I sailed NY Harbor, professionally, every summer, since 1987.
Contrary to one commenter, size does matter! Not so much for the sailing but the absolutely necessary horsepower to motor
against the current
of the Hudson
River and tidal flow both inbound and outbound.
Smallest I recommend is a Catalina
22 with a 9.9 hp, even better a C-25 with a 15.
Big applause to the comment "join a local sailing school
." Generally speaking, you're going to be on a J-24 and limited to the lower Hudson
and upper bay. No LIS, primarily because the East River is no place for even advanced new sailors
due to hellascious currents and large, limited in maneuverability tugs, barges.
Winds are delightful in the upper bay. Prevailing southwesterlies all summer about 12 to 18 and the skyline view from the water