Cruising Instructor- Summer 2019

Courageous Sailing, Inc.
One First Avenue
Boston, MA 02129
United States

Job Start Date
Job End Date
Application Closing Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
Employment Type
Summer Only
Work Schedule
Summer Only
No Travel

Job Description
Courageous Sailing is looking for a Cruising Instructor to join our staff and participate in coaching within Adult and/or Youth Programs during the summer of 2019. Position can include participation in both or one program based on schedule and availability preferences.

Adult Program:
Position Summary:
Courageous Sailing, a 501(c)3 nonprofit engaged in sailing education for Boston youth and the community, seeks US Sailing certified Cruising Instructors to teach courses and private lessons, May 1st through October 31st. Most classes run on the weekends and weekday evenings. Hours are flexible and pay rates are to be commensurate with experience.


-Teach US Sailing Basic Cruising and Bareboat according to the curriculum as laid out by US Sailing and Courageous Sailing
-Provide a safe, positive and fun learning environment for students
-Conduct check-out sails for new cruising members
-Private Lessons
-Lead small groups during corporate events
-Act as a liaison between membership and maintenance to ensure proper care of the cruising fleet.
-Be a knowledgeable ambassador for Courageous Sailing, Charlestown, Boston Harbor and the sport of sailing
-Assist members in planning overnight sails
-Exercise good judgment in challenging situations, both on and off the water

Youth Program:
The Keelboat/Cruising Coach works with a group of up to 6 Step 4 students. Step 4 is a combination of dinghy sailing on 420s, RS Quests, Lasers, and performance cruising in our J/80s. Students focusing on cruising will be learning how to handle a sportboat, tweak sail controls for maximum performance, fly an asymmetrical spinnaker, and navigate safely in Boston Harbor. The Keelboat/Cruising Coach will also serve as a resource for the Instructors-in-Training trainers.

• Lead Courageous J/80 sportboat programming for Step 4 students and Instructors-in-Training.
• Responsible for between 15-30 students both on-land and on-the-water
• Lead a team of up to 2 sailing instructors
• Prepare lessons and on-land activities when sailing is not possible
• Lead safe, fun and engaging activities both on-land and on-the-water
• Lead conversations in which students reflect on their experience
• Work with the Dinghy Coach to organize weekly staff dinghy racing series
• Manage student transitions between activities
• Help lead and supervise an overnight camping trip for Step 4 students
• Maintain a fun, positive, friendly atmosphere for your students
Job Requirements
• USCG Captain's license
• Extensive J80 or comparable sportboat sailing and racing experience preferable
• 2-3 years coaching/instructor experience
• US Sailing Keelboat Instructor or equivalent certification; (for Adult Program) US Sailing Basic Cruising Instructor or Bareboat Cruising Instructor certification preferable
• Racing experience and knowledge of the Racing Rules of Sailing
• Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
• Current First Aid/CPR certification
• Positive and enthusiastic attitude
• Outstanding communication, team management, and positive behavior management skills
• Excellent references
• A passion for sailing, the ocean, and teaching

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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