Packing up and heading out for a Caribbean island. It’s the dream for so many of us. But what if you actually did it? We’re here to help with inspiration. Whether you’re looking for a an island high on quiet, or a developed, metropolitan place, the Caribbean has a bit of everything — no matter if you’re planning to move or simply buy a vacation home for part-time living. Each one of these places is different — each has its own benefits and its own challenges (and its own residency laws and requirements). And there are great islands that aren’t on this list. But these islands rise to the top — they’re the places we think are worth buying a one-way ticket for.
Saint Martin
There’s a reason so many people come to the French side of this island — there’s an energy here that you don’t often find alongside beaches this beautiful. It’s hard to find better food anywhere in the Caribbean, and you also have great airlift, great island hopping availability, European-standard schools and healthcare and a vibrant mix of cultures, languages and experiences.
Grand Cayman
This island has the highest standard of living in the entire region (and a very friendly tax regime), and that comes across everywhere you look. Beyond the diving and the beaches, both of which are spectacular, there’s a significant supply of beachfront condos and homes, top-level restaurants, the new Health City Cayman Islands (a ground-breaking Caribbean healthcare facility) and it’s just an hour away from Miami.
Tortola
This is one of the most beautiful corners of the Caribbean. You look in any direction and there’s a jaw-dropping, green-covered island not too far away. It’s also one of the friendliest places in the region, with superb villas, a solid level of development and a very business friendly climate.
Anguilla
Looks can be deceiving. If you squint, you just see unbelievable, largely empty beaches. If you look closer, you see a remarkably lively island, with more than 100 high-level restaurants, abundant real estate opportunities (from villas to buildable land), easy access from St Martin and that old-fashioned Caribbean tranquility.
Bonaire
Paradise for nature lovers. It’s outside of the Hurricane Belt, it’s got some of the best diving in the Caribbean, it’s got a large airport, and it’s got a young, dynamic energy. It’s also got a small town feel, where you feel safe and part of the community, whether you’re old or just off the plane. And it’s backed by Dutch standards in many respects.
Providenciales
It’s got a nearly unmatched condo product and nearly unmatched beaches. It’s not busy, but it’s never boring, and there’s great airlift with the continental United States just an hour away.
Martinique
There’s a level of infrastructure and development here that’s largely beyond anywhere in the Caribbean: think fresh-paved roads and highways, a walkable, dynamic capital, increasingly strong airlift from the US and everything you’d expect from a department of France: delectable food, rum and a Mediterranean-meets-the-Caribbean vibe.
St John
This tiny corner of the US Virgin Islands is the territory’s best-kept secret — it has the feel of a bohemian artists’ colony. It’s laid back, it’s not built up, 60 percent of the island is a national park, and it’s a short ferry ride from easy-to-fly-to St Thomas.
St Kitts and Nevis
We put this twin-island federation together because it’s hard to separate one from the other — St Kitts is the place to do business, the place to study, while Nevis is an even more laid back, untouched paradise. Both are great options for those seeking small islands with big potential. And it’s got the best Citizenship by Investment programme in the Caribbean.
Guadeloupe
Few travelers know very much about this place, which is a shame: it’s an almost remarkable mix of international-standard development and tropical life — there are five main islands in this archipelago, and each has its own ambiance, its own spirit, its own charm. (Above: the island of Terre de Haut)
Aruba
Spectacular beaches on an island outside of the Hurricane Belt. There’s really good connectivity from the United States, especially the Northeast. It’s a modern, contemporary island that hasn’t forgotten its roots. Aruba is a melting pot of cultures, of continents, of cuisines – and it’s also becoming the greenest island in the Caribbean.
Curacao
This island’s capital is one of the most cosmopolitan places in the region — and there’s a unique Dutch Caribbean feel no matter where you are, whether on the beaches or the bridges. It’s also uniquely positioned to do business with both the United States and South America.
Barbados
It’s a mix of old and new here — terrific education and standard of living are reasons why this frequently tops the list of highest human development in the region. It’s also a refined, comfortable place marked by an overwhelming gentility. It has the benefits of the Old Caribbean, but the drive of a modern country.
Ambergris Caye
This has long been a haven for expatriates, and with good reason: the ratio of standard of living to cost of living here has long been among the highest on the Caribbean Sea. This largest island in Belize is an English-speaking beach oasis with a colourful community feel and smack on the Hemisphere’s longest coral reef system.
Abaco
It’s close to the United States with an established real estate product. This is a 120-mile-long archipelago all in itself, a part of the Bahamas that’s long been a kind of haven for yachters, sailors and beach explorers. This is a place to get away from it all without being too far from it all.