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Sailing Instructor

Reports to: Head Instructor
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015


Courageous Sailing  operates an extensive summer program for youth ages 8-18 at three different sites throughout the Boston area. At our main site on Pier 4 in Charlestown Navy Yard we have a five-step program that takes students from basic classes through instructors in training (IIT) as well as a program that provides free sailing and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond and Camp Harbor View sites. Our instructors are skilled sailors who act as role models and function well as a team. Please find the descriptions of each step and other summer programs on our website, all for which we are hiring sailing instructors.


Sail in boat with students
Have students assist with sailing the boat
Teach sailing safety
Follow directions given from your step leader
Attend all 5 days of staff orientation
Attend staff meetings
Be a constructive and friendly member of the Courageous team
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


Exceptional sailing ability
Current First Aid/CPR certification
At least one year of sailing instructor experience for Step 1 and SSS
At least two years of sailing instructor experience for Steps 2 and 3
Positive and enthusiastic attitude
Outstanding communication and team management skills
Excellent references
A passion for sailing, the ocean, and working with kids

2016 Schedule:

All Staff Training: June 27-July 1
Monday-Friday 9:00 AM – 4:00 PM, from Tuesday, July 5 – Friday, August 19