Best Places to See While on a Look-See Trip to Italy (Plus, Itineraries)
Summary: Considering a move to Italy but uncertain about where to settle? Venturing on an exploratory trip to visit multiple popular expat destinations can be incredibly enlightening. Here's a list of recommended places to consider during your exploration of Italy.
Embarking on a Look-See Trip is a crucial step when considering a move to Italy. It allows you to immerse yourself in the culture, explore different regions, and get a genuine feel for what life could be like. This firsthand experience is invaluable in helping you make an informed decision about where you might want to live.
Recommended Itineraries
For a 10-day trip, consider starting in the north and working your way south. Begin in Milan, then head to Bologna, Florence, and finally Rome. For a 20-day trip, include more regions and cities such as Turin, the Cinque Terre region, Perugia, and the Amalfi Coast. This will give you a broader perspective on the diverse landscapes and lifestyles Italy offers.
Milan
Milan is Italy's financial hub and a bustling metropolis with a population of around 1.3 million. Known for its fashion industry and vibrant nightlife, it attracts many digital nomads and expats. The is higher than in other Italian cities, but the opportunities and amenities make up for it. Life in Milan is fast-paced and cosmopolitan.
Travel Tip: Visit the iconic Duomo di Milano, a stunning cathedral that is the symbol of the city.
Bologna
Bologna, with approximately 390,000 residents, is known for its rich culinary scene and historic architecture. It offers a high quality of life at a more affordable cost than Milan. Its central location makes it easy to travel to other parts of Italy. Bologna is a great choice for food lovers and those seeking a balance between city life and tranquility.
Travel Tip: Try the famous tortellini at Osteria dell'Orsa, a popular local eatery.
Florence
Florence is the capital of the Tuscany region and has a population of about 380,000. It is renowned for its art, culture, and Renaissance architecture. The cost of living is moderate, and the city offers a mix of urban and rural lifestyles. Florence is ideal for those who appreciate art, history, and scenic landscapes.
Travel Tip: Visit the Uffizi Gallery, one of the most famous art museums in the world.
Rome
Rome, the capital of Italy, is home to around 2.8 million people. It is rich in history, culture, and ancient architecture. The cost of living varies by neighborhood, but it generally offers good value for money. Rome is perfect for those who want to live in a city steeped in history with a vibrant, urban atmosphere.
Travel Tip: Explore the ancient Roman ruins at the Colosseum.
Turin
Turin, with a population of about 880,000, is known for its elegant architecture and sophisticated culture. It offers a high quality of life with a lower cost of living compared to Milan. Located near the Alps, it is perfect for those who enjoy outdoor activities and a refined urban lifestyle.
Travel Tip: Visit the Egyptian Museum, one of the largest of its kind in the world.
Cinque Terre
The Cinque Terre region consists of five coastal villages: Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso al Mare. This area is known for its colorful houses, terraced vineyards, and stunning coastal views. It is ideal for those seeking a slower pace of life in a picturesque setting. The cost of living is moderate.
Travel Tip: Hike the trails connecting the five villages for breathtaking views.
Perugia
Perugia, the capital of the Umbria region, has a population of about 165,000. It is known for its medieval architecture and vibrant student life. The cost of living is affordable, and it offers a high quality of life. Perugia is great for those who want to live in a historic city with a lively atmosphere.
Travel Tip: Visit the Perugia Cathedral, a stunning example of Gothic architecture.
Amalfi Coast
The Amalfi Coast is a scenic stretch of coastline with towns like Positano, Amalfi, and Ravello. It is known for its dramatic cliffs, beautiful beaches, and luxurious resorts. The cost of living is higher, but the area offers an unparalleled quality of life. It is perfect for those seeking a coastal lifestyle with stunning views.
Travel Tip: Drive along the Amalfi Coast Road for breathtaking coastal views.
About the Author
Betsy Burlingame is the Founder and President of Expat Exchange and is one of the Founders of Digital Nomad Exchange. She launched Expat Exchange in 1997 as her Master's thesis project at NYU. Prior to Expat Exchange, Betsy worked at AT&T in International
and Mass Market Marketing. She graduated from Ohio Wesleyan University
with a BA in International Business and German.
Some of Betsy's articles include 12 Best Places to Live in Portugal, 7 Best Places to Live in Panama and 12 Things to Know Before Moving to the Dominican Republic. Betsy loves to travel and spend time with her family. Connect with Betsy on LinkedIn.
Additional Information:
- Italy Guide
- Healthcare & Health Insurance in Italy
- Members Talk about Healthcare & Health Insurance in Italy
- Best Places to Live in Italy
- Real Estate in Italy
- Guide to Real Estate in Italy
- Pros & Cons of Living in Italy
- Cost of Living in Italy
- Healthcare in Italy
- 5 Expat Moms Talk about Having a Baby in Italy
- Tips for Expats in Italy
- Top 6 Cities in Italy for Expat Jobs
- 2026 Guide to Living in Italy
- Pros and Cons of Living in Italy 2026
- 2026 Guide to Moving to Italy
- More Advice about Retiring in Italy


