Bareboat Cruising Instructor


Job Description

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    • Teaching sailing on Boston Harbor - not a bad way to spend your spare time
    • Compensation: $15/hour for US Sailing-certified Keelboat Instructors; $20/hr for certified US Sailing-certified Cruising Instructors with USCG license
    • Free membership for instructors who commit to teaching at least 4 full Basic Keelboat classes during the season. Check out our website for details, but this means free use of the fleet and access to all member racing, events, parties, etc.
    • The chance to have a really good time, become a better sailor and better teacher, and be part of a great organization.

Current US Sailing Keelboat/Cruising Instructor certification is Required.


    • US Sailing Level 1 or Keelboat Instructor Certification, equivalent or more advanced
    • Current First Aid/CPR certification
    • Passing sailing checkout with Head Cruising Coach or Sailing Director
    • CSC 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 I certification course)
    • 1-2 years experience teaching sailing
    • Exposure to basic sailboat and engine maintenance
    • Must be available for occasional overnight cruises and island campouts
    • Positive and enthusiastic attitude
    • Self-starter with strong work ethic and attention to detail
    • Team-oriented
    • Outstanding references
    • A passion for sailing, cruising, the ocean, the environment and working with youth  

Other Considerations for this position 

    • Other certifications (Lifeguard, EMT, WFA, WFR, etc.)
    • Prior experience with out-of-school, outdoor, or experiential education
    • Previous experience cruising Massachusetts Bay and surrounding waters a plus
    • Camping experience


Apply to be a Bareboat Keelboat Instructor


Cha O'Connell, Director of Adult Programs

Phone: 617-242-3821 ext. 17





Friday, 09 January 2009 13:34

Bareboat Cruising Course

Bareboat Cruising (40 hours)

Prerequisite: Basic Cruising or equivalent experience. Participants must be experienced in basic navigation and maneuvering cruising boats (24+ feet) under sail and power. Green Flag rating recommended for Courageous members.
Optional US Sailing Certification Fee: $75
Included Text: US Sailing Bareboat Cruising
Regular Price: $895
To purchase and schedule a course, click Book Now. To purchase a course and schedule it later, click Buy Now
To schedule a course that you've already purchased, click Book Now and enter your voucher code as the Promotion code.

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Once you start sailing the bigger boats, it’s hard to stop! And there’s always more to learn. Our Bareboat Cruising course is the next step. It picks up where Basic Cruising leaves off and covers topics such as navigation, anchoring, and heavy weather sailing in much greater detail. You’ll learn the things you need to know when chartering a sailboat: the various techniques used around the world for mooring and anchoring (e.g. stern and bow, fork, Mediterranean, Bahamian); controlling the boat under power with confidence; big boat docking techniques; provisioning; visiting the fuel and pump-out dock; VHF communication; and more. We will also take you through a tour of all the important boat systems, peering behind seat covers and into the bilge until you know exactly where everything is, what it does, and what to do (or who to call!) when it doesn’t work. This course typically includes 3 days of sailing, two overnights at anchor or moored, and additional prep and debrief time. Maximum of 4 students.

Many course participants choose to test for their US SAILING Bareboat Cruising certification, which signifies that you have sufficient skills and knowledge to safely and confidently skipper an auxiliary powered cruising sailboat between 30’ and 45’ in length, in winds above 15 knots, within sight of land during daylight hours. This certification is widely respected and accepted by many sailboat charter companies in the US and other parts of the world.  Most Bareboat graduates are also qualified for a Courageous cruising membership.

Passing this course qualifies the student to apply for their International Proficiency Certificate. This is needed if they wish to bareboat cruise in the European Union (EU).




Courageous Mainsail Partners


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