Job Description

Job Location: Premium Parking Miami FL - Miami, FL 33131
Position Type: Seasonal
Salary Range: $100,000.00 - $100,000.00 Salary/year
Job Shift: Varies
Job Category: OtherISLAND 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.

QualificationsREQUIREMENTS
- 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.”