Logo for Oyster Crew

CAPTAIN & STEW COUPLE TEAM | 2:2 ROTATION

Role overview

Qualifications

  • Yachtmaster Ocean or Master 200 minimum
  • Strong engineering background and happy to get hands-on
  • Previous cruising and racing experience
  • All relevant STCW and ancillary certifications

Responsibilities

  • Join a busy private sailing programme with a focus on racing and cruising
  • Participate in Caribbean regatta and the Oyster World Rally
  • Ensure high standards of cleanliness, presentation and professionalism
  • Work effectively as part of a team and maintain a positive attitude

Key facts

  • Remote from: Anywhere
  • Full time
  • English

Hard skills

Other skills

  • Detail Oriented
  • Cleanliness
  • Presentations
  • Professionalism
  • Proactivity
  • Adaptability

About the company

Oyster Crew logo

Oyster Crew

Staffing & Recruiting

Oyster Yachts was founded in 1973, rapidly establishing an international reputation in the sailing world for performance, quality, comfort and safety. Since new owner and CEO Richard Hadida took the helm in 2018, the company has gone from strength to strength; our first new model, the Oyster 565 won the Bluewater Cruiser of the Year at the British Yachting Awards in 2019Our mission is simple: to design, build and support the finest bluewater sailboats, capable of sailing safely anywhere in the world, in comfort and luxury.At the heart of Oyster are the people: those who design and build them and those who own and love them. Along with Oyster owners, we see ourselves as a family, inspired by each other, the stories we tell and the adventures we have.We are always on the look out for good quality crews to match to our fleet of yachts and owners. Whether it’s adventuring in high latitudes, family cruising around the world or chartering in the Caribbean and Mediterranean, there are plenty of amazing opportunities for aspiring Oyster crews and for those crews already in the Oyster family who are looking to take the next step. If you think you have what it takes, we really look forward to meeting you very soon.

Company details

Company typeSME
IndustryStaffing & Recruiting
Company size201 - 500

Your match analysis

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.

Job description

This is a remote position.

CAPTAIN & STEWARDESS COUPLE (2:2 ROTATION) | MED, CARIBBEAN & OYSTER WORLD RALLY

We'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. 



Requirements

Captain Requirements:
  • Yachtmaster Ocean or Master 200 minimum
  • Strong engineering background and happy to get hands-on
  • Previous cruising and racing experience
  • Experience running larger yachts with strong superyacht standards
  • Organised, proactive and confident leading a programme
Stewardess Requirements:
  • Loves sailing and being involved on deck, not just interior duties
  • Excellent attention to detail and housekeeping standards
  • Positive, upbeat and adaptable
  • Comfortable in both guest-facing and hands-on sailing environments
Requirements For Both:
  • All relevant STCW and ancillary certifications
  • B1/B2 visa preferred (can be arranged for the right couple)
  • Experience on larger sailing yachts
  • High standards of cleanliness, presentation and professionalism
  • Looking for a long-term position rather than just another season
  • Strong team players with a super positive attitude
  • We are considering couple teams due to ease of cabin arrangements.
This isn't just another crew job. It's a chance to join an ambitious sailing programme with exciting plans ahead, a great team around you, and owners who genuinely appreciate exceptional crew.

TOP TIPS BEFORE APPLYING:

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:

• Keep your CV clear, professional and ideally no more than 2 pages
• Include a short profile/objective section about yourself
• Add all relevant experience, qualifications, skills and contact details
• Include at least 3 written references where possible
• Chefs - please include a food portfolio (your own work only please) and any relevant Instagram links
• Upload all relevant and valid certificates as PDFs

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.



Apply once. Then go straight to the hiring manager.

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.

MR

Marcus Rivera

Chief Revenue Officer

m.rivera@company.com
linkedin.com/in/marcusrivera
Unlocked after you apply
·

Related jobs

Other jobs at Oyster Crew

Premium

Reach out to the hiring manager directly.

Gain access to the contact details of the hiring managers who actually decide, and reach out to network with them directly. That, plus more when you upgrade:

  • Full match report with fit score and gaps
  • Career diagnostics on how recruiters read you
  • Curated company matches and warm intros
  • 48h early access to new roles

Cancel anytime.