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Which Caribbean Island Should You Retire to?

Photo by EpicStockMedia via Shutterstock
Written by Chris Osburn

This blog post was updated on August 17, 2021.

If you’re starting to plan ahead for retirement and wonder just how far your money can go in the Caribbean, then this list is for you. If you’re trying to decide between cruising to Curacao or hopping on flights to Bahamas to spend your well-earned retirement, then read on to find out about what to consider before committing to your ideal locale.

New Providence


Although not the largest, New Providence is the most populated island in the Bahamas, with 250,000 residents. Most of those people live in Nassau, the Bahamas’ only real city. Turquoise waters, pink beaches, close proximity to Miami, and year-round great weather make it a top choice (if not necessarily the most budget-friendly option) for superlative seaside senior living.

Looking for some cheap flights to Bahamas? Check out these limited-time fares that can help you save on your trip!

Ambergris Caye

Scuba diver at coral reef in Belize

The largest island off the coast of Belize, Ambergris Caye is an ideal spot for settling down if you want to maintain an active lifestyle after you retire. Owing to a spectacular coral reef about a half mile offshore, the island’s only town San Pedro (population: 12,000) is a hub for diving, deep-sea fishing, sailing, and a range of other watersports. English is spoken throughout the island, as is across much of Belize. Golf carts are the preferred mode of transport for most expats (there are about 20,000 living on the island, many of whom are retirees). The cost of living is about as low as it gets for island living without leaving the comforts of civilization. There’s a good variety of shops, clubs, restaurants, bars, and cafés, though some people relocating to Ambergris Caye might miss certain amenities from “back home.”


On the beach in Curacao
is the biggest and most populous island of the Netherlands Antilles (even though its population numbers only 160,000, with most residents clustered around the colorful colonial city of Willemstad). The island’s unique cultural blend of Dutch and African with strong elements of Sephardic Jewish, Indonesian, and Chinese influences makes it a distinctive and fascinating place for a vacation, second home, or retirement destination. Situated outside the hurricane belt, Curacao has a short rainy season (October to December) and an exceptionally dry climate for the Caribbean. Most people speak English (though it isn’t the first language). Taxes are low. Direct flights to major airports in the US are short, plentiful, and affordable.

Dominican Republic


So first of all the Dominican Republic isn’t an island. It’s a country on the eastern side of the island of Hispaniola (the western side is the country of Haiti). But as far as all the other components for being a tropical island paradise for your retirement, the DR fits the bill. It’s super affordable for most Americans, even with modest pensions or savings. The weather’s great, while the golfing, beaches, cuisine, and nightlife are among the best in Latin America.

RELATED: If enjoying a glass of rum on those lazy days on the beach are part of your ideal retirement, then you must read A Rum Lover’s Guide to the Caribbean!

Puerto Rico

Couple in Puerto Rico

As Puerto Rico is a territory of the United States, moving there is as easy as moving to any of the 50 states. Here’s where you’ll have access to most amenities from the mainland. But it’s worth noting that certain samples (cheese, milk) will cost more than you might be accustomed to paying. Property prices and taxes are especially low though. There are great flight connections to anywhere in North America, crime is low, the beaches are amazing, and the weather is gorgeous.

Retiring to the perfect paradise island can actually be easier than you think. But remember: Before you catch flights to Bahamas or dive into the Dominican Republic to start a new exciting chapter of your life, make sure you choose your new home wisely!

Do you dream of retiring to an island in the Caribbean? Tell us about your retirement goals in the comments.

About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

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