Employment Opportunities at Courageous

Adult Program Employment
At Courageous we are committed to making the highest quality sailing education accessible to the community. We rely on instructors who are both great sailors and great teachers. If you have taught sailing before, or have wanted to, we want to hear from you!

Adult Program Instructor positions are typically part-time, with most classes running on the weekends and weekday evenings, so are often a great fit for those with "real jobs" who want to do something totally different in their spare time.  Some full time instructor positions are also available.

Laser Coaches
Are you an experienced Laser coach?  We just added a fleet of 12 brand-new Lasers to our fleet, and are looking for the right coach or coaches to manage the fleet, run clinics and regattas for both the youth and adult programs.

Keelboat Instructors
We are currently seeking experienced keelboat, cruising, navigation and racing instructors to join our instructor team for the 2011 season, which runs from April 30 to October 31. Most adult program classes run on the weekends and weekday evenings.

Applicants must...
  • Be experienced, confident sailors AND great teachers
  • Be available to work some weekends or weekday evenings
  • Support high quality community sailing
  • Be willing to continue to learn and participate in in-house instructor training
  • Have current CPR/First Aid certifications

Current US Sailing Keelboat/Cruising Instructor certification is preferred. For those that don't have their certification yet, we are hosting a three-day US Sailing Keelboat Instructor class, April 15-17, 2011.


Teaching sailing on Boston Harbor - not a bad way to spend your spare time

Compensation: $15/hour for US Sailing-certified Keelboat Instructors; $20/hr for certified US Sailing-certified Cruising Instructors with USCG license

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.

The chance to have a really good time, become a better sailor and better teacher, and be part of a great organization


To Apply for Instructor Positions
For all adult program instructor positions, please send resume and cover letter, or questions, to dave@courageoussailing.org

Courageous Sailing Staff

Running a sailing center is a group effort! If you love working around boats and people and want to join our staff, I want to hear from you! We have many seasonal (May 1 through October 31) positions available helping members around the boathouse, on the dock and on the water. We will train, but some sailing experience is required.

Come work at a great sailing center, with great people, helping us make sailing accessible to the community.


To Apply for Staff Positions

Please complete our online application form. Apply today!

Youth Program Employment

In the Courageous youth program, we strive to transform kids' lives through the sport of sailing. Our sailing school's instruction team works not only to foster students' love of sailing, adventure and the outdoors, but also to give them the values, skills and confidence that they will need to thrive in their lives beyond Courageous.

The Courageous Youth Programs have opportunities for everyone from aspiring instructors to seasoned outdoor educators and youth program managers. Job descriptions for the 2012 season have now been posted (click on the list of links below).

Give back. Change Lives. Apply today!

To Apply:

(1) Compose a cover letter that lists the positions you are interested in, describes your qualifications for these positions and explains why you wish to work at Courageous Sailing.

(2)  Update your resume, in a way that highlights any relevant experience in sailing instruction, sailing, teaching, coaching, working with youth, etc. Please also list and/or send photocopies of any relevant certifications.

(4) In the event that the application form is not working for you, you may also email or mail all of the above application materials to the Director of Youth Programs:



Attn: Kate Henderson
Director of Youth Programs
Courageous Sailing
One First Avenue
Charlestown Navy Yard
Boston, MA 02129


*** 01/03/12: Apologies as links to specific job descriptions are not yet live. They will be soon. Unless a position is explicitly listed as "filled," assume that the position is open for 2012. Thank you for your patience! ***


  • Camp Harbor View Site Director (position filled)
  • Charlestown Asst Site Director (position filled)
  • Laser Lead Instructor/Coach
  • Instructor In Training Program Head Coach
  • Instructor in Training Program Asst. Coach
  • Assistant Laser Instructor/Coach



There are no available positions in this department at this time.  Thank you for your interest!

Getting Started

Never been sailing? Get ready for the ultimate adventure! In just one lesson you'll be out on the water. If you like it—which we're sure you will—before long you'll be skippering a boat, racing on a team, or cruising around the harbor islands. If you stick with it, one day you could even be a Courageous instructor!  While you're on the water, you're going to learn lots about the environment and get to practice some pretty important life skills, too. From fishing off our pier to overnight island camping trips, you'll be having fun on adventure after adventure, all year long!

Read the website and still have questions? Email your questions to Ashton Smith at ashton@courageoussailing.org or call 617-242-3821.



Courageous Mainsail Partners


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