“One day I want to live in the Caribbean.” It’s a dream everyone has at one time or another — but choosing to live on a small island is that much more romantic; it’s a decision more about the heart than the head, about finding your own tiny paradise. There’s something special about a small island — and while the experience won’t quite be what you’ll find on larger Caribbean islands, you don’t necessarily have to compromise everything. For this list of the Best Small Islands to Live On, we looked at small islands that had the right mix of scenery, culture, activity, development and convenience, considering factors like healthcare, cost of living and transportation, and then narrowing the list to those islands with a population of less than 12,000. So here it is: whether you’re moving or simply looking to buy a vacation home for longer stays, these are the Best Small Islands to Live On in the Caribbean.
St John
It’s small, it’s beautiful, it’s a US territory … St John isn’t just a marvelous place to visit — it’s a wonderful small island to live on, from the funky, artistic environment to the carefree vibe to the convenience of having St Thomas just a short ferry ride away. There’s a reason expats head to St John — it’s a great all around island to live on.
St Barth
The island’s very high costs are the only thing keeping it from the top spot here, as this small jewel of the French Caribbean has just about everything you want: culture, terrific restaurants, beautiful villas, great beaches, a cosmopolitan community and, oh yeah, the best supermarkets in all of the Caribbean.
Vieques
Like St John, this is part of the US, meaning for US citizens this is an easy move. And once you get here, you’ll fall in love with the ultra-laid-back lifestyle, the endless beaches, the wild horses and the food. There’s a great expat community here, too, making integration that much easier.
Culebra
Even smaller than its neighbor in Puerto Rico, this is for the more adventurous, but the payoff is big. From world-famous Playa Flamenco to a growing cultural community (and new nightlife), this is the essence of Puerto Rico.
Terre de Haut
Think a smaller, more affordable version of St Barth, with the same French Caribbean charm and topography. The best-kept secret in the Eastern Caribbean, this tiny island in the Guadeloupe archipelago has a thriving culinary scene and is a haven for naturalists.
Virgin Gorda
While it’s the most upscale island in the British Virgin Islands, Virgin Gorda is also decidedly low-density, from its small hotels to its beaches. But thanks to its North Sound, this is the place to move if you’re a boater in search of small island.
Bequia
The coolest place in the Grenadines is also its coolest place to live, with an always-funky environment and a lovely mix of locals and expats passionate about the Caribbean. And given its location, it’s an island hopper’s delight, along with being a short flight from Barbados.
Saba
No, there aren’t any beaches, but this is as lovely a place to be as there is in the Caribbean, thanks to Dutch influence and an Old Caribbean mentality. Saba, just a short flight (or ferry) from St Maarten, is an island right out of a storybook. But it’s no fairytale — you can live here, and do so comfortably in the kind of setting that really doesn’t exist anywhere else in the region.
Eleuthera
One of the Bahamas’ more elegant destinations is another thriving real estate market, thanks to beautiful, decidedly untouched beaches. If you’re looking for a small island with opportunities to build or buy a home on the beach, this is it. It’s easily one of the Best Small Islands to Live On.