Sailing Instructor - Courageous Sailing


Job Description

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 (IITs) as well as a program that provides free sailing, swimming and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond and Camp Harbor View sites which offer beginner level sailing opportunities. Our instructors are skilled sailors who act as role models and function well as a team. We teach on a variety of boats including Rhodes 19s, RS Quests, 420s, and Lasers. Please find the descriptions of each step and other summer programs on our website, all for which we are hiring sailing instructors.

Apply by: May 21 2017


Camp/Organization: Courageous Sailing

Location: Boston, MA

Type of Position: Specialized Activity Leader

Time Frame: Seasonal


2017 Mandatory Dates

  • All Staff Training: June 26-30 Monday-Friday 8AM – 4PM, from Monday, July 3 – Friday, August 11 (approximately 30 hours per week)
  • Staff Retrain Day: Monday, July 24 
  • End of Season Staff Day: Monday, August 14 
  • Additional work is available Tuesday, August 15 – Friday, August 25 

All staff are eligible to request up to 3 vacation days



  • Exceptional sailing ability
  • Current First Aid/CPR certification 
  • Experience as a sailing instructor preferred 
  • Positive and enthusiastic attitude 
  • Outstanding communication and team management skills 
  • Excellent references 
  • A passion for sailing, the ocean, and working with kids

Additional Information

For more information visit:


Apply Here


Toni Sacco

<p>One First Avenue <br />Boston, Massachusetts 02129</p>