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Assistant Head Instructor: Step 1 or Step 2


Step 1 is a Basic Sailing 101 course offered to children ages 8 and up in the Greater Boston Area. Each student attends Step 1 for one week. During this time, they are introduced to sailing theory and gain sailing experience in Boston Harbor.
Step 2 is a Beginner Sailing course for three weeks and at the end, if they have progressed enough, the students can get tested to move up to Step 3 is an Intermediate Sailing course offered to children ages 10 and up in the Greater Boston Area. Each student attends Step 3 for three weeks. During this time, they study sailing theory, sail Rhodes 19s.


  • Assist the Step 1 & 2 Leader in creating lesson plans for each week
  • Assist the Step 1 & 2 Leader in creating sail plans each day that you share with the site director
  • Prepare lessons for days when sailing is not possible
  • Facilitate chalk talks for students
  • Over see Step 1 & 2 instructors as they give chalk talks and instruction
  • Test students who are ready for Step 3
  • Do chores at the end of each day
  • Attend all 4 days of staff orientation
  • Attend staff meetings
  • Be a cooperative member of the Youth Program staff
  • Maintain a fun, positive, friendly atmosphere for your students
  • Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person


  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • 2-3 years sailing instruction experience
  • Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references
  • A passion for sailing, the ocean, and working with kids