First Mate, Sailing Vessel (Caribbean)

Year-round | $4,000/month + room and board | Trinidad to St. Maarten

Do you want to use your license to do work that matters? Whatever It Takes Expeditions is hiring a First Mate for our 100' school ship, where high school students sail the Windward and Leeward Islands on a rite of passage expedition.

This is a hands-on role. You will keep the vessel running, and you will teach, coach, and mentor students every day. You will lead shore activities, supervise students, teach coursework, and manage student apprentices, alongside your duties as a mate.

The Vessel

• 100' Giorgetti & Magrini ketch-rigged sailing yacht

• Accommodations for 12 students and 6 staff

• Staff cabins are separate from student quarters, with shared cabins and a shared bathroom

The Schedule

• Year-round position

• Students are aboard 30 to 35 weeks per year

• During expeditions: 7-day work week, with days off in port when available

• Between expeditions: standard 5-day work week, with the First Mate keeping the vessel manned (typically at anchor)

• The vessel may be chartered during off weeks

• No operations over the Christmas holidays

• 20 days PTO

Reporting

You report to the Fleet Manager and work day-to-day with rotational Captains.

Responsibilities

• Perform daily, weekly, monthly, and annual maintenance on all systems

• Lead the Engineering Department

• Diagnose and repair systems as needed

• Stand watch and support the Captain in safe navigation and vessel operation

• Follow and uphold program Standard Operating Procedures at all times

• Build strong bonds with each student through 1:1 and group time

• Build teamwork among students and staff

• Teach coursework and manage student apprentices

• Lead shore-side activities and supervise students

• Join service learning projects and all youth programming

• Other duties as assigned

Minimum Qualifications

• Commercial Master or Mate license accepted by the vessel's flag. Examples of qualifying licenses:

  • USCG 50-Ton Master or higher

  • RYA Yachtmaster Offshore (commercially endorsed) or higher

  • IYT Master of Yachts 200 or higher

  • MCA Officer of the Watch (Yachts <500GT) or higher

  • Equivalent national or flag-state commercial license

• 2+ years as Captain, Master, or Mate of a sailing vessel

• STCW Basic Safety Training

• Current First Aid and CPR (STCW Elementary First Aid or equivalent)

• Lifeguard certification (RLSS, Red Cross, or equivalent)

• Valid seafarer medical certificate (ENG1, ML5, or equivalent)

• Valid passport

• Working knowledge of yacht systems, with the ability to learn the rest fast

• Empathy for the life experiences of the youth Whatever It Takes Expeditions serves

• A real passion for mentoring and coaching

Not sure if your license qualifies? Apply anyway and tell us what you hold. We will confirm whether it is accepted for the vessel.

Compensation and Benefits

• $4,000 per month

• Room and board

• 20 days PTO (accrues, usable after 90 days)

• $1,500 flight budget for PTO travel (home port or vacation destination)

• Additional pay for private charters

• International health insurance

• Work cell phone with international plan