Sailing Instructors and General Sailing Staff

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

Sailing Management
Job Start Date
Job End Date
Application Closing Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
From $14.00 To $20.00
Per Hour
Employment Type
Part Time
Work Schedule
No Travel

Job Description
Courageous Sailing, a community sailing center located in Boston, MA, is looking for skilled instructors, program managers, powerboat drivers, and dock staff through October 31, 2019.

We are seeking experienced sailing instructors looking for non-traditional summer hours or a flexible work schedule. Instructor responsibilities may include but are not limited to:

-Taking up 4 individuals on 2 Hour Cruises on Boston Harbor on weekdays
-Private Lessons
-Assisting with running races/mark boat on Tuesday and Thursday evenings
-Teaching adult Learn to Sail participants on weeknights or weekends
-Assisting members with rigging/de-rigging
-Assessing sailing ability of new members
-Qualified candidates may also be asked to oversee sites during opening/closing procedures

Flexible scheduling can be tailored to accommodate individual availability throughout the duration of our season May 1-Oct. 31.

All positions involve working as a team to promote a safe, positive and fun learning environment for students; being a knowledgeable ambassador for Courageous Sailing and the sport of sailing; and exercising good judgment in challenging situations, both on and off the water.

Benefits of working at Courageous include free access to our fleet of Rhodes 19s, J/22s, J/80s, dinghies and cruising boats, and being part of a community of sailors working together in support of a great cause.
Job Requirements
Strong sailing and teaching skills
Positive and enthusiastic attitude
Ability to work some nights and weekends
Strong motorboat skills preferred
Experience in College Sailing and/or Keelboat programs a plus
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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