Lead Captain

Company: Holoholo Charters

Location: Port Allen, Kauaʻi, Hawaiʻi
Compensation: Starting at $40/hour

About Holoholo Charters

Holoholo Charters is a locally owned and operated company that has been sharing Kauaʻi’s wild side with aloha for over 27 years. Based out of Port Allen, we provide unique catamaran tours along Kauaʻi’s iconic Nāpali Coast and beyond. With a variety of vessels, tour routes, and ocean experiences, Holoholo Charters is proud to have been voted the #1 Best Boat Tour in the U.S. by Newsweek Readers' Choice 2025.

Position Overview

Holoholo Charters is seeking an experienced and qualified Lead Captain to join our leadership team. This position is ideal for a skilled boat captain with strong knowledge of Kauaʻi’s ocean conditions, weather forecasting, vessel operations, safety standards, and team leadership.

The Lead Captain plays an important role in supporting safe, efficient, and high-quality daily operations. This position helps oversee captains and crew, maintain vessel standards, support training, assist with scheduling, and ensure company policies, procedures, and safety requirements are consistently followed.

Responsibilities

- Operate and navigate vessels in compliance with all safety regulations, company procedures, and maritime guidelines.
Ensure all safety equipment on board is properly maintained, accessible, and in good working condition.
Lead and manage boat crew by delegating tasks, supporting teamwork, and encouraging effective collaboration during daily operations.

• Supervise the training and development of new captains and crew members.
• Assist with creating crew schedules based on operational needs, crew availability, training requirements, and vessel readiness. -- ----- Submit schedules to the Operations Manager for final review, approval, and publishing.
• Maintain high standards for vessel appearance, cleanliness, organization, and overall upkeep.
• Perform routine maintenance tasks and minor repairs on vessels, and promptly communicate or address mechanical issues as needed.
• Provide excellent customer service by anticipating guest needs, resolving concerns professionally, and helping create a safe and memorable experience.
• Support communication and collaboration between departments to help ensure smooth daily operations and alignment with company goals.
• Promote a productive, professional, and safety-focused work environment for captains and crew.

Requirements

• Minimum of 5 years of experience as a boat captain.
• Proven experience operating and navigating vessels safely and efficiently.
• Strong knowledge of Kauaʻi ocean conditions, weather patterns, and marine safety practices.
• Knowledge of applicable regulations and laws governing vessel operations.
• Ability to work flexible hours, including weekends and holidays.
• Ability to work well under pressure and respond to emergencies with professionalism and clear communication.
• Strong leadership, communication, and interpersonal skills.
• U.S. Coast Guard Merchant Mariner Credential, 50 GRT.
• FCC Radio Operator Permit.
• TWIC Card.
• Valid driver’s license and reliable transportation.

Benefits

• Basic medical insurance, including drug and vision coverage.
• Optional dental insurance.
• Simple 401(k) plan with company match up to 4%.
• Paid time off program.
• Employee referral program.
• Employee discount program.
• Employee Assistance Program.
• Paid volunteer program.
• Continuing education reimbursement.
• Opportunities for professional development and advancement.
• Collaborative and supportive work environment.

How to Apply

Please submit your resume and cover letter outlining your relevant experience and why you would be a good fit for this position. You are also welcome to fill out an application in office.

Holoholo Charters
4353 Waialo Road, Suite 5A
Eleʻele, HI 96705

Experienced and qualified boat captains who are looking for a rewarding leadership opportunity are encouraged to apply.