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.

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.

US Virgin Islands When you’re here, you’re in the United States, meaning U.S. citizens can just make the journey like they were moving to Tuscon. But there is so much here to offer, from the funky, bohemian paradise that is St John to the increasingly hip, urbane St Croix. There’s nowhere that is as procedurally easy to move to in the Caribbean — and the opportunities are abundant, particularly as the islands make their recovery from last year’s storms.

Aruba You’re outside the hurricane belt, overflowing with sunshine and some of the most beautiful beaches in the Caribbean. But Aruba is also a modern, energized place with great shopping, an increasingly robust arts scene and even a budding tech startup sector. It’s a bit like California in the Caribbean, with a Dutch twist.

Antigua and Barbuda There are 365 beaches here, along with a thriving hotel sector and, most importantly, a citizenship by investment program that can start as low as a $100,000 contribution to the country’s National Development Fund. That means moving to one of the Caribbean’s great sandy paradises is well within reach, whether you’re a sailor who wants to take advantage of one of the region’s top yachting destinations or looking for a place to spend several months a year — or looking to buy a ticket and never come back.  

St Barth It doesn’t get any more expensive in the Caribbean, but you might also argue that it doesn’t get any nicer. This tiny jewel has no income tax, nonexistent crime and all of the things you love about France in a tiny Caribbean package. This is the place for a luxe vacation home or a rarefied retirement — although becoming a permanent resident can take some time.

St Kitts While St Kitts has seen a wave of new development in recent years (including the renowned Park Hyatt St Kitts), the island still has a remarkably untouched landscape, offering a tranquil, old-school Caribbean ambience that is hard to find these days when you’re thinking about a new place to move. And the island also has one of the oldest citizenship by investment programs, one that’s particularly effective if you’re looking to buy property in one of the island’s growing portfolio of projects.

British Virgin Islands Looking to move to a boat in the Caribbean? The Caribbean’s greatest sailing destination is the place, whether you want to buy a boat and live on it, spend your summers chartering away or just find a tucked-away hillside villa to spend your retirement in.

Barbados Genteel and charming, Barbados is elegantly laid-back, with a growing business community, excellent broadband infrastructure and a wonderful number of restaurants. The real estate is pricey, but you get what you pay for, and the expat community, mostly made up of UK nationals, is strong.

Providenciales, Turks and Caicos Looking for a condo right on one of the Caribbean’s greatest beaches? This is your bet, with a truly remarkable offering of units in oceanfront buildings on Grace Bay Beach. There’s a budding expat community here, one of the region’s great culinary scenes and a totally relaxed vibe that makes it a great place for a split-year retirement.

Bonaire It’s low-key, it’s casual and it’s sparklingly beautiful. This island in the Dutch Caribbean has long been a haven for divers and snorkelers, and its under-the-radar status means it boasts some of the best value waterfront real estate in the Caribbean. Its position in the Netherlands meaning you can find high-level healthcare, too, making it a particularly good retirement destination.

Curacao This is not a place for slowing down. Another of the most livable places in the region, this Dutch Caribbean hotspot marries urban charm and energy with jaw-droppingly beautiful beaches and European levels of development. That’s along with a thriving business scene and an increasing number of nonstop flights.

Harbour Island It may be minuscule, but this historic outpost in the Out Islands of The Bahamas will immediately make you fall in love. And after just a short time here, you’ll see why so many others have fallen in love, too. There’s just a lovable, friendly community here, one that celebrates its history but also is extremely open-minded. While the real estate is pricey, you’ll find some of the region’s most extraordinary historic architecture.

Saint Lucia Looking for rainforests and cacao plantations, untouched beaches and vibrant Creole culture? What if you could find all that and still live somewhere with a cosmopolitan energy? Saint Lucia has it all, and, even better, it offers citizenship by investment, meaning for a contribution to the island’s National Economic Fund of as low as $100,000 you can apply be approved for citizenship.

Dominica Looking to move to the most naturally beautiful place in the entire Caribbean? This is for you, with stunning volcanoes, waterfalls and an emphasis on eco-friendly, authentic living. It’s a place that has produced an almost absurd number of centenarians — and when you start to get into the lifestyle here you’ll see why. Even better? Dominica has a CIP program as well, starting as low as a $100k contribution to the island’s Economic Diversification Fund.

Martinique This French Caribbean island will make you feel like you’re actually in France — except with spectacular beaches, the world’s best rum and lush rainforests. It’s just about the most developed island in the Caribbean, from roads that are as good as the ones you find in mainland France to sprawling supermarkets and perhaps the region’s most underrated culinary scene. This is like moving to Europe — but it’s just three hours from mainland America and has all of the things you love about the Caribbean.

Grenada The same things that make Grenada one of the Eastern Caribbean’s hottest tourism destinations make it an attractive place to live,  from a host of undiscovered beaches to the added energy of having a large medical student population. It’s also got a wave of luxury hotels in the pipeline that include a residential component, making it a great spot for a second home or a luxury retirement. And yes, there’s citizenship by investment here, too, from a $200,000 contribution to the island’s NTF or an approved real estate investment.

Nevis While St Kitts has a bit more energy and bustle, Nevis is a tiny little untouched jewel, far from the global madness, a small island with friendly people and beautiful scenery. It’s one of the region’s best retirement destinations for precisely that reason – and as part of the twin-island federation you can acquire citizenship here, even by fractional ownership in projects like the Four Seasons Villas.

Treasure Cay You may not know it, but the Treasure Cay community in Abaco is the largest residential development in the entire Caribbean — from marinafront homes to beachfront villas. And it’s a self-contained destination, with a true town-like atmosphere. And if you have a boat, it’s just about heaven, with the many maritime destinations of the Abacos just a short ride away. That all adds up to the perfect vacation home destination — or a truly great place to spend your retirement years.

Nassau It’s amazing just how much Nassau has transformed in recent years. The island that’s just a 35-minute plane ride from Miami has become one of the most sophisticated, cosmopolitan places in the Caribbean, with a vibrant culinary scene, a robust business sector, booming real estate development and a thriving expat community. And its proximity to Florida makes it perfect for just about any kind of move.

Ambergris Caye, Belize Is there are more popular destination for expats in the whole Caribbean? Ambergris Caye has changed a lot in recent years, but it still has the funky, beach-lovers’ charm that brought everyone there in the first place. And while prices have gone up, the value for beachfront and waterfront property is still as good as you’ll find in the Caribbean.

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