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I’m thinking I would like to tweak my abilities on my boat and am looking for recommendations for an instructor
Don’t care if they’re ASA but why not
My boat is in Eastern Bay
 

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I took classes at annapolis sailing school, and the instructor said he could do this (he was "Freelance"). You can probably call them and ask for contanct info for their instructor. I remember seeing that Sailtime in annapolis also offered this
 

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S2 7.9 Bear Lake, UT
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Don’t care if they’re ASA but why not
My boat is in Eastern Bay
Call the local sailing schools or reach out to marinas or boat dealers to find an instructor locally. I think it makes sense to have an ASA instructor so the things you are learning are standardized.
 

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As around at local yacht clubs or racers associations. You have Kent Narrows YC across the Narrows from you.
May be tougher right now with the Covid restrictions
 

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The ONLY thing that ASA standardizes, in terms of learning, is the written test. You could go to two different schools for any ASA course and have a very different learning experience.

If you don't care about ASA certifications, I would find a local instructor (ask at sailing clubs for references) and hire her/him directly. Most ASA instructors will provide private instruction on your boat for $300-400/day. If you go through a school for instruction on your boat, you will pay considerably more for the same instructor, and the instructor will make considerably less.
 
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I would tweak the question to "What do you look for in an instructor to work with you on your boat?"

I don't necessary have any answers myself, I would like to hear the collective wisdom from the forum.

Jim
 

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Learning the HARD way...
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Things that I want from an instructor;
  • someone with experience (have them show you their Merchant Mariner Credential [MMC], and ASA or US/Sailing ID card
  • someone that I can get along with
  • someone that has prepared notes that they will share with you (aids to learning)
  • someone that can provide a reference (ask for a sailing resume)
 

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The ONLY thing that ASA standardizes, in terms of learning, is the written test. You could go to two different schools for any ASA course and have a very different learning experience.
Having taught in many different environments including sailing but summer camp does not count. Some sort of standardization counts as well as teaching skills. Not all USCG Captains will have this skill but possibly market themselves as a teacher.

I hired a guy to work with my wife so she was more comfortable sailing just the two of us. He did help us in that regards but he also showed her how to hoist a mainsail by wrapping her hand in the halyard to get more leverage. Even she knew better than that. A person without any sailing experience may take that as an appropriate way to handle lines on a boat.

Reminds me of the joke: What do you call the guy who graduates last in his class from Medical School?

Doctor. Not all Captains/instructors are created equally.
 
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