Re: Sailing in New England for newbie
+1 on the Pelagic Sailing Club.
You can attend an open meeting without joining the club. The meeting schedule is published on their site, but they are on Thursday nights at the Savin Hill Yacht Club (Dorchester). I believe that they suggest a $5 donation.
Attending the meetings is the best way to get to know some of the sailors, and learn about crewing opportunities. They may even suggest that you take an introductory sail with an experienced member. They will not, however, want you to continue sailing with their members without your joining the club (<$100/year).
I will probably re-join this year because I have the time.
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USCG Licensed OUPV Captain, ASA 101/103/104/105 Certified Instructor - Also certified in Recreational Marine Electrical Systems