of Europe's most prestigious opera houses. Milan is one of Europe's top shopping cities, with an incredible concentration of sophisticated, high style boutiques - and that's only fitting because Milan is the dynamo of the Italian fashion industry. Dolce & Gabbana, Ferré, Krizia, Moschino, Prada, Armani, and Versace have all catapulted to international stardom from design studios based here. Inevitably, shopping is of almost religious significance.

    Discover The Last Supper by Michelangelo, The Duomo, Pinacoteca di Brera, Quadrilatero d'Oro, Galleria Vittorio Emanuele II, Scala museum and theatre, Piazza Fontana, Arco della Pace, the churches of Santa Maria delle Grazie and San Lorenzo, Corso Venezia and Piazza San Babila, Sforzesco Castle 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.

  • 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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