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.

Available Positions

  • IIT Program Coordinator

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Beginner Head Coach

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Beginner Assistant Coach

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Advanced Head Coach

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Advanced Assistant Coach

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Intermediate Head Coach

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students Read More
  • IIT Intermediate Assistant Coach

    IIT Intermediate Head Coach DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. Read More
  • Environmental Education Program Coordinator

    Environmental Education Program CoordinatorCourageous Sailing CenterCharlestown Navy Yard, Boston, MA Reports to Youth Program Director and Youth Program Outreach Coordinator OverviewCourageous Sailing Center is seeking Read More
  • Charlestown Site Director

    ** please excuse our appearance while this site is under construction ** Charlestown Site Director Job Description [coming soon] RequirementsAttend all 3 days of staff orientationAttend staff Read More
  • Sailing School Coordinator

    Sailing School Coordinator DescriptionThe Sailing School Coordinator will be responsible for organizing the daily operations of our Step 1, 2, 3, and 4 summer sailing Read More
  • Step 1 & 2 Leader

    DescriptionStep 1 is a Basic Sailing 101 course offered to children ages 8 and up in the Greater Boston Area. Each student attends Step 1 Read More
  • Step 1 & 2 Team Leader

    DescriptionStep 1 is a Basic Sailing 101 course offered to children ages 8 and up in the Greater Boston Area. Each student attends Step 1 Read More
  • Step 3 Leader

    DescriptionStep 3 is an Intermediate Sailing course offered to children ages 10 and up in the Greater Boston Area. Each student attends Step 3 for Read More
  • Step 3 Laser Coach

    DescriptionStep 3 is an Intermediate Sailing course offered to children ages 10 and up in the Greater Boston Area. Each student attends Step 3 for Read More
  • Step 3 Rhodes Coach

    DescriptionStep 3 is an Intermediate Sailing course offered to children ages 10 and up in the Greater Boston Area. Each student attends Step 3 for Read More
  • Step 4 Leader

    DescriptionStep 4 combines racing 420's and cruising J-22's. Students are advanced sailors looking to gain experience in both racing and cruising. Each session is 3 Read More
  • Step 4 Cruising Coach

    DescriptionStep 4 combines racing 420's and cruising J-22's. Students are advanced sailors looking to gain experience in both racing and cruising. Each session is 3 Read More
  • Step 4 Racing Coach

    DescriptionStep 4 combines racing 420's and cruising J-22's. Students are advanced sailors looking to gain experience in both racing and cruising. Each session is 3 Read More
  • Summer Youth Program Sailing Instructor

    DescriptionCourageous Sailing Center operates an extensive summer program for youth ages 8-18 at three different sites throughout the Boston area. At our main site on Read More
  • Swim Sail Science Team Leader

    DescriptionSwimSailScience (SSS) is a no-cost, fun, three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being Read More
  • SwimSailScience Assistant Team Leader

    DescriptionSwimSailScience (SSS) is a no-cost, fun, three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being Read More
  • SwimScienceSail Coordinator

    DescriptionSwimSailScience (SSS) is a no-cost, fun, three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being Read More
  • SwimScienceSail Head Sailing Coach

    DescriptionSwimSailScience (SSS) is a no-cost, fun, three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being Read More
  • SwimScienceSail Science Teacher

    DescriptionSwimSailScience (SSS) is a free three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being at Read More
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Complete our online job application.

[Note: Upload your resume and cover letter directly to this application.]

Application Resources


Contact Kate Henderson, Director of Youth Programs at kate@courageoussailing.org with any questions about applying.

IIT Intermediate Head Coach

Description
At Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students in three different sailing and teaching levels: beginner, intermediate, and advanced. Other than sailing and instructor skills, our IITs also study teambuilding, career development, and environmental education.

Responsibilities
Assist the IIT Intermediate Head Coach in creating a comprehensive lesson plan for the whole summer
Assist the IIT Intermediate Head Coach in creating 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 sailing instructors as they give chalk talks and instruction
Manage sailing instructors to aid in their leadership development
Lead chores at the end of each day
Manage time efficiently to maximize student's time on the water but making sure to be back on land when required.
Attend all 4 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

Qualifications
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
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