Choosing Between Rome, Milan and Florence: The Best Italian Cities for Expat Families

Italy is one of the most desirable countries in the world for high-net-worth individuals (HNWIs) and international families seeking a refined lifestyle, rich culture, and attractive tax incentives. But once the decision to move is made, the real challenge begins: where in Italy should you relocate your family?

While many smaller towns offer charm and tranquility, three cities stand out for expats with families who want access to world-class education, international connectivity, high-quality real estate, and professional services: Rome, Milan, and Florence.

Each city offers a different mix of opportunities and challenges. In this guide, we help you compare them across key criteria to make the best relocation decision for your family and your wealth.

Rome: History, Prestige, and International Presence

Rome is Italy’s political and historical capital, and one of the most iconic cities in the world. For HNWI families, Rome offers an exceptional blend of international schools, private healthcare, and access to diplomatic networks. Many embassies and international organizations are based here, making it ideal for globally mobile families who value connections and cultural depth.

The real estate market in Rome is mature and stable. Prestigious neighborhoods such as Parioli, Prati, and Aventino offer elegant villas and luxury apartments with access to international schools and green spaces. Prices per square meter are still competitive compared to major global capitals.

In terms of education, families can choose from several international schools, including the American Overseas School of Rome (AOSR), the British School, and the French Lycée Chateaubriand. These institutions are well-established and offer full K-12 programs in English or other languages, including IB curricula.

Rome is best suited for those seeking stability, prestige, and tradition. However, bureaucracy can be slower, and the pace of life less efficient than in Northern Italy.

Milan: Italy’s Financial Engine and Global Business Hub

Milan is the economic capital of Italy and home to the country’s largest concentration of private banks, family offices, and asset managers. It is a natural fit for HNWI expats who want to continue operating internationally while benefiting from Italy’s flat tax regime, now set at €200,000 per year for new residents.

The city combines modern infrastructure, a strong expat community, and efficient public services with a global business mindset. Milan’s international schools are among the best in Europe, including the International School of Milan, American School of Milan, and the Deutsche Schule Mailand. Many of these offer IB and multilingual tracks.

Real estate in Milan is more expensive than in Rome or Florence, especially in zones like Brera, CityLife, and Porta Venezia. However, the liquidity and quality of the market are unmatched in Italy, and the rental yield is also higher thanks to strong demand.

Milan also shines in terms of international mobility, with three airports (Linate, Malpensa, Bergamo) and high-speed rail connections to Switzerland, France, and the rest of Italy.

Families who relocate to Milan often do so not only for lifestyle, but also for business development, networking, and strategic positioning in the EU market.

Florence: Culture, Comfort, and Slower Luxury

Florence offers a very different experience—more intimate, artistic, and balanced. The city is smaller and less intense than Rome or Milan, but extremely attractive to families who prioritize lifestyle over business. It combines Renaissance beauty with modern services, and is surrounded by Tuscany’s most prestigious real estate.

Expat families are drawn to Florence for its safety, international atmosphere, and strong artistic heritage. While the international school options are fewer than in Rome or Milan, they are high quality, including the International School of Florence, one of the oldest in Europe.

Real estate in Florence offers historic palazzi, villas on the hills, and countryside estates within 30 minutes of the city. For families who want to integrate privacy, comfort, and proximity to a major cultural hub, Florence is ideal.

However, Florence may not be the best option for those who require frequent business travel, access to major corporate services, or fast-paced professional environments. It’s more suited for those seeking a secondary residence, retirement relocation, or a family base with a focus on wellbeing and education.

Education, Healthcare, and Family Services

All three cities provide access to high-level international education, but Milan leads in terms of variety, followed by Rome, with Florence offering more limited—but excellent—options.

Healthcare is top-tier in private institutions across the country. Rome and Milan have the largest number of internationally accredited clinics, while Florence provides outstanding care, albeit with fewer choices.

Family services such as private childcare, tutoring, language support, and sports academies are widely available in all three cities, but Milan again leads in international breadth and availability.

Tax Planning and Flat Tax Access

One of the most powerful reasons for relocating to Italy as an HNWI is the flat tax regime, which allows you to pay a fixed annual tax of €200,000 on foreign income, regardless of amount. All three cities provide access to professionals who can help structure your move to fully benefit from this regime.

Additionally, families with multiple members can take advantage of reduced flat tax options (€100,000 for relatives), trust planning, and real estate structuring to optimize succession, residence, and income flows.

Knotted works with families in Milan, Rome, and Florence to set up integrated relocation strategies, combining immigration, tax, real estate, and lifestyle planning.

Conclusion: Which City Wins?

There is no single “best” city—it depends on your priorities.

Choose Milan if you want proximity to financial markets, a cosmopolitan lifestyle, and quick access to global networks. It is the best city in Italy for entrepreneurs, executives, and internationally active families.

Choose Rome if you value history, diplomacy, tradition, and a sense of grandeur. It's ideal for families looking to connect with international institutions or relocate with the support of a strong global community.

Choose Florence if you want peace, elegance, and cultural immersion for your family, without sacrificing access to international services.

Wherever you go, Italy offers a sophisticated platform for HNWIs to build a life that combines beauty, structure, and opportunity.

Ready to choose your city and plan your move?Write to us at info@knotted.ch or message us directly on WhatsApp at +41 76 771 30 22 to start your family’s relocation journey with Knotted.