The 10 Best Ways to Retire in the Caribbean

Retiring well is a subjective matter. For some it’s time to kick back and watch the world go by. For others it’s time to put it into high-gear and create an altogether new life. There are many stories about people who have either retired and expatriated to the Caribbean and are living well. But everyone’s experience is different. That’s why we’ve given you starting points and ideas — hopefully inspiring you to take the next steps toward your dream retirement.

Just like saving takes time, so does planning. Some of these ideas will even take training and experience, and you’ll need to think about everything from funding to visa issues to business licensing. Some islands are more business and employment-friendly than others, particularly for expats, but determined people can find these opportunities on just about any island. And before you pull the trigger you’ll need to visit at least two to three of the most appropriate places for the kind of lifestyle you are seeking. Here are 10 ways to spend your retirement doing a dream job.

Run Your Own Beach Bar

There a few more popular dreams in the Caribbean than running your own beach bar. It isn’t as easy as it sounds, but it can and is often does happen, especially in islands with business-friendly economies. This isn’t a job — it’s a lifestyle, with challenges from seasonality to marketing, whether you’re a bartender or you’re starting your own bar. And of course you can find infinite inspiration in the story of O’Connell, the expat who now manages the world-famous Soggy Dollar Bar in Jost Van Dyke. Some of the best places to start looking? Beach-heavy Anguilla, beach-bar friendly British Virgin Islands and the Out Islands of the Bahamas.