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:

• MayOctober: Island Manager of a 37-acre private estate in Castine Maine
• OctoberMay: 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)
• $3000 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.