• Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More
  • Environmentally Friendly

    Courageous is wind powered, but we do more than just use natual energy sources. For the past several years, our youngsters have been learning about marine biology and ocean cleanup through award winning partner programs. 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.

Don’t eat the creatures!
By Emily Hart This week we had our first group of Step 1 students in the sailing school. As the youngest learners, we hope to keep them coming back for years and it’s important to get them excited about Boston Harbor! We had a great discussion about the animals they see in the harbor and played a W...
Continue Reading...
Step 4: Cruising learning lessons!
Youth Program
Written by Step 4 Assistant Leader, Ian Hay Today I regained my faith in adolescents’ possession of common sense. The day was intolerably muggy and boat assignments seemed dubious as I watched my students tack deep close reach to deep close reach up out of the Mystic. We had already narrowly escape...
Continue Reading...
Welcome back to Environmental Education at Courageous Sailing!
By Emily Hart, 2014 Environmental Education Program Coordinator: I’m excited for my first summer at Courageous as the Environmental Education Program Coordinator. We’ve had a great first week! We have two initiatives this summer to encourage staff and students to take positive actions on environme...
Continue Reading...
Day 4 of the Challenge
By Judith Krimski Ladies in da House! This intrepid reporter, AKA Master of the Obvious has noticed that WOAH! THE LADIES are dominating Corporate Challenge 2014. We racing sailors are all cognizant of the fact that sailing is a male dominated sport. I am reminded of this every time I go to a Lase...
Continue Reading...
June 16- Day 3 Recap
Monday, June 16. By resident Challenge Blogger Judith Krimski.  Yes, there was more of that sailboat racing stuff on Boston Harbor. Winds veering from easterly sea breeze to SW. It never fails. Just another stellar night on Boston Harbor and my "happiness quotient" is a solid 9.99999. Every t...
Continue Reading...

Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Thank you to our donors

Distrigas Logo BNY Mellon State Street Logo
alphagraphics Triumph Modular Building americorps Parks and Rec premier capers catering peterson party center gordons wine and liquor Catering Name Tag