Find your next role
Strengthen your profile
Oyster Crew
Staffing & Recruiting
See how your profile stacks up against this role.
We compared the job requirements to your profile to show where you're strong and where you fall short.
This is a remote position.
CAPTAIN & STEWARDESS COUPLE (2:2 ROTATION) | MED, CARIBBEAN & OYSTER WORLD RALLYWe're looking for a brilliant Captain & Stewardess couple to join a busy private sailing programme that's got a lot to look forward to over the next few years.
The owners have completely fallen in love with racing, so alongside Mediterranean cruising, the yacht has a packed Caribbean regatta calendar and the Oyster World Rally ahead. It's a varied programme that mixes proper sailing, owner use, racing and adventure, with no two seasons looking quite the same.
Operating on a 2:2 rotation, you'll be joining a well-established team and a programme that's continuing to grow. Winters are spent in the Caribbean, summers in the Mediterranean, and there's plenty on the horizon as the owners continue to invest in both the yacht and the wider programme.
The yacht is currently in Newport, Rhode Island for her pre-winter yard period before heading south to the Caribbean in December. Start date is October/November 2026.
This would suit a couple in an established relationship who genuinely enjoy sailing life, take pride in what they do, and are looking for a role they can really make their own. Great owners, exciting plans, and the chance to be part of something for the long term.
If you’re genuinely interested in this role, take a moment to think about how you present yourself. At this stage, we only know you from your application - so make it count!
Please read the full job description carefully and only apply if you meet the relevant experience and certification requirements.
A few things that really help your application stand out:
Most importantly, complete your application properly through the system so we can review everything in one place.
⚠️ Please apply directly via the “I’m Interested” button only.
After you apply, unlock the direct contact details of the people who actually make the call. A quick follow-up makes you 5x more likely to land an interview.
Marcus Rivera
Chief Revenue Officer

Mercor

Really Great Reading

University of Miami

Tenet Healthcare

Solventum

Oyster Crew

Oyster Crew

Oyster Crew