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This sample price: priced within the past 7 days for arrival on 7/28/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and 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:
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.
Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 9 nights
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.
2 nights in 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.
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 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.
1 nights in 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.
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.
<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.
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.
*Sample prices on display include ALL taxes & fuel surcharges... read more
close [x] * Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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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. 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 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.
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 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.
From New York City NYC (All Airports) (NY), US for 9 nights
