The Top 20 Islands to Live on in the Caribbean

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We all dream of living in the Caribbean. We all think about waking up to the ocean, being in touch with the natural environment, of connecting with the region’s vibrant culture.

Everybody dreams of doing it — but some actually do it. And they all do it for different reasons.

But there are different kinds of islands for different kinds of desires. Maybe you’re looking for the natural life, away from the hustle and bustle, in harmony with the environment. Maybe you’re looking to take your tech startup to the next level in a friendly environment. Maybe you want to retire as a sailor.

Every island has its own unique identity, and there’s an island waiting for you, whether you want to buy a second home and live there six months out of the year; buy a passport and make it your permanent home; or retire there. You can find the right place for you the Caribbean.

Here are our picks for the top islands to live on in the region — a list we compiled by looking at a range of factors, from the natural environment to the business environment; real estate options to expat communities; culinary offerings to the cultural scene; retirement options to tax climates. We’ve also offered some initial ideas about how to actually go about doing it — and the growing number of citizenship by investment options in the region that range from one-time contributions to national development funds to buying a home on the island.

These are our favorites — and, crucially — they’re starting points. They’re meant to inspire you, to make you think about actually acting upon the dream.

Because once you make the decision that you want to spend more in the Caribbean, you’ll find the right destination.

islands to live on

Grand Cayman It’s the most livable island in the Caribbean, from fast Internet to a broad array of real estate options to culture, food and a growing arts scene. And did we mention Seven Mile Beach? Even better, the new Cayman Enterprise City program is the Caribbean’s best way to move your business to the Caribbean, one focused on startups, with everything from tax mitigation to permanent residency.

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