• 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
  • 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

Job Title: Fleet and Facilities Manager

Reports To: Executive Director
FLSA Status: Non-exempt
Status: Full-time
Date of Last Revision: September 2013

Position Summary

Courageous Sailing, a 501(c)3 nonprofit engaged in sailing education for Boston youth and the community, seeks a Small Boat Technician and Fleet and Facilities Manager to maintain our fleet. Reporting to the Executive Director, the Fleet and Facilities Manger will plan and oversee all operational and budgetary functions related to the maintenance of Courageous Sailing’s fleet and facilities.

Candidates should be sailors with experience in all aspects of boat repair and maintenance, including fiberglass work, carpentry, rigging, and painting. Enthusiasm and willingness to learn are essential, and we can train the right person in the specific skills that are needed. There is opportunity to advance from Small Boat Technician to Fleet and Facilities Manager in a short amount of time.

This is a full-time, year-round position with peak workload in the fall and spring months. Compensation range according to skill and experience: Small Boat Technician, $13-15/hour; Fleet Manager, $15-20/hour plus benefits.

Respond with a cover letter and resume, only via email, to:  dave@courageoussailing.org.



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

  1. Oversee and perform dock, fleet, and building maintenance in compliance with applicable laws and regulations.
  2. Hire and supervise maintenance staff
  3. Maintain a comprehensive maintenance log. 
  4. Perform annual condition survey for major equipment and fleet.
  5. Develop and manage the budget for Courageous maintenance programs.
  6. Coordinate all maintenance calendars and personnel schedules with Program Directors to complement program needs.
  7. Participate in operational planning for Courageous Sailing as a whole.
  8. Take primary responsibility for maintenance procurement with outside contractors and vendors in compliance with applicable laws and regulations
  9. In coordination with Program Directors, take responsibility for safe and prudent practices with respect to the fleet and facilities.


The Fleet and Facilities Manager position is a year round hourly position requiring a high level of proficiency in boat mechanics, maintenance and repair practices. 

Minimum qualifications include:

  1. Excellent communication skills
  2. Bachelor’s degree or equivalent technical certification
  3. Excellent interpersonal skills and a commitment to promotion of high quality sailing experiences, particularly for underserved populations.
  4. Demonstrable sailing abilities
  5. Motorboat certification
  6. Minimum of two years’ experience in small  boat and routine outboard motor maintenance

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.

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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



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