Position Title: Yacht Captain
Location: Florida (Winter) & Shelter Island, NY (Summer)
Schedule: Full-Time, Year-Round (Seasonally Based)
Employment Type: Open to Contractor or Employee (Client is flexible)
Housing: Provided while in Shelter Island, NY
Position Overview
The principals are seeking an experienced, responsible, and professional Yacht Captain to oversee a small private fleet and lead a respectful, policy-driven crew. The role is split seasonally, with approximately half the year based in Florida (including travel to the Bahamas and surrounding islands) and half the year in Shelter Island, NY, where vessels are primarily used on weekends and for leisure cruising.
This is a hands-on leadership role suited for a Captain who values structure, accountability, and professionalism, and who can successfully manage both vessels and crew in alignment with the family’s expectations.
The fleet is actively used during the winter season in Florida and the Bahamas, and more lightly during summers in Shelter Island.
Key Responsibilities
Vessel Operations & Navigation
- Captain and operate vessels safely and professionally in U.S. and international waters
- Plan and execute cruising itineraries in Florida, the Bahamas, and nearby islands
- Ensure all vessels are operated in compliance with maritime regulations and flag requirements
- Maintain readiness, cleanliness, and mechanical integrity of all vessels
Crew Leadership & Oversight
- Lead and manage a small boat team currently consisting of two captains and one stewardess
- Enforce onboard policies, procedures, and standards consistently
- Establish clear expectations around conduct, spending, and use of stipends
- Foster a respectful, professional crew culture aligned with the principals’ preferences
- Provide feedback, structure, and accountability to ensure rules are followed
Maintenance & Logistics
- Oversee routine maintenance, servicing, and repairs across the fleet
- Coordinate with vendors, marinas, and service providers
- Ensure vessels are properly provisioned and stocked according to approved guidelines
- Manage seasonal transitions between Florida and Shelter Island
Owner Experience & Discretion
- Ensure a seamless, stress-free boating experience for the principals and their guests
- Respect privacy, confidentiality, and household policies at all times
- Act as a trusted representative of the principals when managing crew, vendors, and marinas
Qualifications & Experience
- Prior experience as a Yacht Captain on private vessels (50’+ preferred)
- Strong leadership and crew management skills
- Comfortable operating in both U.S. and international waters
- High level of professionalism, integrity, and rule adherence
- Ability to manage multiple vessels and rotating usage schedules
- Flexible and adaptable to seasonal travel and changing itineraries
- Experience operating foreign-flagged vessels strongly preferred
- The primary vessel is Jamaican-flagged; Captain must hold internationally recognized certifications compliant with Jamaican Maritime Authority requirements
Additional Notes
- Long-term opportunity for a Captain seeking stability and a respectful working environment
- The ideal candidate values structure and understands the importance of boundaries, accountability, and professionalism in a private setting