Captain - Permanent - Min exp 5 years - General (Caribbean)
Captain / Mate Couple — Private Liveaboard Sailing Yacht (Oyster 595)
Caribbean, US East Coast & New England — December 2026
A highly specified Oyster 595, currently enjoying her first Mediterranean season, is seeking a captain/couple to join her owner for an exciting 2027 program on the other side of the Atlantic.
THE YACHT
The yacht is a serious bluewater vessel maintained to a high professional standard, with full offshore equipment, modern systems, and an actively involved owner with growing offshore experience. She is operated under Cayman Islands registry with professional crew employed on MLC-compliant Seafarer Employment Agreements.
THE 2027 PROGRAM
Beginning in St. Lucia in December 2026, the program for 2027 is as follows:
• Caribbean exploration expected to include: St Lucia, Martinique, Grenada, Guadeloupe, Montserrat, St Kitts, Antigua, St Barts, Sint Maaten, BVI and Oyster Antigua Regatta (January through May 2027)
• Depart Caribbean with passage north ahead of hurricane season, (May)
• New England summer cruising, including Maine and Nova Scotia (June-October)
• Newport, Rhode Island (USA) for haul-out and planned upgrades during hurricane season
• Likely return south to the Caribbean, late 2027 or early 2028
Looking further ahead, a Panama Cancel transit and Pacific cruising in 2028 is part of the owner's broader vision.
THE ROLES
Captain
The captain will have full responsibility for the safe operation, navigation, and seamanship of the vessel. The owner is actively involved in sailing and passage planning and expects a collaborative, professional and friendly working relationship. Strong systems knowledge and the ability to manage maintenance, warranty, and refit coordination on a modern offshore sailing yacht are essential. The captain is expected to be a hands-on working skipper — comfortable with routine maintenance, systems troubleshooting, and keeping the vessel in first-class condition as a matter of professional pride, with third-party contractors used where genuinely necessary. Experience with high-specification bluewater sailing yachts from premium builders is preferred. RYA Yachtmaster Offshore Commercial (or equivalent) is required; Yachtmaster Ocean is preferred. Minimum five years’ experience, with demonstrated bluewater offshore passage-making.
Mate / Crew
The partner role on this yacht is broad and genuinely central to the onboard lifestyle. In addition to normal watch-keeping and seamanship duties, the mate will take primary ownership of provisioning and galley operations — planning, sourcing, and preparing meals as the principal cook for the vessel — with active support from the owner. This is not a charter steward role; it is a collaborative, live-aboard environment with an engaged owner who participates actively in all aspects of boat life. The right candidate will take genuine pride in running well-provisioned boat and will adapt this role as needed with changing circumstances. RYA Dayskipper or equivalent watch-keeping qualification is required; higher certifications are welcome.
THE ENVIRONMENT
This is a private live-aboard program — no charter guests, no rotation schedule, no corporate yacht management overlay. The owner strives to live aboard full time and expects to be present for the majority of passages and anchorages. The owner is experienced in managing professional crew and operates within a structured SEA framework with transparent compensation, bonuses, paid time off, and professional development support. The goal is a small, cohesive team that sails well, lives well, and takes genuine pride in the vessel.
The crew cabin is a private double for the couple's exclusive use.
COMPENSATION
Competitive and commensurate with experience and role. Package includes MLC-compliant Seafarer Employment Agreements, private double cabin, and all living expenses aboard. Details discussed with serious candidates.
APPLYING
Applications from captain/couple combinations are preferred, though exceptional individual captains who can suggest a qualified partner will be considered. Please include a brief covering note describing your background, your partner's background and relevant experience, including why this program interests you. CVs with certifications and references for both individuals are required.
Experience in Caribbean waters and/or US East Coast cruising is a strong advantage. Candidates with ARC or offshore Atlantic passage experience are especially welcome.
Close