location_onGrand Cayman Call Us keyboard_arrow_right Book Now keyboard_arrow_right Join Our Crew keyboard_arrow_right

Join Our Five Star Crew

Five Star Charters is growing! We are actively looking to expand our crew for the below position. Please send resume and cover letter to info@fivestarcharterscayman.com.


Experienced captain with a minimum of 7 years to lead and oversee crew in providing a five star, luxury experience for guests. Responsibilities include developing and implementing standard operational procedures for crew scheduling and management, boat maintenance and management and inventory management as well as continuously working to enhance the guest experience. You will serve as the primary point of contact with the owner.

Compensation is salary plus statutory benefits, plus great tips!! 


  • Computer literate
  • Experienced in overseeing and managing a crew
  • Knowledgeable on diesel engine maintenance
  • Minimum of 5 years of experience handling 40’ plus boats
  • EFR certification
  • Current insured SCUBA instructor license
  • Must have clean police record and valid drivers license.
  • Multi-lingual with experience working with luxury organizations a big plus! 
  • Self-motivated and team motivator
  • Must be organized
  • Has a vision to grow
  • An excellent communicator
  • Someone who is responsive and responsible
  • Willing to work long hours during busy season November thru May to enjoy flexible (and paid!) schedule during off-season


  • Maintains the Five Star customer service experience
  • Leads the crew and understands everyone’s role, managing daily activity of each crew member
  • Ensures the safety, well-being and maintenance of the boat
  • Assists with repairs and maintenance of boat/company vehicles
  • Is vigilant about the condition of everything on board the boat at all times, making sure all equipment on boat/in storage is functioning at all times
  • Maintains daily log bookkeeping
  • Monitors the weathers and provides forecast updates, including a hurricane plan
  • Keeps all permits up to date and is in charge of knowing when to reapply
  • Manages waivers and greets guests with entry speech/instructions
  • Monitors alcohol consumption and jet ski usage by guests
  • In charge of purchasing and inventory for the boat and storage, including alcohol
  • Communicates daily with owner via email, WhatsApp, etc.

Please send resume and cover letter to info@fivestarcharterscayman.com.

Create Your Five Star Day in the Cayman Islands