Job Title: Cruising Instructor

Reports To: Adult Program Director
Status: Part-time
Date of Last Revision: June 2014

Position Summary

Courageous Sailing, a 501(c)3 nonprofit engaged in sailing education for Boston youth and the community, seeks US Sailing certified Cruising Instructors to teach courses and private lessons, May 1st through October 31st.  Most classes run on the weekends and weekday evenings.

Respond with a cover letter and resume, only via email, to:


These include, but are not necessarily limited to, the following:

  1. Teach US Sailing Basic Keelboat or Cruising according to the curriculum as laid out by US Sailing and Courageous Sailing
  2. Provide a safe, positive and fun learning environment for students
  3. Be a knowledgeable ambassador for Courageous Sailing, Charlestown, Boston Harbor and the sport of sailing
  4. Exercise good judgement in challenging situations, both on and off the water 


  1. Teaching sailing on Boston Harbor - not a bad way to spend your spare time
  2. Compensation: $15/hour for US Sailing-certified Keelboat Instructors; $20/hr for certified US Sailing-certified Cruising Instructors with USCG license
  3. Free membership for instructors who commit to teaching at least 4 full Basic Keelboat classes during the season. Check out our website for details, but this means free use of the fleet and access to all member racing, events, parties, etc.
  4. The chance to have a really good time, become a better sailor and better teacher, and be part of a great organization.


Minimum qualifications include:

  1. Captain's License or "six-pack"
  2. Current First Aid/CPR certification
  3. Passing sailing checkout with Head Cruising Coach or Sailing Director
  4. CSC motorboat qualified (mandatory in-house certification equivalent to completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course)
  5. Experience teaching sailing
  6. Positive and enthusiastic attitude
  7. Self-starter with strong work ethic and attention to detail
  8. Team-oriented
  9. Outstanding references
  10. A passion for grassroots sailing, cruising, the ocean and the environment

Other Considerations for this position 

  1. US Sailing certifications (Lifeguard, EMT, WFA, WFR, etc.)
  2. Additional teaching experience, especiallly outdoor or experiential education
  3. Previous experience cruising Massachusetts Bay and surrounding waters a plus 

About Courageous

Courageous Sailing is a non-profit sailing center dedicated to transforming the lives of underserved populations of youth through sailing. The program has been in continuous operation since 1987 and is based in the Charlestown Navy Yard on Boston Harbor. The youth program is supported by the operation of the adult program, grants, corporate sponsorships, individual donations and fundraising events. With a fleet of (25) Rhodes 19s, (9) J22s, (3) J24s, (10) 420s, (12) Lasers, and a small assortment of cruising boats, Courageous is one of the largest nonprofit, keelboat-based sailing schools and community sailing programs in the northeast. In addition to youth programs, we offer adult memberships, instruction, and racing. Courageous is a fun place to work, with a small, congenial staff and an atmosphere that encourages initiative and self-direction.

COURAGEOUS SAILING is an Equal Opportunity Employer.

Courageous Sailing does not discriminate in employment on the basis of race, color, religion, sex, sexual orientation, national origin, age, genetic, disability or veteran/Reserve/National Guard status.