The Best Islands for Retirement in the World

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Senior couple on the beach
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Editor’s Note: This story originally appeared on Live and Invest Overseas.

The lure of island life is hard to resist.

Be it Treasure Island, Fantasy Island, or Gilligan’s Island, for generations of North Americans, images of near-deserted, sun-soaked shores and the promise of overseas adventure left an indelible impression.

But not all islands are created equal … especially for folks considering making the dream of living on a palm-fringed outpost a reality.

Finding Your Perfect Island Escape

Retired couple laughing and smiling on the beach
wavebreakmedia /

There are many factors to consider when the islands are outside the U.S. such as visas, health care, infrastructure, cost of living, expat community, and more.

Which is exactly what my team here at Live And Invest Overseas and I do each year when we produce our annual Overseas Retirement Index.

This year we’ve identified 10 expat havens, which our findings show offer the best opportunities for North Americans considering a move outside home borders this 2024 — and two of them are islands.

So, if you’re looking to escape the 9-to-5 grind and cast away to a picture-perfect island escape but still enjoy the conveniences and comforts of the modern world, here are my top two recommendations for 2024.

Crete, Greece

The city of Heraklion on the island of Crete, Greece
brittany nathoo /

As the birthplace of the Greek god Zeus, home of Europe’s first advanced civilization, the Minoans, and the crossroads of the three continents of the Old World (Africa, Europe, and Asia Minor), Crete is steeped in rich history and culture.

It’s also a dream destination for sun-seekers, offering the most sunshine hours per year in all of Greece, and for outdoor enthusiasts, with miles of sandy beaches, snow-capped mountains, and untouched wilderness to explore.

Here, a retired couple can enjoy a comfortable life on a modest budget. An average monthly budget of $1,865 is a good guide.

You won’t be short of company should you choose to seek it out. The island is home to around 18,000 expats — including a large contingent of Americans stationed at the Souda Bay naval base — and the locals are a welcoming bunch.

Though the official language is Greek, you can get by in English as just about everyone, from real estate agents to market stall holders, has some level of English.

The health care meets a good standard, the crime rate is low, and the Mediterranean climate means hot summers and gentle winters with no snow-shoveling to worry about.

A Laidback Lifestyle

Charming streets of old town in Rethymno, Crete island, Greece
leoks /

There’s also plenty of year-round entertainment options to stave off island fever, including museums, galleries, shopping, architecture, historical attractions, restaurants and cafes, and cultural events.

Add to that, on Crete the infrastructure is solid, the lifestyle is laidback, and you’re never far from glistening blue waters.

To qualify for Greece’s Financially Independent Person Permit, you need to show that you receive 2,000 euros per month in income. This residency permit is available for two years and is renewable.

Greece also offers a golden visa program, Europe’s most popular, as well as a digital nomad visa.

If you’re looking for a Mediterranean island escape, I suggest you put Crete at the top of your list.

For those happy to travel farther from home shores, consider my No. 1 choice in Southeast Asia.

Phuket, Thailand

Han Kata beach on the island of Phuket, Thailand
nodff /

Ringed by pearly white sands, hemmed in by limestone cliffs, and lapped by the warm waters of the Andaman Sea, Thailand’s biggest island, Phuket, is blessed with undeniable natural beauty, but its charms don’t end there.

The tropical monsoon climate means you’ll enjoy warm weather year-round.

English is widely-spoken, there’s a large expat community of over 100,000, good infrastructure, and a wide range of entertainment options.

It’s an easy place to make new friends, too.

Social groups organize around diverse interests from sports leagues to volunteer opportunities, get-togethers at bars, trivia nights, charity fundraisers, networking events, and more.

Excellent Standards of Living on a Budget

Surfer riding a Fliteboard motorized surfboard
Phuketian.S /

Health care on Phuket is excellent, with a range of public and private facilities, many with English-speaking staff.

Medical fees vary, but you can expect to pay about $30 for a regular visit at a private hospital or $10 for the same visit at a public hospital.

Thailand’s retirement visa is called the Non-Immigrant O-A Visa and its basic requirement is that you are at least 50 years old and receive an income of about $2,000 per month.

This visa is valid for one year at a time, and can be renewed indefinitely.

Overall, Phuket offers the opportunity to enjoy an enhanced standard of living on the same monthly budget (indeed, possibly much less) than the average expat had back in the States or Canada.

A monthly budget of $1,702 will let a retired couple living comfortably here.

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