Boat Captain

ISLAND MANAGER & YACHT CAPTAIN

Private Family Estate – Maine & U.S. Virgin Islands

A private family seeks a highly capable, hands-on professional to serve in a dual seasonal role:

• May–October: Island Manager of a 37-acre private estate in Castine, Maine
• October–May: Captain of a 63’ Hatteras motor yacht based in the U.S. Virgin Islands

This is not a clock-watching job. It is an ownership mindset role.

We are looking for a long-term steward who takes pride in readiness, order, and quiet excellence.

THE ROLE

Island Season (Maine – May through October)

• Maintain all residences, grounds, docks, and infrastructure to first-class standards
• Oversee housekeeper, chef support, and grounds staff
• Coordinate provisioning and assist chef as needed
• Manage vendors and maintenance
• Ensure safety protocols and property security
• Perform detailed accounting tracking with New Orleans accounting staff

Yacht Season (Caribbean – October through May)

• Captain and operate 63’ Hatteras motor yacht
• Maintain all systems to true “game-ready” condition
• Perform onboard cooking and provisioning
• Handle all yacht laundry and guest readiness
• Maintain logs, maintenance schedules, and safety compliance
• Ensure vessel is never unattended for more than three weeks

WHAT “GOOD” LOOKS LIKE

The right candidate:

• Leaves nothing half-done
• Is comfortable being solely responsible for high-value assets
• Plans time off around readiness — not the other way around
• Asks for approval before scheduling time away
• Communicates clearly and early
• Presents problems with solutions
• Is systems-oriented and disciplined

If the owner showed up unannounced, the boat and island would be ready.

WHAT THIS ROLE IS NOT

• Not a rotational crew job
• Not a seasonal hobby position
• Not a “lifestyle” posting
• Not suitable for someone who needs constant direction

This is a professional stewardship position requiring maturity, judgment, and personal accountability.

REQUIREMENTS

• Proven experience captaining similar-sized motor yachts
• Strong mechanical aptitude and troubleshooting ability
• Comfortable cooking and managing onboard hospitality
• Experience overseeing property or estate operations preferred
• Clean record and professional references
• Willingness to reside in Castine, Maine during island season

COMPENSATION & BENEFITS

• Competitive salary (commensurate with experience)
• $3,000 annual travel allowance
• All meals covered while on the yacht
• Seasonal housing provided

IDEAL PERSONALITY

We value:

• Calm competence
• Humility
• Discipline
• Pride in quiet excellence

We do not value:

• Drama
• Excuses
• Blame
• Entitlement

TO APPLY

Please submit résumé, references, and a short statement describing how you define a vessel being “game-ready.”

Salary : $100,000