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.
Start a Boutique Hotel
While this is incredibly hard work, this has two major benefits: one, your office is the Caribbean, and two, you’ll be providing employment for locals — meaning you won’t just be spending a “retirement” — you’ll be helping the local economy. And there are loads of hotels currently on the block in the Caribbean, particularly small boutique properties, particularly on islands like Puerto Rico and in the Dominican Republic. For a place full of smaller, more affordable lots, try Dominica, the “Nature Island,” with dozens of tucked-away properties perfect for a “starter” hotel, like the one above, which is currently on the market. On a smaller scale, you can even turn your home into a bed-and-breakfast, opening up the options to more islands across the region.
Cruise the Caribbean
Another Caribbean fantasy: spending your days living on a sailboat, navigating the Caribbean. More and more people are doing it, and with the right financial head start you can do it, too. The best places to begin looking? St Vincent and the Grenadines, the British Virgin Islands and the Out Islands of the Bahamas, particularly the Abacos. And then there’s the extra option: chartering your boat for additional revenue.
Be a Divemaster
Why not spend your retirement under the sea — or teach others how to get there? Head to Bonaire, grab your gear and get into the water. This is the best place in the Caribbean whether you’re a beginning diver or more advanced, and you can take all levels of coursework to complete your journey at outlets like the Buddy Dive Resort.
Work in the Art World
The world is increasingly appreciating the talent and creativity of the Caribbean’s art scene, and there are scores of terrific galleries around the region, from the Colonial Zone of Santo Domingo to Martinique. The only question is whether you want to explore your own creativity (there’s a reason so many great artists have gone to the Caribbean to find inspiration) or work in a gallery, even as a volunteer. Great starting points? The Dominican Republic and the growing art hub of St John in the US Virgin Islands.
Learn to Cook
Caribbean cuisine is increasingly going global. And that’s because it’s a compelling mix of European, Asian and African flavors, and because there is an impressive collection of world-class Caribbean chefs on the scene. So why not become one of them? There are all kinds of ways to learn cooking in the Caribbean, whether you take classes at hotels like Cobblers Cove in Barbados or Graycliff in Nassau (home to its own “Culinary Academy.” For a more formal take, try culinary schools like the Jose Santana International School of Hospitality and Culinary Arts in Puerto Rico.
Be an Environmental Volunteer
Just about everyone who comes to the Caribbean is coming largely for one reason: the natural beauty of the region. So why not give back and help protect it? Spend your retirement as an environmental volunteer. And there are so many great ways to do it, whether you’re protecting sea turtle nests in Nevis (with the Nevis Turtle Group) or protecting the Green Caribbean with Friends of Virgin Islands National Park in St John.
Go Back to School
Why not go to school in the Caribbean? There are some great universities in the region, both medical schools and larger universities, with tuitions far lower than their counterparts in the United States. So why not get a Master’s Degree in environmental engineering, or biodiversity education or even renewable energy? The University of the West Indies has campuses across the Caribbean, with the oldest and most famous the Mona Campus in Jamaica. Or for a broad, affordable mix of undergraduate classes, try the University of the Virgin Islands.
Become a Tour Guide
Tourism is the Caribbean’s largest economic driver — and that means that getting tourists to come back after the first visit is a big priority. So why not improve their experience by becoming a tour guide? That can mean many things, whether you’re working at a local historical society, helping out the local tourism office or even working as a tourism ambassador. Where should you look? The Cayman Islands, Puerto Rico and the US Virgin Islands would be great starting points.
Become a Charter Captain
Maybe cruising alone isn’t for you. Maybe you want to be even more active — like becoming a charter captain. Charter captains don’t just navigate — they’re ambassadors of the Caribbean, pathways to unforgettable Caribbean trips. If you’re already an experienced sailors, the best way to begin is by looking for large charter companies for experience, like The Moorings in the British Virgin Islands.