• Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents. Summer vacation doesn’t need to be over.
  • Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Summer Youth Sailing Program
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    Registration is now closed. View the FAQ to learn what to do if your child was registered successfully or put on the waiting list. The FAQ also details the 2016 fees and scholarships. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

Youth Program


Courageous annually serves over 1,000 children, ages 8 to 18, out of three sailing venues in the City of Boston: Charlestown Navy Yard, Jamaica Pond, and Camp Harbor View. At our headquarters on Pier 4 in the Charlestown Navy Yard, we operate a "five-step" summertime sailing school program that takes students from "Learn-to-Sail" through "Instructor-in-Training" programs. Each Step in our curriculum includes sailing instruction, environmental education, and leadership training components. The Charlestown site also hosts two programs that provide free sailing and science programming to Boston Public School students. We operate similar though smaller-scale programs at both Jamaica Pond and Camp Harbor View.



Thank you for your application!

Please check your email Inbox (and Spambox!) for confirmation that we have received your application form. This email will contain a copy of your submitted application so that you may review it for any mistakes. Please feel free to contact us with any questions: 617-242-3821 x12 or youthprogram@courageoussailing.org.


Science Specialist

Reports to: Youth Program Director
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015


Science education is incorporated into all levels of the Summer Youth Program, ranging from practical marine biology and environmental education to basic physics and engineering. We take advantage of our location on Boston Harbor to give students direct experience with this ecosystem and to foster a lifelong sense of curiosity and stewardship. Kids also use sailing as a springboard to explore relevant science topics, like buoyancy, aerodynamics, weather, and simple machines. Our science classes are hands-on, interactive, outdoors, tied to what kids are doing and learning every day, and--most importantly--fun. This job is a fantastic opportunity for a certified teacher who wants to share his/her passion for science without the schedule and testing constraints of a classroom.

The Science Specialist will develop and teach a variety of lessons. Afternoons will be devoted to working with the rising 4th and 5th grade participants in Swim Sail Science, an outreach program that combines English Language Arts and Math (taught by Boston Public School teachers) with swimming, sailing, and science. The Science Specialist will collaborate with the BPS site coordinator and teachers to build a curriculum that will complement the ELA content on simple machines; additional lessons will focus on the marine life of Boston Harbor. Swim Sail Science students will also meet with the Science Specialist for team building activities each morning.

The Science Specialist will also teach one lesson per week to the 8-9 year olds in our one-week introductory sailing class, in which students will learn about the creatures in Couragous’s on-site lobster trap and their role in the harbor ecosystem. In collaboration with Courageous’s Education Director, the Science Specialist will likely create, prepare, and teach up to 3 middle school level lessons (for more advanced sailors) on sailing-related physics, engineering, or weather topics. Additionally, the Science Specialist is responsible for organizing activities and awareness campaigns to promote environmental stewardship, recycling, and resource conservation.


  • Develop and teach science curricula to sailing students (aged 8-14) and Swim Sail Science outreach program participants (rising 4th and 5th graders).
  • Before program, become familiar with the BPS summer ELA curriculum and create related lessons (in consultation with the BPS site coordinator and the Education Director).
  • Promote environmentally friendly culture at Courageous, including publicizing and encouraging Waste-Free Wednesdays, recycling, fresh water conservation, and more
  • Promote awareness and stewardship of the Boston Harbor ecosystem by posting “fun facts” about marine life, challenging students and instructors to look for various species, and serving as a resource for sailing instructors.
  • Lead morning team building and journaling activities with Swim Sail Science students.
  • Help colleagues with other Swim Sail Science duties when possible.
  • Must attend staff orientation and all 6 weeks of summer program, dress in Courageous uniform, and provide own transportation to Courageous Sailing.


  • MA teaching license
  • Passion for science, the ocean, nature, and working with kids
  • Minimum 2 years leading hands-on environmental/science activities or teaching classroom science
  • Experience with curriculum development
  • Familiarity with New England flora, fauna, and sea life
  • Ability to handle sea life responsibly
  • Willingness to teach outside in potentially challenging conditions (noisy, rainy, hot) with minimal materials
  • Strong communication and teamwork skills
  • CPR and First Aid Certifications
  • Ability to lift 30 lbs.
  • Note: ability to sail is not necessary**

2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday 8:00 AM – 3:00 PM, from Tuesday, July 5 – Friday, August 19


Site Director and Assistant Site Director

Reports to: Youth Program Director
Status: Seasonal, Full-Time
Date of Last Revision: May 2016
Please note that while the Site Director position has been filled, we are still accepting applications for the Assistant Site Director position.


Courageous Sailing operates summertime youth sailing programs at three different locations: the Charlestown Navy Yard on Boston Harbor; Camp Harbor View, located on Long Island in Boston Harbor; and Jamaica Pond, a smaller, freshwater venue located in the heart of the city of Boston.  
At each site, a Site Director and Assistant Site Director are responsible for overseeing the day-to-day operation of the youth programs at that site. The Site Directors report to the Youth Program Director, and supervise Head Instructors (5-7 at Charlestown; 2-3 at Jamaica Pond; 2-3 at Camp Harbor View).

