• yp-rhodes-two-boys-on-rail
  • IIT
  • CourageousSailing05
  • two-iit-on-dock
  • 64shore
  • Summer Sailing Students
  • Rozalia Project at Courageous-21
  • IIT-program
  • ap-cruising-courses
  • yp-excited-boy-classes

Head and Assistant Instructor: Steps 1, 2, or 3

Reports to: Site Director and Youth Program Director
Status: Seasonal; full-time
Date of Last Revision: December 17, 2015


  • Step 1 is a Basic Sailing 101 course offered to children ages 8 and up. The course is four or five days long depending on the week. During this time, they are introduced to sailing theory and gain sailing experience on Boston Harbor.
  • Step 2 is a more intensive Beginner Sailing course that takes place over three weeks and provides a more in-depth introduction to sailing theory and boat handling.   
  • Step 3 is an Intermediate Sailing, three-week course offered to children ages 10 and up.  Students learn to sail more independently in Rhodes 19s without instructors in the boat.  Instructor supervision is provided from a motorboat. 


  • Manage a team of between three and six sailing instructors.
  • Create lesson plan for each session
  • Create a float 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 instructors and aid in their leadership development
  • Lead chores at the end of each day
  • Disseminate evaluation surveys weekly
  • Communicate with the parents of 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 3 days of senior staff orientation and 5 days of all-staff orientation
  • Attend staff meetings
  • Be a constructive and friendly member of the Courageous team
  • 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


  • 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

2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday 8:30 AM – 4:00 PM, from Tuesday, July 5 – Friday, August 19