Interested in our Partner Program for businesses or our Local Guide Program for experienced expats and digital nomads? Click here to learn more.
Expat Exchange - Best Places to See While on a Look-See Trip to Italy (Plus, Itineraries) 2024
Expat Exchange
Free MembershipSign In
Via Garibaldi in Turin, Italy

Best Places to See While on a Look-See Trip to Italy (Plus, Itineraries)

By Joshua Wood, LPC


Summary: For those contemplating a move to Italy without a specific locale in mind, embarking on a look-see or exploratory journey to explore various expat havens can provide invaluable insights. Here are some top suggestions for places to explore while scouting out Italy.

Embarking on a Look-See trip to Italy is an invaluable step for anyone considering a move to this culturally rich country. Such a trip allows potential expats to explore various cities and towns, get a feel for the local lifestyle, and assess practical matters like housing, healthcare, and transportation. It's an opportunity to envision daily life beyond the allure of vacation hotspots, ensuring that the decision to move is well-informed and aligns with personal and professional needs.

Recommended Itineraries

For a 10-day trip, consider a route that covers diverse regions, starting with the bustling metropolis of Milan, then heading to the historical charm of Florence in Tuscany, followed by the serene countryside of Umbria with stops in Perugia and Assisi. Conclude with the eternal allure of Rome. A 20-day trip allows for a more extensive exploration, including the aforementioned cities, along with the coastal beauty of Naples and the Amalfi Coast, the unique trulli houses of Alberobello in Puglia, and the vibrant island life of Sicily, with visits to Palermo and Catania.


Milan, Italy's financial hub, is a magnet for expats and digital nomads seeking a dynamic urban environment. With a population of over 1.3 million, it offers a blend of modern amenities and historical sites. The cost of living is on the higher side, but the city compensates with excellent public transport, a thriving job market, and a rich cultural scene. Milan is also well-positioned for travel, with the Alps and the Mediterranean coast within easy reach.

Travel Tip: Don't miss the chance to see Leonardo da Vinci's "The Last Supper" at the Convent of Santa Maria delle Grazie. For a culinary treat, visit the historical Luini Panzerotti for a taste of their famous panzerotti.


Florence, the cradle of the Renaissance, is a favorite among expats who appreciate art, history, and a slower pace of life. The city's population hovers around 380,000, offering a small-town feel with the conveniences of a city. Expats enjoy a lower cost of living compared to Milan, while still having access to Florence's rich tapestry of museums, restaurants, and artisan shops. The Tuscan countryside, with its vineyards and olive groves, is just a short drive away.

Travel Tip: Experience the panoramic views of Florence from Piazzale Michelangelo, and indulge in the culinary delights at Trattoria Mario, a local favorite for authentic Tuscan cuisine.

Umbria (Perugia and Assisi)

Umbria, known as the "Green Heart of Italy," is ideal for those seeking a tranquil lifestyle amidst rolling hills and medieval towns. Perugia, the regional capital, offers a vibrant student life and a lower cost of living, while Assisi is a serene sanctuary famous for its religious heritage. Both towns provide a sense of community and connection to Italian culture and history.

Travel Tip: In Perugia, visit the National Gallery of Umbria for a dose of art, and enjoy a chocolate treat at the renowned Perugina Chocolate House. In Assisi, the Basilica of Saint Francis is a must-see for its frescoes and spiritual significance.


Rome, the Eternal City, is a living museum with a population of over 2.8 million. It's a city where ancient history and modern life coexist. Expats and digital nomads are drawn to Rome for its vibrant street life, culinary delights, and endless cultural experiences. The cost of living can vary greatly, but the city offers neighborhoods to suit a range of budgets and lifestyles. Rome's international airports and train systems also make it a convenient hub for travel within Italy and beyond.

Travel Tip: Take a stroll in the Trastevere neighborhood for its charming streets and lively atmosphere. For a unique dining experience, visit Da Enzo al 29, known for its traditional Roman dishes.

Naples and the Amalfi Coast

Naples offers a gritty yet authentic Italian experience, with a lower cost of living than Rome or Milan. It's a city of contrasts, with a rich history and a reputation for the best pizza in Italy. The nearby Amalfi Coast provides breathtaking coastal views and a slower pace of life in towns like Positano and Amalfi. This region is perfect for those seeking a balance between urban energy and seaside tranquility.

Travel Tip: Visit the archaeological sites of Pompeii and Herculaneum to step back in time, and enjoy a pizza at Sorbillo, one of Naples' most famous pizzerias.

Puglia (Alberobello)

Puglia, the heel of Italy's boot, is an up-and-coming region for expats, known for its whitewashed hill towns, centuries-old farmland, and lengthy Mediterranean coastline. Alberobello is renowned for its trulli, traditional dry stone huts with conical roofs. The cost of living in Puglia is relatively low, and the region offers a laid-back lifestyle with a strong sense of local culture and community.

Travel Tip: Explore the Trulli of Alberobello, a UNESCO World Heritage site, and savor the flavors of the region at Ristorante La Cantina, famous for its local cuisine.

Sicily (Palermo and Catania)

Sicily, the largest island in the Mediterranean, is a cultural melting pot with a diverse history reflected in its architecture, cuisine, and traditions. Palermo, the capital, is known for its bustling markets and vibrant street life, while Catania offers a baroque cityscape with Mount Etna as a dramatic backdrop. The cost of living is among the lowest in Italy, making Sicily an attractive option for retirees and digital nomads alike.

Travel Tip: Visit the Palermo Cathedral and the Palatine Chapel for a glimpse of the city's architectural splendor. In Catania, the fish market, La Pescheria, offers a lively and authentic Sicilian experience.

About the Author

Joshua Wood Joshua Wood, LPC joined Expat Exchange in 2000 and serves as one of its Co-Presidents. He is also one of the Founders of Digital Nomad Exchange. Prior to Expat Exchange, Joshua worked for NBC Cable (MSNBC and CNBC Primetime). Joshua has a BA from Syracuse and a Master's in Clinical and Counseling Psychology from Fairleigh Dickinson University. Mr. Wood is also a licensed counselor and psychotherapist.

Some of Joshua's articles include Pros and Cons of Living in Portugal, 10 Best Places to Live in Ireland and Pros and Cons of Living in Uruguay. Connect with Joshua on LinkedIn.



Via Garibaldi in Turin, Italy


Top-quality coverage for people who live, work, study and travel internationally.
Get Quote


Top-quality coverage for people who live, work, study and travel internationally.
Get Quote

Contribute to Italy Network Contribute
Help others in Italy by answering questions about the challenges and adventures of living in Italy.


Copyright 1997-2024 Burlingame Interactive, Inc.

Privacy Policy Legal Partners & Local Guides