Re: Dinghy Sailing in New York City? Possible?
I took instruction with NYC Community Sailing and then sailed with them for a couple of summers. They keep their 27' Solings at the Lincoln Harbour Marina, on the Jersey side of the Hudson, just south of the Lincoln Tunnel. Weekend days they match up experienced skippers with newbies, 3-4 to a boat, and go out for a few hours.
I now have a Precision 185 I keep at an inland lake. It would be very difficult to manage something as small as my 18 1/2' boat on the Hudson - the currents, tides, cruise ships, barges, tugs, sightseeing boats make it very busy. I don't think the Honda 2 HP I have would be a match for those currents.