One route is through the Golden Visa program. In exchange for foreign investment, Golden Visa holders are granted a residence permit. After holding a Golden Visa for five years, you can apply for permanent residency.
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Of course it is possible to live in Madeira full time, but there are entry requirements, as documented here. There are around 1000 expat Brits on the Island full time. I would suggest joining one of the expat blogs for further info. Well, you certainly cannot simply Leave and re-enter every 6 months!
Funchal, the capital of Madeira Island, is known for its beautiful landscapes, mild climate, and relaxed lifestyle. According to Numbeo, a family of four can expect to spend around 1,943.8€ per month without rent in Funchal, while a single person's estimated monthly costs amount to 542.5€ without rent.
Buying property in Portugal allows you to acquire a Portugal residence permit, as long as you stay in the country for a minimum of 14 days each two years. That means you can buy a property in Portugal and get residency. Moreover, you may apply for citizenship and an EU passport five years after obtaining residency.
UK nationals can still visit without a visa, but can only stay for up to 90 days within 180 days. If you'd like to visit for longer than this, then you will need to apply for a visa.
Popular areas for expats include Funchal, the capital city, as well as Ponta do Sol, Calheta, Santana, São Martinho, and Ribeira Brava. These areas offer a mix of coastal and mountain living options.
If your definition of quality of life means safety, tranquillity, natural beauty and little traffic, then Madeira could be a good option. Far from the bustle of Lisbon and Porto, the island is calm and peaceful.
Choosing to buy or rent a property in Madeira Island and moving for retirement, is absolutely the best choice. In Madeira you can enjoy not only one of the best climates in the world and almost the most hours of sunshine in Europe, but also good health services and favorable tax climate for retirees.
This is also the place where most expats and digital nomads live so people are more likely to speak English. With over 100,000 people living in Funchal, it is the main center of Madeira. The capital is known for its lively nightlife, incredible restaurants, and for having loads of cultural activities to enjoy.
The average standard of living tends to be a bit lower than in mainland Portugal, and the local autonomous government gives generous subsidies coming from the tourist industry revenues and from the Portuguese national budget. Go where the locals go and everything will be cheap.
The island of Madeira is also attracting keen interest, with 1,342 Britons living there in 2020. That number is expected to increase from 2022, since, despite its popularity as a tourist destination, property there will still qualify for inclusion in Portugal's Golden Visa scheme.