Upgrade: 3 fabulous — and affordable — Caribbean island locales for retirees

The perks of retiring to a Caribbean island — the warm weather, the laid-back lifestyle and the gorgeous surroundings — are as clear as the waters you’ll be swimming in there.

“I am in paradise,” says 76-year-old Julie Lea, who moved to Bequia in the Grenadines from Waterford, Va., with her husband in 1999. Lea, an artist who began visiting the tiny island in the late 1970s with her family, says the colors — the teal of the sea, the hot pinks and yellows of the flowers, the sometimes fierce sun bathing the land in light — drew her in. “I finally found a place where I could paint bright colors right out of the acrylic tubes, where I didn’t have to tone them down,” she says. “Virginia is misty and quiet and ladylike; here’s it’s wild.”

For Casey Callais, who left Beaumont, Texas, in 2008 to pursue volunteer opportunities on the Caribbean coast of Nicaragua, the people were a big draw. “There’s an openness and friendliness to the local people,” he remarks. “They do more than just say hi — they say hi, invite you into their home, cook for you, invite you to stay with them.”

But behind that friendly, postcard-perfect veneer, there are plenty of downsides to retiring in the Caribbean islands, among them health-care options that are often mediocre (typically you must travel to a large city to find a full-scale hospital), hurricanes, sketchy infrastructure, high prices for food and other staples, and language barriers. “Because they’re islands, they tend to be small and limited,” says Kathleen Peddicord, the publisher of Live and Invest Overseas. “If you don’t bring it with you, it might not be there.”

That means, for many, boredom: “If you are happy to swim, snorkel, fish, dive and lay in the sun, then the Caribbean is for you,” she says. “But if that only sounds fun for a while, then maybe not.”

Or, you may, as Lea does, need to make a lot of your own entertainment, as there may not be a ton of shopping and entertainment on the island you choose. She writes books, paints (and sells her work at a studio in town), teaches watercolor classes and gardens. And you can’t always fall back on TV and the Internet: “Internet access is slow at best,” Callais says. “A lot of people live a very unplugged or slowly plugged life.”

Retiring in the Caribbean can also be incredibly pricey. Beachfront properties on posher and more popular islands such as St. Barts and Anguilla often go for millions of dollars. When you add up your housing, travel costs and the premiums of island living (many items, from food to electronics, have to be shipped in), retiring to the Caribbean can take a toll on one’s retirement nest egg. Plus, there are residency and administrative issues (like getting your Social Security check and banking) to consider — all of which can be a hassle.

The good news: Those looking for that quintessential, Caribbean island lifestyle in retirement — nice beaches coupled with good shopping, restaurants and housing stock, as well as plenty of expats to befriend — can still find it, and (relatively) affordably to boot.

Here are three places to consider…

This story was originally published in 2016.

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