If you’re asking yourself where to live in Portugal as an American, you’re not alone. More U.S. citizens are discovering that Portugal offers a perfect blend of affordability, safety, high-quality healthcare, and a welcoming lifestyle, especially in Madeira Island. Whether you’re retiring, working remotely, or simply craving a sunnier way of life, this guide outlines the top 7 places in Portugal that American expats consistently rate as the most livable.
1. Funchal, Madeira
As the capital of Madeira Island, Funchal blends natural beauty with modern conveniences. Americans appreciate the walkable city centre, international schools, access to healthcare, and the friendliness of locals. The mild subtropical climate makes year-round outdoor living a reality, and its tax incentives for foreign residents are a key attraction.
Funchal is also the economic and cultural heart of the island, hosting international digital nomads, retirees, and entrepreneurs. With direct flights from mainland Europe and a robust fibre internet network, it’s increasingly popular among remote workers.
Families will be happy to know that Funchal ranks chiefly as the best overall city to raise children.
2. Calheta, Madeira
For those wondering where to live in Portugal as an American who wants more space and tranquillity, Calheta offers golden beaches, newly built villas, and a slower pace of life. It’s ideal for families or retirees looking for a secure, sunny town with ample hiking, sailing, and whale watching opportunities.
Calheta has seen a rise in expat-owned eco-retreats and boutique hotels, reflecting its popularity among Americans seeking a balance between nature and quality of life.
3. Ponta do Sol, Madeira
Ponta do Sol is Madeira’s sunniest village, a charming coastal town that has become a hub for the digital nomad community. The municipality even runs a dedicated coworking program that welcomes remote workers worldwide.
The peaceful atmosphere, sea-view properties, and local cafés create an ideal lifestyle for Americans escaping big-city stress. Its small scale makes integration easy, with plenty of community-driven events and English-speaking locals.
4. Santa Cruz, Madeira
Just minutes from the international airport and within easy reach of Funchal, Santa Cruz is ideal for Americans who want the conveniences of urban life without the hustle. It offers affordable real estate, easy transportation, and excellent public services, making it especially attractive to families and seasonal residents. Its proximity to Madeira’s tech and business hubs also supports professionals relocating for work or starting ventures within the Madeira International Business Centre.
5. Lisbon
As the capital city, Lisbon remains a top destination for Americans. It offers the most comprehensive infrastructure, top universities, and a cosmopolitan vibe. The city has a growing American expat community, with expat-run businesses, cultural institutions, and support networks.Lisbon is ideal for those who want urban energy, international cuisine, and a thriving tech and startup scene. However, it’s important to note that the cost of living is higher than in Madrid or smaller inland cities.
6. Cascais
Located just 30 minutes from Lisbon, Cascais is a refined coastal town known for its marina, golf courses, and scenic beaches. It’s one of the safest areas in Portugal and is home to many embassies, international schools, and luxury residences.
Cascais suits American expats who prioritise prestige, privacy, and lifestyle. It’s an excellent place to raise children, enjoy seaside living, and network with international professionals.
7. Coimbra
For Americans looking for affordable living with an intellectual twist, Coimbra, Portugal’s university city, stands out. The cost of living is notably lower than in Lisbon or Cascais, while cultural richness and educational resources are abundant. It attracts young professionals and retirees who enjoy history, music, and literature. The pace is relaxed, and English is widely spoken due to the international student population.
Final Thoughts: Why Madeira Deserves Special Attention
If you’re still wondering where to live in Portugal as an American, Madeira Island presents a compelling case. It combines many of the country’s most desirable traits, such as safety, nature, lower living costs, and tax efficiency, with an open-door attitude toward foreigners. Madeira’s mix of charm and opportunity is hard to beat, whether you’re a remote worker, investor, or retiree. For those ready to take Madeira’s next step, Madeira Corporate Services can assist with relocation planning, tax structuring, real estate due diligence, and immigration processes.

The founding of Madeira Corporate Services dates back to 1996. MCS started as a corporate service provider in the Madeira International Business Center and rapidly became a leading management company… Read more