Each Site Director functions like their site's principal and operations manager. This position is a great leadership opportunity for the sort of individual who, for example, has previously been a Head Instructor at another program and is interested in gaining more staff/logistics management experience.


  • Training and Communication
    • Collaborating with the Youth Program Director and Youth Program Outreach Coordinator to plan and conduct Staff Orientation, Staff Development Clinics, and weekly staff meetings
    • Attending all Senior Staff meetings
    • Communicating daily events, needs, issues and successes to the Head Instructors, Youth Program Director, Youth Program Outreach Coordinator, Evaluation Coordinator, Fleet Manager, and Adult Program Director, as needed or as appropriate
  • Site Management
    • Opening and Closing the site each day (8 am - 4 pm)
    • Managing the division of site resources between Head Instructors and their respective classes
    • Communicating via radio with all Head Instructors to coordinate the safe departure and return of each class at the beginning of the day, lunchtime, the end of the day, and during any emergency management procedure (e.g. bringing boats home before incoming weather event)
    • Communicating via radio with passing ships, ferries, barges and others for whom the youth sailing program may pose a navigational obstruction or hazard
    • Ensuring all boats are tied down and equipment is stowed properly at close of each program session
    • Ensuring the facility is clean and ready for the next day or programs beginning after 4 pm
  • Staff and Student Management
    • Promoting a culture of safety, fun, and learning
    • Work with the Youth Program Director and Outreach Coordinator to create a strong sense of community and support among the staff members at your site
    • Working  to track students' attendance
    • Working to ensure all staff time cards are complete and accurate
    • Ensuring all youth programming proceeds on time
    • Approving Head Instructors' Daily Float and Lesson Plans, and, as needed, discussing ways to execute their plans more effectively or safely
    • Resolving any issues with students, parents, and staff members, as well as passing these on to the Youth Program Director if problems persist
    • Enforcing all safety and instructional standards, and leading the Emergency Action Plan
    • Maintaining an injury log and ensuring all incident reports are completed and delivered to the Youth Program Director in a timely fashion
    • Interim and end-of-season evaluations of Head Instructors and any other supervisees
  • Performing additional related tasks as designated by the Youth Program Director
  • * Please note that specific duties, schedule, responsibilities vary slightly by site, and listing each difference here would be inefficient.  The Charlestown site, which puts over 100 youth and instructors on the water daily, is far larger than either the Jamaica Pond or Camp Harbor View sites.  Site Directors in these locations function more like traditional Head Instructors. Clarification and more details will be discussed during the candidate's interview.


  • Experience leading teams of staff members within youth development, sailing, education, or camp settings
  • Experience making weather-related programming decisions utilizing a combination of online tools, sensory cues, past experience, and sound judgement
  • Comfort with VHF radio communication
  • Ample experience in sailing and sailing instruction
  • Current First Aid and CPR certification, or more advanced, is required
  • A love for mentoring younger staff and for creating a sense of community and camaraderie among co-workers
  • Current US Sailing Small Boat Level 1 Certification or its equivalent is preferred but not essential
  • Competency in driving a range of small outboard powerboats (e.g. center-console, 17' Boston Whalers and Easterns)

2016 Schedule:

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

IIT Program Coordinator/Head Trainer

Reports to: Site Director
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015


At Courageous Sailing, we run an intensive Instructor-in-Training (IIT) Program for a diversified group of Boston teens ages 15-17. We have up to 22 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 examinations, 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.


  • Work with IIT Asst. Trainers to create a comprehensive lesson plan for the whole summer
  • Work with IIT Asst. Trainers to create a float plan each day that is shared with the site director
  • Make sure all students and staff adhere to the designated schedule
  • Prepare lessons for days when sailing is not possible
  • Facilitate chalk talks for IITs
  • Oversee IITs as they give chalk talks and instruction
  • Manage IIT Asst. Trainers and IITs and aid in their leadership development
  • Lead chores at the end of each day
  • Manage time efficiently to maximize students' time on the water 
  • Organize and chaperone camping trips, BBQs, race nights, and other fun events for the IITs throughout the summer
  • Complete MWBLP for all IITs and staff
  • Distribute evaluation surveys
  • Attend 3-day senior staff orientation and all 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


  • Bachelor's degree or currently in school for High School education or outdoor education
  • 3-5 years experience teaching teens
  • 2-3 years team management experience
  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • 2-3 years of sailing instruction experience
  • Courageous Sailing motorboat qualified (mandatory in-house certification equivalent to completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level 1 certification course)
  • Passion for working with urban teens
  • Commitment to creating a positive IIT team
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references


2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday, from Tuesday, July 5 – Friday, August 19


Learning the Ropes
Youth Program
I had a great summer at Courageous Sailing and have had a number of memorable experiences with kids on the water. One that stands out most to me happened with a student in Step 2. This student was always his own person and has a very colorful disposition but, because of this, had trouble showin...
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Mi Barco es Su Barco
Youth Program
The Swim Sail Science! program at Courageous this summer was very different than the summer youth programs that we have always had. Half of the students' summers were spent in math and reading classes, where they learned about different water systems and our limited supply of fresh water i...
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Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129



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