• 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
  • Support Courageous Kids

    As 2015 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
  • 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
  • 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

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.


Environmental Education Program Coordinator

Reports to: Youth Program Director and Youth Program Outreach Coordinator


Courageous Sailing Center is seeking a creative, engaging Environmental Education Program Coordinator capable of continuing our current EE program that integrates applied science learning with our Summer Youth Program sailing lessons. During our summer youth program we serve approximately 1,000 students, many of whom are here on scholarships and would ordinarily not have access to this caliber of summer programming. We have beginner, intermediate, advanced, racing, cruising, Instructor in Training sailing levels as well as two academic-focused science and sailing programs that target students who are at risk for summer learning loss.

The environmental education program incorporates practical marine biology, environmental, and outdoor education activities into all of the sailing levels of the Summer Youth Program. We take advantage of our location on Boston Harbor to give students direct experience with this ecosystem. In addition, we foster a community of environmental awareness at Courageous by encouraging recycling, trash reduction, general stewardship and environmental responsibility.

Many of the students that attend the Summer Youth Program do not have other opportunities to spend times outdoors or experience nature up-close. Therefore, it is crucial that we introduce environmental education carefully and encourage life-long learning, memorable experiences, and positive interactions with the ocean.


  • Work with the Youth Program Outreach Coordinator (previous EE Coordinator) to amend the current "Courageously Green" curriculum
  • Design a comprehensive evaluation of the environmental education program
  • Introduce EE program to staff at orientation
  • Facilitate daily EE activities for each sailing level (ages 8-17), based on a designated schedule
  • Facilitate EE activities on days/at times when sailing is not possible (too hot, too windy, raining, etc.)
  • Weekly posts on the Courageously Green Blog and encourage other staff to write for the blog as well
  • Post daily marine bio facts relevant to each week's theme
  • Promote environmentally friendly culture at Courageous; including, but not limited to, encouraging Waste Free Wednesdays, weekly pier clean-ups, composting, recycling, fresh water conservation
  • Must attend staff orientation and all 7 weeks of summer program, dress in Courageous uniform, and provide own transportation to Courageous Sailing Center


  • Passion for the ocean, nature, sailing, and working with students
  • Working towards or Bachelors degree in Environmental Studies, Science Education, Marine Biology or similar field
  • Minimum 3 years leading hands-on environmental/science activities
  • Minimum 2 years of education experience
  • CPR and First Aid Certifications
  • Experience with curriculum development and program evaluation
  • Ability to lift 30 lbs.
  • Extensive knowledge of New England floral, fauna, and sea life
  • Ability to responsibly handle sea life
  • Strong communication and teamwork skills
  • Ability to teach outside in difficult conditions (noisy, rainy, hot) with few materials
  • Note: ability to sail is not necessary**

June 22 - August 14, 2015

Monday - Friday, 8am - 4pm


Assistant Site Director, Charlestown Site

Are you a former Sailing Program Head Instructor looking for new challenges and more responsibility? Are you interested building your skills so that one day you could be leading a sailing school, leading a youth development program, or becoming a school or camp director?  Working as a Courageous Sailing Summer Youth Program Assistant Site Director could be the perfect opportunity for you! 
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 Charlestown, the Assistant Site Director works with the Site Director to oversee the day-to-day operation of the youth programs at that site. The Site Director and Assistant Site Director together report to the Youth Program Director, and supervise up to seven different Head Instructors, who each manage teams of between three and eight sailing instructors and daily classes of between 15 and 20 students. 

The Assistant Site Director functions as the Charlestown site's 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 with a much larger program.

The Assistant Site Director will support the Site Director in managing the following responsibilities:

  • 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 with the Assistant Site Director or Front Desk Manager to track student attendance
    • Working with the Assistant Site Director of Front Desk Manager 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
Required Qualifications:
  • 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 not essential but preferred; more advanced certification, or combination of equivalent certifications and experience a plus
  • Competency in driving a range of small outboard powerboats is helpful (e.g. center-console, 17' Boston Whalers and Easterns)
  • The ideal candidate would be interested in growing into the Site Director role and taking this position in 2016.
About Courageous 
Courageous Sailing Center is a unique and nationally renowned sailing center, headquartered in Boston's Charlestown Navy Yard. Our Charlestown site is a short walk from many different public transit options including the subway, buses, and commuter ferry. We use sailing as a platform to teach teamwork and responsibility, instill confidence and respect for the natural environment, and transform the lives of our city's youth. While famous 12-meter Courageous is no longer a member of our fleet, we now boast a fleet of over 70 vessels, including Rhodes-19s, J/22s, J/24s, 420s, Lasers, and an assortment of small cruising vessels. In 2014, over two thirds of our students received scholarship assistance or completely free summer programming, which included services like free meals, academic instruction, and swimming lessons.
Our Team 
Each year, Courageous hires nearly 100 seasonal staff and instructors. The Courageous 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 internationally renowned racers and seasoned cruisers. Our staff members also enjoy a wide range of benefits, including: racing opportunities, professional development support, connection to the growing Courageous alumni network, and the satisfaction of having a job that makes a difference.  We also hire experienced educators, naturalists, and outdoor educators who enhance our summer programs with their unique expertise.
Come spend your summer sharing your love of sailing, making a difference, and being part of an exceptional team of instructors who are united by their dedication to the mission of Courageous Sailing Center!
To Apply:
Visit www.courageoussailing.org/summer-youth-program-openings and complete our online application by answering a few questions and uploading your cover letter and resume.  We look forward to hearing from you!

Coordinator IIT Program


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.


  • Oversee all IITs and IIT program staff (22 students, up to 12 staff)
  • Make sure all students and staff adhere to the designated schedule
  • Organize and chaperone camping trips, BBQs, race nights, and other fun events for IITs throughout the summer
  • Complete MWBLP for all IITs and staff
  • Distribute evaluation surveys
  • 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


  • Bachelor's degree or currently in school for High School education, outdoor education
  • 3-5 years experience teaching teens
  • 2-3 years team management experience
  • 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


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
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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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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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Happy, Excited, and Free
Youth Program
For the past four years, I have had the privilege of working with students from Swim Sail Science, a program Courageous created in partnership with Boston Public Schools. The SSS program aims to serve students who are at risk of summer learning loss. These students continue their academic studies th...
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Pier 4, Charlestown Navy Yard, Boston, MA 02129



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