• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Summer Youth Sailing Program
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    Registration is now closed. View the FAQ to learn what to do if your child was registered successfully or put on the waiting list. The FAQ also details the 2016 fees and scholarships. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

Spring After School Sailing Instructor / Head Instructor

Status: Seasonal, Part Time
Date of Last Revision: January 27, 2016


Courageous runs a variety of spring after school programs for neighborhood elementary and high school students. We offer two 4-week beginner/intermediate spring programs from late May through mid June. One program, called Charlestown After School Sailing, is geared towards 3rd-6th graders, many of whom also participate in our summer program. Another program serves local high school students, primarily youth from underserved populations, who are absolutely new to sailing and want to try it out. We’re also looking for instructors for our pilot Work-Sail program for at-risk teens interested in learning how to sail, building professional and teaching skills, helping around the boathouse, and eventually becoming summer program instructors-in-training. This program runs April 26-June 10. Courageous is looking for instructors to sail on Rhodes 19s with 3 kids at a time, teaching beginner/intermediate sailing and participating in group activities. We are also hiring a head instructor for the two 4-week programs. 


Instructor responsibilities vary slightly depending upon the program and position, and include some or all of the following:


  • Sail a Rhodes 19 with up to 3 students
  • Individualize sailing instruction to each student’s level, needs, and learning style.
  • Help plan activities; teach independently and participate in group activities and drills led from a motorboat.
  • Ensure a safe, fun, inclusive, supportive environment.
  • Walk elementary-aged participants to and from school.

In addition, the head instructor will:

  • Plan curriculum and lead daily activities in collaboration with instructors.
  • Supervise sailboats and lead activities from a motorboat.
  • Keep records of attendance, daily boat assignments and activities, incidents/injuries, etc.
  • Coordinate instructor schedules.


  • 2+ years sailing experience; solid sailing skills
  • 1+ years teaching sailing to youth or participating in an Instructor Training or Junior Instructor program
  • Positive, enthusiastic, and flexible attitude
  • Strong problem solving skills and an ability to adapt to changing program needs depending on changes in weather, number of students, number of boats, etc.
  • A passion for sailing, the ocean, the environment, and working with kids
  • Head Instructor must have US Sailing Level 1 certification and be able to operate a motorboat and tow sailboats competently


Other considerations for this position ("nice-to-haves," not requirements):

  • Other certifications (Lifeguard, EMT, WFA, WFR, etc.)
  • Prior experience working with children in a school, after school, or camp setting
  • US Sailing Small Boat Level 1 Instructor Certification (or equivalent) helpful, but not required at this level
Learning the Ropes
Youth Program
I had a great summer at Courageous Sailing and have had a number of memorable experiences with kids on the water. One that stands out most to me happened with a student in Step 2. This student was always his own person and has a very colorful disposition but, because of this, had trouble showin...
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Mi Barco es Su Barco
Youth Program
The Swim Sail Science! program at Courageous this summer was very different than the summer youth programs that we have always had. Half of the students' summers were spent in math and reading classes, where they learned about different water systems and our limited supply of fresh water i...
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Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129



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