Re: Dinghy Sailing in New York City? Possible?
I sailed a Wayfarer/CL16 when I lived in Ontario but I'm now sailing on Halifax Harbour. I wouldn't want to be out in the harbour in a dinghy for all the reasons previously mentioned. I imagine New York harbor would be even more challenging.
My solution was to buy a Colgate 26 daysailer. As noted above by petercech they are the boats used by the Offshore Sailing School in Jersey City and you can join and rent their boats. They are a beautiful sailing boat almost dinghy like in their handling but with the stability and safety that a keel and outboard offer. It has certainly expanded my sailing horizons and would be an opportunity for you to try something different.