• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond


Friday, October 9: With winds expected to build to an average of 19 knots with gusts to 32, plan for restrictions for Red and Yellow Flag skippers and the possibility that Courageous will be closed for all sailing.          Please check back before heading over!
  • Work at Courageous

    The 2015 season is just around the corner, which means there is an opportunity for you to come spend your summer working at Courageous. You'll be outside and on the water with a great staff and sailors from age 8 and up. This could be the start of your lifelong passion for teaching sailing, educating, and organizing in your community. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More
  • Environmentalism at Courageous

    Courageous is wind powered, but we do more than just use natural energy sources. For the past several years, our young sailors have been learning about marine biology and ocean cleanup from our own Environmental Educators and award-winning partners. Read More
  • Support Courageous Kids

    As 2014 draws to a close, Courageous is celebrating a successful year of teaching sailing and more to Boston kids, and looking ahead to next year. Please consider supporting Courageous in our mission to provide high-quality summer learning opportunities for the kids who need them most by making a tax-deductible donation to our Annual Appeal before December 31. Read More
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More

Instructor Trainer, IIT Program

Reports to: IIT Program Coordinator and Head Instructor Trainer
Status: Seasonal, Full-Time
Date of Last Revision: March 13, 2015

Position Summary:

At Courageous Sailing Center, we run an intensive Instructor-in-Training ("IIT") Program for a diversified group of Boston teens ages 15-17. We have 16 instructors-in-training, each with varying levels of skill in sailing, teaching, and professionalism. The primary goal of the IIT program is to prepare them to become full instructors, capable of passing the US Sailing Level 1 examiniations, within one to three summers of training. The Instructor Trainers play a critical role in facilitating this transformation. Instructor Trainers are also responsible for leading teambuilding and creating a welcoming, supportive, and positive learning environment for all of our IITs. For more description of the IIT program, take a look at the IIT Program page: http://www.courageoussailing.org/youth/iit-program


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

  • Attend all 4 days of staff orientation (Mon June 29 - Thu July 2)
  • Create a sail plan each day with the IIT Program Coordinator and/or Head Instructor Trainer that is shared with the Site Director
  • Provide individualized coaching in sailing and sailing instruction for your assigned group of IITs in accordance with IIT Program teaching objectives
  • Facilitate chalk talks and on-the-water instruction
  • Manage time efficiently to maximize student's time on the water but making sure to be back on land when required
  • Lead chores at the end of each day
  • 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:

  • 2-3 years sailing instruction experience
  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references
  • A passion for sailing, the ocean, mentoring, and working with teens
  • Prior experience working with or mentoring teens or young adults is strongly preferred

About Courageous

Courageous Sailing is a non-profit sailing center dedicated to transforming the lives of underserved populations of youth through sailing. The program has been in continuous operation since 1987 and is based in the Charlestown Navy Yard on Boston Harbor. The youth program is supported by the operation of the adult program, grants, corporate sponsorships, individual donations and fundraising events. With a fleet of Rhodes 19s (25) , J22s (9), J24s (3), J80s (2), 420s (9), Lasers (12), and a small assortment of cruising boats, Courageous is one of the largest nonprofit, keelboat-based sailing schools and community sailing programs in the northeast. In addition to youth programs, we offer adult memberships, instruction, and racing. Courageous is a fun place to work, with a large but congenial staff and an atmosphere that encourages initiative and self-direction. In 2014, Courageous Sailing employed over 100 seasonal staff members, including over 60 sailing instructors.

COURAGEOUS SAILING is an Equal Opportunity Employer.

Courageous Sailing does not discriminate in employment on the basis of race, color, religion, sex, sexual orientation, national origin, age, genetic, disability or veteran/Reserve/National Guard status.

Life as a Courageous Kid
Youth Program
My 18th birthday, this April, inspired me to do some serious thinking about what it means to be mature and how I define adulthood. At the same time that I was working through these big questions for myself, I became a member of the senior staff for the first time at Courageous. Although I ...
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Speaking my Language
Youth Program
This summer, I was a sailing instructor in Courageous' Swim Sail Science program (otherwise known as SSS). The SSS students are from various diverse backgrounds and live all over the city of Boston. With that being said, the kids represent several different ethnicities and do not always speak Englis...
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Experiencing the J/80s
Youth Program
This past spring, Courageous received a donation that allowed the purchase of two J/80s.  J/80s are 26-foot-long sloop-rigged sport boats, with a roller furling headsail and an asymmetrical spinnaker.  The intention is, assuming Courageous likes the J/80s and finds that they suit its needs...
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A Place for Growth
Youth Program
This summer, my second at Courageous, I had the opportunity to gain a greater understanding of the Youth Program as a whole. Previously while working with the Instructors in Training, I only had a narrow view of that one piece of Courageous. Returning to Courageous, I was excited to become a part of...
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How Blue Note came to Courageous
One of of my favorite stories of 2015 is the arrival of Blue Note.   A comfortable yet sprightly 30 footer in wonderful condition, Blue Note comes to us through the generosity of the family of Dr. Paul Blum, a remarkable scientist, Peace Corps volunteer, and Boston Harbor sailor.  Blue Not...
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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



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