Sailing Instructor, Youth Programs- Summer 2019

Courageous Sailing, Inc.
Pier 4 Charlestown Navy Yard
Charlestown, MA 02129
United States

Job Start Date
Job End Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
From $12.00 To $14.00
Per Hour
Employment Type
Summer Only
Work Schedule
Summer Only
No Travel

Job Description
Courageous Sailing operates an extensive summer program for youth ages 8-18 at three different sites throughout the Boston area. At our main site on Pier 4 in Charlestown Navy Yard, we have a five-step program that takes students from basic classes through Instructors-in-Training (IITs) as well as a program that provides free sailing, swimming and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond and Camp Harbor View sites which offer beginner level sailing opportunities. Our instructors are skilled sailors who act as role models and function well as a team. We teach on a variety of boats including Rhodes 19s, RS Quests, 420s, and Lasers. Please find the descriptions of each step and other summer programs on our website, all for which we are hiring sailing instructors.

• Positively engage with and supervise students on-the-water and on-land
• Sail in boat with students
• Teach students basic sailing concepts and how to sail the boat
• Teach sailing safety
• Lead and participate in safe, fun and engaging activities on-land
• Help facilitate student feedback surveys
• Help complete student progress reports
• Follow directions given from Head Instructor and Asst. Head Instructor
• Attend all 5 days of staff orientation
• Attend staff meetings
• Be a constructive and amiable member of the Courageous team
• Maintain a fun, positive, friendly atmosphere
• Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person
Job Requirements
• Exceptional sailing ability
• Current First Aid/CPR certification
• Experience as a sailing instructor preferred
• Positive and enthusiastic attitude
• Outstanding communication and team management skills
• Excellent references
• A passion for sailing, the ocean, and working with kids

2019 Mandatory Dates:
• All Staff Training: June 24-28
• Monday-Friday 8AM – 4PM, from Monday, July 1 – Friday, August 9
• Staff Retrain Day: Monday, July 22
• End of Season Staff Day: Monday, August 12
• Additional work is available Tuesday, August 13 – Friday, August 23
• All staff are eligible to request up to 3 vacation days
Employer Contact Information
Courageous Sailing, Inc.
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
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Our Mission

Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.

Our Vision

Courageous Sailing is a community that embraces sailing as a platform for life-long learning, personal growth and leadership; a center of sailing excellence committed to removing barriers to access for all Boston youth, the public and people with physical and intellectual challenges.


Courageous Sailing was established in 1987 as a 501(c)(3) by the late South Boston sailing enthusiast Harry McDonough. It was Harry’s dream to use sailing to build character and camaraderie among Boston children from all economic and ethnic backgrounds. For 25 years, we have continued to grow and deliver our mission to transform children’s lives through sailing programs that inspire learning, personal growth and leadership. In Harry’s words, “Every child's perspective is improved 50-yards off-shore.”

Courageous is now a nationally recognized year-round educational center for community sailing and youth development. Courageous offers Boston-area youth free and low-cost out-of-school-time programs in sailing, environmental education, job skills development, and leadership training. In 2011 we were honored to be named one of the top 10 community sailing programs nationwide by both US Sailing and Sail Magazine.

How Courageous Got Its Name

The America's Cup 12 meter "Courageous" once lived at Pier 4 in the Navy Yard. This two-time America's Cup winner lent its name to Courageous Sailing in the late 1980s. The boat now resides at the Museum of Yachting in Newport, Rhode Island, where it has been restored and is still being raced.

Employment Opportunities

Join a team of nearly 100 seasonal instructors, administrators, and coaches, all dedicated to delivering affordable, high quality sailing programs to thousands of Boston-area community members each year. Visit our website to view our most up to date job postings and to find the right opportunity for you. We look forward to hearing from you!

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