• Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents. Summer vacation doesn’t need to be over.
  • 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


Sunday, Oct. 23nd: CLOSED FOR THE DAY, due to a gale warning and gusts up to 35 knots through this evening.
  • 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

High School Sailing Coach

Status: Seasonal, Part-Time
Date of Last Revision: January 26th, 2016


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.


  • With fellow coaches, plan and carry out a curriculum that will build boat handling, racing, and (for the racing team) rules knowledge and team racing skills.
  • Lead team building activities; maintain a positive, supportive, fun, and sportsmanlike environment.
  • Supervise safe and effective team practices from a motorboat; provide constructive feedback to sailors.
  • Keep records of attendance, daily boat assignments and activities, incidents/injuries, etc.
  • Ensure that sailors are taking care of team equipment (drysuits, helmets, etc.) and boats; promptly report any maintenance issues. Prep and put away motorboats.
  • Work with Education Director to collect required paperwork from students, follow school policies, and communicate with the coaches of other teams about scheduling races.
  • Lead interactive chalk talks; be prepared with indoor activities (rules quizzes, videos, etc.) in case of bad weather.
  • Run team races plus up to 3 fleet regattas; hear protests as necessary.
  • Travel to up to 4 local championships.


Job Requirements:

  • Excellent dinghy and keelboat sailing and racing skills. Racing coaches must be experienced team racers.
  • 1+ years experience as sailing instructor and/or racing coach
  • Current First Aid/CPR certification
  • US Sailing Level 1 certification; equivalent experience considered
  • Flexibility, problem solving skills, organization, and the ability to work with a coaching team
  • Extensive experience operating a motorboat and righting capsized dinghies
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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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



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