The Best Caribbean Islands to Retire To

Sometimes you go to a Caribbean island and wish you didn’t have to leave. (Or perhaps in your case it’s all the time). These are the kind of islands you know you could live on permanently or already do.  More and more, that’s a decision people from all around the world are making — particularly when it comes to retirement. There are a number of islands across the Caribbean that are great for spending your retirement — and we’ve brought you our top recommendations, looking at factors like standard of living, affordability, healthcare, financial incentives, security and arts and culture. So perhaps next time you’ll pack your bags, head to the airport, and never return.


This Dutch Caribbean island has just under 17,000 people, but it’s home to great food, European infrastructure and, more importantly, it’s outside of the Hurricane Belt. It’s a place to pursue your passions, from gastronomy to art to windsurfing, with some of the friendliest people anywhere in the Caribbean. It also boasts very competitive real estate pricing by Caribbean standards.

Grand Cayman

More than just a financial capital, Cayman has excellent food, tremendous beaches, no property taxes and, most notably, recently debuted the Caribbean’s most cutting-edge health facility, Health City.

St John, US Virgin Islands

This lush paradise is almost 60 percent national park, with very good housing opportunities, a funky vibe, beautiful beaches and great access to a number of nearby islands so you can spend your retirement island-hopping.


It’s called One Happy Island for a reason. This Dutch island has an international flavour, gorgeous beaches, is outside of the Hurricane Belt and is also one of the most environmentally-friendly islands in the region.

Ambergris Caye, Belize

This island on the Caribbean coast of Central America has long been a magnet for expatriates, and that’s made it an even better retirement destination. It’s centrally located, with a spectacular offshore reef making for some of the Caribbean’s best diving and its more affordable cost of living a major plus.

Abaco, Bahamas

This is the place to retire if your dream is to leave everything behind and head out for an island. There’s great sailing, fishing and beaches and a brand-new airport terminal at Marsh Harbour for easy access in and out.


This cosmopolitan island in the Turks and Caicos has a huge stock of beachfront condominiums on a world-class beach, excellent restaurants and easy, short direct flights to and from the US mainland. And there are no property taxes.

Puerto Rico

More and more hedge funds and US investors are coming here thanks to a host of special tax incentives. Puerto Rico has a vibrant culture, great beaches and golf, and its capital, San Juan is a Caribbean cosmopolis — an energetic place to spend your retirement, surrounded by the sea. The island’s been in a debt crisis, but more and more, that’s making people see it as an opportunity. It also has one of the Caribbean’s highest life expectancies.

Cap Cana, Dominican Republic

An exclusive corner of the island of Hispaniola, this luxurious enclave of the Dominican Republic has abundant sunshine, great infrastructure, an even better marina and very good culinary scene. Not to mention some of the best golf in the Caribbean.


Instead of spending your dream retirement in the South of France, why not head to France’s outpost in the Caribbean? This island is home to incredibly good food, some of the best infrastructure anywhere in the Caribbean (and the best roads), along with French-level healthcare, and is one of the region’s safest places. And as for new passions to pursue, why not try its 11 rum distilleries?

Virgin Gorda

This British Virgin Island is home to some great real estate opportunities. Yes, you can leave it all behind to come here, but you won’t be compromising too much because of the high standard of living and great island hopping. If you’re a retiring yachter or sailor, this is the place for you — there’s some of the best sailing in the world.


If you want to get away from the hustle and bustle and find an untouched, different way of life, Nevis is the place. There’s beautiful nature and hiking, a charming little main town, a superb golf course and some of the Caribbean’s friendliest people. It’s off the beaten path, but there’s easy air access just a boatride away in St Kitts. Crucially, you can also earn citizenship by investing in the country through the Citizenship by Investment programme.


The island’s proximity to the US mainland means it’s really easy to get back and forth, but Nassau (actually the island of New Providence) is also a vibrant place, with a great collection of restaurants, excellent shopping and a burgeoning arts scene. And its abundant white-sand beaches mean there’s likely an empty beach for you almost every day of the week.

Source: Caribbean Journal – October 22nd, 2014

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