Retiring to the Caribbean


Everyone dreams of retiring in the Caribbean. And the ultimate dream is retiring to a small, far-off island away from the hustle and bustle of the world. Retirement in the Caribbean certainly has its share of sacrifices and challenges, and that’s particularly true on a small island. But what you get in return is total independence, umatched relaxation, island charm and a completely different rhythm to your days. Another unheralded benefit is you really become part of a community, something that isn’t necessarily true in many larger “retirement” destinations. These are the small islands we think are the best starting points to make a decision like this — they’re small, they’re beautiful and they’re not really like anywhere else.

Bocas del Toro, Panama
Panama has become one of the world’s hottest destinations for retirees, especially from the US. That’s in large part due two factors: the country’s pensionado programme, which offers retirees a series of discounts on everything from medical exams to entertainment, and a cost of living that’s among the lowest of any destination in the region. And Bocas del Toro is full of tiny islands to choose from, from the “main” island of Isla Colon to the popular Red Frog Beach development on the island of Isla Bastimentos.

Treasure Cay, Bahamas
This island in the Abaco chain of the Bahamas has it all: some of the best beaches in the Caribbean, a surfeit of real estate for sale, both in condominiums and lots, easy access both through nearby Marsh Harbour (an international airport) and its own small strip. There’s also a great marina if you want access to the Bahamas’ spectacular waters.

Virgin Gorda, British Virgin Islands
There’s a great real estate product here in developments like Oil Nut Bay and Nail Bay. This is definitely a place for a luxury retirement, with great access to the boating and sailing lifestyle, easy access to many of the other Virgin Islands and the feeling of a high standard of living. (There’s an airstrip, too, just in case you need it).

Bequia, St Vincent and the Grenadines
This is the coolest island in the Grenadines, an amalgam of cultures and generations; in part due its whaling history, there’s a bit of a vibration here of New England, which makes for a rare ambience that’s tough to find in the Caribbean. This is an artsy, funky place with a small town feel but also with a way of reinvigorating its residents and visitors.


One of the Caribbean’s best retirement destinations of any size, this Dutch Caribbean island has a close-knit feel, with a significant expat community that makes new arrivals feel welcome almost upon touching down on the plane. And it’s a place to learn new things, whether you’re diving, windsurfing or speaking a new language. It’s also a great jumping off point if you want to spend your retirement on excursions to nearby South America.

St Barth
Almost certainly the most expensive retirement in the Caribbean, but there’s a reason: you get what you pay for: some of the Caribbean’s best food, spectacular villas to choose from, very few cruise passengers to deal with, great shopping and a thriving French-Caribbean culture. There’s ferry and air access to St Martin, which provides a great weekend destination in its own right.

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  • Enigma Yachts Limited
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  • London Fractions
  • Cyan International Properties
  • QTD
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  • Jumeirah
  • Alexander James
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  • Cornerstone Tax Advisors
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  • Dominic McKenzie Architects
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