An Expat’s Guide to Discovering Italy’s Most Unexpected Experiences

I’m often asked the same question, whether by tourists engaging in casual conversation at the bar over a morning macchiato, inquisitive strangers who stop to pet my dog, or eager study abroad students curious to learn about the post-college option they didn't know existed, “What brought you to Italy?” I never really know how to answer because I’m always inclined to respond to a question I find much more revealing, “Why did I stay?”

Few things are more intimidating than boarding a one-way flight to another country devoid of a single friend or a single word of Italian. From the moment I first stepped foot in Florence as an eager study abroad student, I dreamed of calling the romantic city my home. When my craving for adventure was at its most restless, I made the decision to move, “for just one year.” But like pizza or pasta, it’s seemingly impossible to stop at just one taste of Italy, and I’m now going on year five of living in Florence with my husband and our adopted dog, Sonny. 

It’s an unwritten rule that when you’re an ex-pat in Italy, you must take advantage of the country’s convenient network of transportation. After spending a few hours on any given train, you’re guaranteed to end up in one of the world’s most breathtaking, historic, and celebrated cities. Although no list is ever long enough to encompass the places I’ve discovered throughout my travels, the following cities host some of Italy’s most unexpected and lesser-known experiences, and are some of my favorite ways to start, end, or be the center of any trip:

Genoa

As far as Mediterranean cities go, Genoa is in a league of its own. This northern maritime capital is a treat for the senses, from its adornment with vibrant architecture to the sea salt that wafts down each tapered alleyway. The heart of the port city is undoubtedly Porto Antico, the old port, where famous Italian architect Renzo Piano made it his mission to create a space where culture, leisure, and imagination meet. The largest square on the Mediterranean is home to newer attractions like the Aquarium of Genoa, the Bigo, a panoramic lift that offers a unique perspective of the city, and the Biosphere, a glass and steel greenhouse that both displays and defends the preservation of tropical forests.

Milan

Milan is undoubtedly amongst the world’s most metropolitan cities and is known as Italy’s primary hub of hustle and bustle. But its fashion and finance scene often overshadow its deep-rooted and dynamic contemporary art scene. The Fondazione Prada, a breathtaking one-stop-shop for cultural immersion, is one of the most underrated but incomparable must-sees in Milan. The Fondazione hosts both permanent and rotating exhibitions across literature, cinema, music, and science by artists like Carla Accardi and Jeff Koons.

Not only is the Fondazione itself a work of art, (the adjacent towers, one appearing to be solid gold, can’t be missed), but so is the venue’s surroundings. The nearby Piazza Olivetti, named after the enlightened Italian entrepreneur, is a masterpiece of urban regeneration that’s driven by Milan’s goals for a more sustainable future.

Venice

It’s impossible to talk about contemporary art in Italy without referencing La Biennale, the global event at the forefront of contemporary art trends. In addition to being the home to landmarks like Piazza San Marco and iconic canals, “The Floating City” has been the center for the world’s modern artists to reveal their works for over 120 years. Make sure your gondola stops to let you off at the International Gallery of Modern Art in Ca’ Pesaro, where an enriched collection will transport you through pieces that marked the 20th century.

Bologna

Italy’s most popular university town is unsurprisingly also its most avant-garde. Take the Opificio Golinelli, for example, the open ecosystem industrial space inaugurated in 2015 can be considered its own city within Bologna. The education, research, and training center houses laboratories, classrooms, offices, spaces for exhibitions and workshops, and is on track to become one of the most important centers of reference for innovation in Europe.

Florence

A UNESCO World Heritage Site in and of itself, Tuscany’s capital boasts renowned galleries like the Uffizi and Accademia. Lesser known but just as beautiful are exhibitions and installations in historic locations such as Forte del Belvedere and the Boboli Gardens, where the panoramic views are just as breathtaking as the architecture. Grandiose palaces like Palazzo Strozzi are home to rotating exhibitions so beautiful and interesting that locals are in attendance on a regular basis. Florence is also the home to centers dedicated to the arts, like the new Innocenti museum, which includes architectural masterpieces, and Cinema La Compagnia, devoted to the art of filmmaking.

After checking those off, venture to the Tuscan hillsides where you’ll find the most beautiful hidden gems. A short car or train ride in any direction will land you in a number of Tuscany’s charming towns, where the perfect combination of rolling green hills, cobblestone streets, and rich history make for an incomparable day or weekend escape from Florence’s city center.

Rome

Rome is considered by many to be an “open-air museum” that requires no ticket for admission. Wander through the centro storico (historic center) to view freestanding works of art and architectural achievements such as the Pantheon and Piazza Navona. If you’re yearning to view works of art by the great masters Caravaggio, Bernini, Canova, and more, book your ticket in advance for the Galleria Borghese after a stroll through the vast public park.

But even though you’re coming for the Colosseum, stay for the more modern architectural achievements like the MAXXI. The prize-winning building designed by renowned architect Zaha Hadid houses two museums in one, with a section fully dedicated to art and another to architecture. The MAXXI is considered to be less of a museum and more of a hub for creativity, offering a rich, multidisciplinary program highlighting both Italian and global exhibitions that reflect modern issues like sustainability, political demonstration, and urban planning.

Matera

Despite the 2019 European Capital of Culture being made up of Sassi (which literally means ‘stones’), one of the most ancient cities in the world has managed to seamlessly integrate innovation. Once a heartbreaking symbol of poverty, the unique Sassi are the reason Matera is a UNESCO World Heritage Site, and progressive architects have converted the stone caves into romantic hotels, unique restaurants, and enchanting museums like The Museum of Contemporary Sculpture (the only cave-museum in the world). Further proving the magic of Matera is ever-present, along the streets of the city you’ll find temporary installations and frescos that represent Matera’s evolved essence.

Palermo

A quick flight or ferry will land you in Sicily, the autonomous Italian island that has a culture of its own and a deep-rooted history of migration. In the face of the relevant European migration crisis, Palermo, Sicily’s capital, is working to reinvigorate traditions of openness and hospitality through exhibitions at Palazzo Butera. The palace overlooking the city’s waterfront, once owned by the princes of Butera, is a newly established center that uses art to illustrate the ties that lie beneath apparent cultural differences, exemplify the power of diversity, and inspire solutions for social development.

Whether you visit the north or the south, come for just one city or stay forever, Italy is a traveler’s dream because there’s always more to see. Though characterized by its deep history and ancient landmarks, Italy has managed to transition to the modern age while maintaining its unique and irresistible style. After almost 250 weekends spent exploring the country from top to bottom (not to mention countless hours spent in train-station Feltrinelli bookstores devouring guides and plotting all my future trips), I’m positive I’ll never be immune to the unparalleled magic and charm this country holds.