Joey:
This year the Washington DC portion of my family is joining us on our annual pilgrimage to Gloucester, which has not happened since hurricane Bib struck. They have become huge GMG fans.
Do you know of anyone renting sailboats, small ones, for day sailing? I found only one, Cape Ann Sailing school, and the phone number on the site is wrong.
You probably have bigger fish to fry (or lobstahs to boil), but if you have any leads, please pass them along.
Good Morning Gloucester 
Don’t know if this helps, but sailGHS will take 4 people out for 2 1/2 hours. That includes a sailing lesson. 978-282-0954. Good luck.
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I took the SailGSH boating trip yesterday with my two grown children, for a $100 donation to their non-profit organization. It’s a worthy cause and is tax deductable.
Hilary was our crew member and she was very knowledgeable and personable. I would highly recommend it! For more info, Contact:
hilfrye@verizon.net,
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You could call the Harbormaster or the Eastern Point YC or Annisquam YC or Sandy Bay YC.
Also the Schooner Thomas Lannon takes out groups.
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