Where to Sail in NY
For me, there''s no contest - Long Island Sound is it. The Hudson and Upper New York Bay have strong currents which, when opposite the wind, can have you beating against steep waves at 6+ knots and not moving over the ground at all. While the scenery is spectacular, it can get old.
Currents on the Sound (at least most of it) are generally weak. there are plenty of bays and coves within easy daysailing reach and, if you''re more ambitious, you can just keep going east until you hit Nova Scotia. Just cruising within the Sound itself can last a lifetime.
I keep my boat on City Island which is about 30 minutes from Midtown and, if necessary, reachable by subway (#6 to Pelham Bay Park) and bus or express bus. The Yacht Clubs on City Island also have a very active racing program, which you can be part of without joining any club. We have boats of all sizes up to 55'' schooners, so depth is no problem.