Adult Program Sailing Instructor

In by Caitlyn Ridgely

Website Courageous Sailing

Reports To: Adult Program Director and/or Site Manager

Status: Part-Time Seasonal

Description Last Updated: 1/31/2024

Courageous Sailing

Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy the waterfront. We work at two locations in Boston: the Charlestown Navy Yard on Boston Harbor, and the Historic Jamaica Pond boathouse in Jamaica Plain. Our mission is to transform lives through sailing programs that inspire learning, personal growth, and leadership.

Why Courageous? 

Working at Courageous is an opportunity to join a close-knit and diverse community committed to fostering a positive educational environment for staff and participants on and off the water.

Courageous Staff receive paid training and professional development as well as recreational access to our fleet of boats which range from dinghies to mid-size keelboats and cruising boats. 

By joining our team you will make a meaningful and positive impact on the lives of our participants and will be a critical part of fulfilling our mission to get people from all walks of life out on the water. 

Dates/Time: Part-time and Full-time shifts are available seasonally. Schedules can be tailored to individual availability; Mon-Sun, May 1st-Oct 31st.

Position Overview

Courageous Sailing is seeking instructors to teach courses and private lessons at our Charlestown and Jamaica Pond sites. Most classes run on the weekends and weekday evenings.


Participate in and contribute to a safe, engaging, and respectful work environment by:

  • General:
    • Be proactive
    • Provide clear, effective, and timely communication with leadership staff
    • Leave Courageous better than you found it
    • Teach private lessons
    • Teach Learn-to-Sail courses
  • Safety (minimizing risks while maintaining an approachable and engaging environment for students, members, patrons, and fellow staff members):
    • Responsibly manage risk so that students, members, and patrons feel comfortable stepping outside of their comfort zones, asking questions, and engaging with the facility on various levels. 
    • Comply with and encourage students and members to learn Courageous’ set of sailing safety standards and reiterate their importance whenever possible. 
    • Attend all days of staff training and staff meetings and/or complete online training.*
    • Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards.
    • Remain up to date on what roles and responsibilities you may take on in the event of an emergency and review the EAP with your direct supervisor. 
  • Respectability (support and ensure that everyone can be successful):
    • Maintain the Courageous fleet and facilities by completing everyday tasks as discussed in training and documented in daily checklists
    • Reduce and help manage the disposal of waste in and around Boston Harbor
    • Cultivate a kind and inclusive community
  • Engagement (maintaining the expectation of individual responsibility for students and members):
    • Build rapport with students, members, and patrons
    • Provide active and engaged feedback to daily questions and interactions
    • Lead, facilitate, and participate in on-land responsibilities for general upkeep of the boathouse during downtime. 

*Job training days are position dependent and vary from position to position. 

  • US Sailing Level 1 or Keelboat Instructor Certification, equivalent or more advanced preferred
    • All qualified applicants are encouraged to apply regardless of US Sailing certifications
    • Courageous is open to discussion about financial assistance in pursuing certifications
  • A passion for sailing, the ocean, and working with students
  • Can work effectively with a wide variety of age groups and populations from diverse backgrounds, role modeling inclusive behavior and building positive group culture
  • Able to communicate clearly and directly
  • Comfortable giving and receiving feedback
  • Able to build rapport easily with students and colleagues
  • Passionate about and dedicated to experiential education for students of all ages
  • Able to meet different learning style needs by varying teaching techniques
  • Sufficiently physically fit to participate in all site and course activities while maintaining ample energy, strength, and focus to aid students
  • Comfortable working outdoors, regardless of weather
  • Able to practice proper self-care and energy management 
  • Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress
  • Positive and enthusiastic attitude
  • Excellent references
  • Willing to authorize a federal background check
  • Hold, or be willing to obtain before start date, current First Aid and CPR certification

The pay range for this position is $18-25 depending on experience and relevant certifications.

To apply for this job please visit