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Milan - Bologna and San Marino
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9 to 13+ Nigths from $619*
This sample price: priced within the past 7 days for arrival on 1/24/2025. Choose your own arrival dates
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
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). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

This 9 night sample itinerary includes:
  • 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.


Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 9 nights
1269.95 * incl.tax
Related Cities:
Bologna (11)     Milan (74)     San Marino City (6)    
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With Int'l Flight     Without Int'l Flight
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Cabin:
Destination
Arrival date
Stay
1. Milan
  206 hotels
2. Bologna
   (62 hotels)
3. San Marino City
   (14 hotels)
4. Bologna
   (62 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
3 nights in 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. In addition, it's the site of several world-renowned annual trade fairs. 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 and Sforzesco Castle and so much more.



2 nights in Bologna

Bologna is one of the most overlooked gems in Italy, one of the most architecturally unified in Europe - a panorama of sienna-colored buildings, marbled sidewalks, and porticos. Located at the crossroads between Venice and Florence and surrounded by hills, Bologna provides the best of several worlds; it has beautiful piazzas, churches and museums, as well as being a thriving university town, filled with cafes, bars and nightlife. The bars, cafes, and squares fill up with students, and an eclectic mix of concerts, art exhibits, and avant-garde ballet and theater performances always marks the calendar.

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.



3 nights in 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.



1 nights in Bologna

Bologna is one of the most overlooked gems in Italy, one of the most architecturally unified in Europe - a panorama of sienna-colored buildings, marbled sidewalks, and porticos. Located at the crossroads between Venice and Florence and surrounded by hills, Bologna provides the best of several worlds; it has beautiful piazzas, churches and museums, as well as being a thriving university town, filled with cafes, bars and nightlife. The bars, cafes, and squares fill up with students, and an eclectic mix of concerts, art exhibits, and avant-garde ballet and theater performances always marks the calendar.

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.




Book This Package
Flexible Itinerary
Milan
Day 1
Arrive to Milan
Overnight in Milan   206 hotels offered
Optional   378 Things to do
Day 2
Overnight in Milan   206 hotels offered
Optional   378 Things to do
Day 3
Overnight in Milan   206 hotels offered
Optional   378 Things to do
Day 4
Departing from Milan
Transportation to next city by: Train - Milan to Bologna
Bologna
Day 4
Arrive to Bologna
Overnight in Bologna   62 hotels offered
Optional   139 Things to do
Day 5
Overnight in Bologna   62 hotels offered
Optional   139 Things to do
Day 6
Departing from Bologna
Transportation to next city by: Regional Air
San Marino City
Day 6
Arrive to San Marino City
Overnight in San Marino City   14 hotels offered
Optional   8 Things to do
Day 7
Overnight in San Marino City   14 hotels offered
Optional   8 Things to do
Day 8
Overnight in San Marino City   14 hotels offered
Optional   8 Things to do
Day 9
Departing from San Marino City
Transportation to next city by: Regional Air
Bologna
Day 9
Arrive to Bologna
Overnight in Bologna   62 hotels offered
Optional   139 Things to do
Day 10
Departing from Bologna

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Milan Hotels (206 total)
Bologna Hotels (62 total)
San Marino City Hotels (14 total)


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Tours in Milan (378 total)
Tours in Bologna (139 total)
Tours in San Marino City (8 total)


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Package Map Picture
Italy

For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced. Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
San Marino

<b>San Marino</b> is among the smallest countries in the world, only 43 miles in size. More precisely, it is the fifth smallest, but probably the most curious one. This micro-country is a sole survivor of Italy's former (and powerful we must add) city-state network; and it is still holding on as the world's oldest surviving sovereign country and its oldest republic dating back to 301 A.D. Tucked away inside Italy's northeastern region, San Marino is a UNESCO World Heritage Site with lovely things to offer its visitors. You'll find everything from forests, fortress towers, and shopping malls, to medieval markets and Olympic stadiums in this quirky and unique part of the world.
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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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Milan - Bologna and San Marino
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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. In addition, it's the site of several world-renowned annual trade fairs. 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 and Sforzesco Castle and so much more.
Bologna
Bologna is one of the most overlooked gems in Italy, one of the most architecturally unified in Europe - a panorama of sienna-colored buildings, marbled sidewalks, and porticos. Located at the crossroads between Venice and Florence and surrounded by hills, Bologna provides the best of several worlds; it has beautiful piazzas, churches and museums, as well as being a thriving university town, filled with cafes, bars and nightlife. The bars, cafes, and squares fill up with students, and an eclectic mix of concerts, art exhibits, and avant-garde ballet and theater performances always marks the calendar.

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
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.
Bologna
Bologna is one of the most overlooked gems in Italy, one of the most architecturally unified in Europe - a panorama of sienna-colored buildings, marbled sidewalks, and porticos. Located at the crossroads between Venice and Florence and surrounded by hills, Bologna provides the best of several worlds; it has beautiful piazzas, churches and museums, as well as being a thriving university town, filled with cafes, bars and nightlife. The bars, cafes, and squares fill up with students, and an eclectic mix of concerts, art exhibits, and avant-garde ballet and theater performances always marks the calendar.

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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