Europeandestinations.com is Tripmasters.com now. Ownership, management, and activity remain the same. All existing bookings will be serviced as always.
Rome - Northern Umbria - San Marino and Bologna (Self Drive)
10 to 15+ Nigthsfrom $1,529*
This sample price: priced within the past 7 days for arrival on 8/29/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
Overview
Itinerary
Hotels
Tours
Map
Country Info
Feedbacks
Click for larger image or other views
See all the images
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.
Visit Italy`s scenic capital cityand three of the stunning cities with a Rental Car!. Begin in Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food). From there, pick up the Rental Car and drive along beautiful landscapes en route to Northern Umbria (green 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).
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 Live phone and chat support
This 10 night sample itinerary includes:
Flight into Rome and out of Bologna
Hotel for 3 nights in Rome
Rental Car for 7 days
Hotel 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.
Rome (399)Bologna (11)San Marino City (6)Northern Umbria (2)
Trip Summary
3 nights in 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!
3 nights in Northern Umbria
Northern Umbria is an exquisite unblemished landscape of olive groves, sunflower fields, and wild flowers glowing under the warmth of the Umbrian sunshine. Perugia, the capital, offers 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. To the south, along the Tiber River valley, are the towns of Deruta and Torgiano, best known for their hand-painted ceramics and wine.
Visit and explore the amazing Perugia, Assisi, Gubbio and so much more.
2 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.
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.
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.
Rome - Northern Umbria - San Marino and Bologna (Self Drive)
Photos
Map
Close [x]
This field is required.
Must be a valid username.
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 is an exquisite unblemished landscape of olive groves, sunflower fields, and wild flowers glowing under the warmth of the Umbrian sunshine. Perugia, the capital, offers 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. To the south, along the Tiber River valley, are the towns of Deruta and Torgiano, best known for their hand-painted ceramics and wine.
Visit and explore the amazing Perugia, Assisi, Gubbio 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.
