Craving a little R&R? Perhaps lounging around on a beach with white, powdery sands, sipping cocktails in between dips in brilliant turquoise waters? For many, the price tag for that vacation may not be in the budget, but there is an exciting opportunity that will allow you to do just that as part of your job—and, it’s in the Cayman Islands!
If you’re the lucky chosen applicant, you’ll spend two weeks on Grand Cayman and Cayman Brac as the Chief Relaxation Officer, splitting your time between the Westin Grand Cayman Seven Mile Beach Resort & Spa and the boutique farm inn Le Soleil D’or.
It’s easy to get there with direct flights from a number of major U.S. cities, including Los Angeles, Denver, New York, and Miami. Even better? The flights there and back, plus your inter-island flights, are all included, so you don’t even have to worry about the cost of airfare.
Job Duties Explained
Your role as Chief Relaxation Officer is basically to chill and relax. Responsibilities include helping to redefine what it really means to take time off, doing less intentionally, with no schedule, no stress, just enjoying island time. Your “work” won’t entail catering to guests or any of those usual tourism tasks—it’s simply to show the world how slowing down can provide true restoration.
The specific job duties? Sleeping at least eight hours a night (naps encouraged) and spending time by the water every day doing whatever you’d like, whether it’s reading a good book, floating under the sun, or doing nothing at all. You’ll also enjoy fresh local dishes, sip island cocktails, explore nature, and get to know some of the rare wildlife species like the Cayman parrot. The grand finale to every day is a “tech-free” sunset on the beach. Yes, it’s all included as it’s part of your job! Your “no-itinerary itinerary,” as they call it, will be custom-designed by a Board of Relaxation.
What’s the Catch?
There’s really no catch, but before you get too excited, as you might imagine, you’ll probably be going up against thousands of other applicants. And, there are some stipulations: you must be at least 21 years old, a resident of the United States, and have a valid passport. Your application, submitted no later than February 17, 2026, will require sharing your worst vacation story online via the Cayman Islands official tourism site.
Time to think about all your past vacations and get those creative juices going! If you’re the “winner” of this job, you’ll have a blissful two weeks to look forward to.
