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Position: Lead Deckhand

Company: Thompson Island Outward Bound Education Center

Location: Thompson Island, Boston, MA

Lead Deck Hand reports to Maritime Manager (Boat captain while vessel in use)


As Soon As Possible


Full Time, Year Round, Non-Exempt


The Lead Deck Hand Position is for the individual looking to make a career in the maritime field and is seeking to build a skill set which reflects that. The goal of this position is to build a strong confident mariner in all aspects of the industry through a wide variety of projects both on and off the vessel. In conjunction with the captain, the Lead Deck Hand is responsible for the safe operation of a 65’ passenger ferry in daily runs to and from Thompson Island, and around the Boston Harbor. This position reports directly to the Captain on Duty while the vessel is in use.


  • Throw/Handle mooring lines, assist with vessel cargo, and communicate safety concerns to passengers
  • Routine Engine Maintenance (Will Train)
  • Maintain Accurate Log Books (Will Train)
  • Train All New Seasonal Deckhands
  • Maintain a safe and clean vessel for passengers
  • Keep Captain informed of safety concerns while vessel is running
  • Assist in general vessel, dock and equipment maintenance
  • Additional responsibilities as assigned by the Maritime Manager.


In conjunction with the captain, the Lead Deck Hand is responsible for training all new seasonal deck hands and keeping neat and accurate Engine Log Books.


  • High School Diploma desired but not required.
  • Prior maritime experience required.
  • Prior experience operating small boats desired but is not required.
  • Task and Time Management skill.
  • Comfortable interacting with students and clients from a diverse background.
  • Desire to learn all the skills necessary to thrive in the Maritime field and acquire sea time.
  • Desire to contribute, by way of fulfilling job duties, to the organizational mission of providing character development for Boston’s young people.
  • Professional presentation and demeanor, to include clean appearance (uniforms supplied) and professional communication with supervisor, peers and clients.
  • Pre-Employment DOT Drug Test (Provided).


  • Must be comfortable working outside, on the water, in all weather conditions
  • Overtime Hours Expected
  • Regular Evening and Weekend Work Required


  • Must be able lift 70 lbs unassisted.
  • Must be able to go up and down ladders carrying 30 lbs
  • Must be able ride a ferry daily and traverse an island of varying terrains.
  • Must be capable of standing for 5+ hours per day.
  • Ability to pass a drug screening test.


Competitive salary, commensurate with experience. Employer sponsored health insurance with the option to select between three comprehensive plans, Premier dental plan, vision, commuter benefits and 401(k) retirement plan with competitive match. Paid time off (PTO). Work that engages a diverse and dynamic community of educators and other professionals with the shared vision of shaping a better future for Boston’s youth.


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