The Cayman Islands Are Hiring a Chief Relaxation Officer

What Is the Chief Relaxation Officer Role

The Cayman Islands Department of Tourism created the Chief Relaxation Officer role to tackle a modern problem: vacations that are packed with alarms, itineraries, reservations, and the pressure to document every moment.

The CRO’s mission is refreshingly simple. Spend two weeks in the Cayman Islands slowing down on purpose. No schedules. No hustle. No FOMO. Just intentional rest and island time, modeled in a way that shows travelers how restorative a vacation can actually be when you stop trying to optimize it.

This role is part of the Cayman Islands’ broader “vaCay” philosophy, which treats rest not as a reward, but as a way of life. It’s about doing less, intentionally, and letting the destination do the work.

The “Job Description” (Yes, This Is Real)

The official responsibilities read less like work and more like a gentle reminder of how humans are supposed to exist.

Your duties include:

• Sleeping at least eight hours a night, with naps strongly encouraged

• Spending time by the water every day, floating, reading, or doing nothing at all

• Eating fresh local dishes like coconut ceviche

• Sipping island cocktails at iconic beachfront spots

• Dining with locals to learn their relaxation rituals

• Exploring nature and spotting rare island species like the Blue Iguana and Cayman Parrot

• Ending each day with a tech-free sunset on the beach


These are not perks. They are requirements.

What the Winner Gets

The Chief Relaxation Officer will enjoy 13 nights split between two standout properties: The Westin Grand Cayman Seven Mile Beach Resort & Spa and Le Soleil d’Or.

The prize package includes:

• Round-trip coach airfare to Grand Cayman

• Round-trip inter-island flights to Cayman Brac

• On-island transportation

• A daily stipend for meals and optional experiences

• Up to three curated experiences

• A custom “no-itinerary itinerary” created by the Board of Relaxation


Yes, a Board of Relaxation is involved. And yes, that might be the best part.

Meet the Board of Relaxation

Applications are reviewed by the Board of Relaxation, a group of Cayman locals who genuinely live the slow-island philosophy. Made up of hospitality leaders, restaurateurs, wellness experts, and community figures, the board is looking for the applicant who needs this reset the most and is willing to fully embrace it.

This is not about having the best resume. It is about being ready to stop rushing.

How to Apply

To apply, travelers are asked to submit their “worst vacation ever” story. Think missed connections, overpacked itineraries, family meltdowns, or trips that somehow felt more stressful than staying home.

Submissions may include video and must be submitted through the official Cayman Islands tourism website.

Requirements to Apply (Read This Before You Start Writing)

Before you draft your “worst vacation ever” story, here are the key eligibility rules you actually need to know:

• You must be a legal resident of the United States or Washington, D.C.

• You must be 21 or older at the time you enter

• You must have a valid government-issued photo ID

• You must have (or be able to obtain) a valid passport that will be valid for at least six months after your return date

• You can submit one entry per person

• Your story must be submitted as text (up to 350 words) and/or a short video (up to 15 seconds)

• Entries close February 17, 2026 (11:59 pm ET)

• The prize is for the winner only (no guest), and travel must be completed by June 30, 2026


That is the important stuff. The rest is fine print.

In a world obsessed with productivity, the Cayman Islands are betting that the most aspirational travel experience right now is learning how to truly slow down. If you have ever come home from vacation needing another vacation, this might be your sign — preferably written in the sand, not your calendar.

FAQ: Chief Relaxation Officer

Is the Chief Relaxation Officer a real job?


It is a real promotion run by the Cayman Islands Department of Tourism, but it is not employment. It is a promotional contest and travel prize package.

Who can apply?


The opportunity is open to U.S. residents aged 21 and over with a valid passport.

What does the winner receive?


Flights, inter-island travel, 13 nights of accommodations, a daily stipend, on-island transportation, and a schedule-free itinerary.

How do you apply?


By submitting your worst vacation story at visitcaymanislands.com/ChiefRelaxationOfficer.

When is the deadline?


Applications must be submitted by February 17, 2026.