Summer Jobs @Courageous

We seek highly motivated, skilled sailing instructors and educators, those who will ensure that our students are safe, have fun, and have the optimal setting to grow and learn as blossoming sailors.

Each year, Courageous hires over 100 seasonal staff and instructors. Our instruction team is enthusiastic, energetic, and diverse, united by common passions for sailing, the ocean, and working with kids. They range in age and experience from high school and college sailors, to NOLS instructors, to tall ship crew and seasoned cruisers. We also hire experienced educators, naturalists, and outdoor educators who enhance our summer programs with their unique expertise.

Our staff members also enjoy a wide range of benefts, including: racing opportunities, professional development support, connection to the growing Courageous alumni network, and the satisfaction of having a job that makes a difference. Come spend your summer sharing your passion, making a difference, and being part of an exceptional team of instructors who are united by their dedication to the Courageous mission.

Click here for information on our Instructor-in-Training Program.

  • IIT-program
  • yp-teaching-learning-sailing
  • CourageousSailing05
  • yp-smiling-kids
  • ap-cruising-courses
  • HS-sailing02
  • Staff 007
  • Courage3
  • Get ready for the ultimate adventure!
  • CitSch2-a

Complete our 2015 online job application form.

[Upload resume & cover letter to this form.]

Application Resources

Contact Kate Henderson, Director of Youth Programs at with any questions about applying.
Reports to: Site Director and Youth Program Director
Works closely with: Education Director and other Head Instructors/Coaches
Supervises: Assistant Head Instructors, Sailing Instructors, and (occasionally) Instructors-in-Training
Status: Seasonal (mid-June through mid August, exact dates TBD); full-time (between 35 and 40 hours per week, Mon - Fri)
Date of Last Revision: December 15, 2014

Program Descriptions

  • Step 1 is a Basic Sailing 101 course offered to children ages 8 and up from all over the Greater Boston Area. The course is four days long. During this time, they are introduced to sailing theory and gain sailing experience in Boston Harbor.
  • Step 2 is a Beginner Sailing course for three weeks and at the end, if they have progressed enough, the students can get tested to move up to Step 3.
  • Step 3 is an Intermediate Sailing course offered to children ages 10 and up in the Greater Boston Area. Each student attends Step 3 for three weeks. During this time, they study sailing theory, sail Rhodes 19s.


The Head Instructors of Step 1, Step 2, Step 3 manages a team of between three and six sailing instructors. 

Primary Responsibilities

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

  • Create lesson plan for each session
  • Create a sail plan each day that you share with the site director
  • Prepare lessons for days when sailing is not possible
  • Facilitate chalk talks for students
  • Over see Step 1 / 2 / 3 instructors as they give chalk talks and instruction
  • Manage Step 1 /2 / 3 assistant head instructors and aid in their leadership development
  • Lead chores at the end of each day
  • Disseminate evaluation surveys weekly
  • Communicate with the parent's of your sailing students regarding what students need to bring each day and how each student progressed
  • Manage time efficiently to maximize student's time on the water but making sure to be back on land when required.
  • Complete a Massachusetts Work Based Learning Plan for each of your instructors
  • Attend all 5 days of staff orientation
  • Attend staff meetings
  • Be a cooperative member of the Youth Program staff
  • Maintain a fun, positive, friendly atmosphere for your students
  • Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person


Minimum qualifications include:

  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • 2-3 years sailing instruction experience
  • Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
  • Outstanding communication and teaching skills
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references
  • A passion for sailing, the ocean, and working with kids