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The "NYC area" is a pretty vague term. It sort of goes from perhaps Nyack, on the Hudson, down to Sandy Hook, and from Brooklyn through Hell Gate up and out to Long Island Sound. The WW 15 is a fine boat, but probably isn't well suited to the conditions you'd find in most of that territory most of the summer sailing season. Typical southwest breezes that might be nice and strong in Sandy Hook or even in NY harbor itself get diverted by the city's thermal updraft and don't come down again until they get to Connecticut - often the other side of New Haven. The Hudson might fare somewhat better, but generally wind is light in much of this area. The WW15 has a relatively small sail area for such conditions. It will sail, but might not perform as well as another boat with bigger sails. Powerboat wakes can make sailing an undercanvassed boat very frustrating. If that's the boat you have and you need trailerability, you can make it happen. There might be other boats better suited to the conditions you're likely to come across, however.
 

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Long Island Sound has lots of interesting places to visit within range of a weekend cruise for you. You will want to work with the current to get in and out of the World's Fair Marina, or you will spend a lot of time not getting much of anywhere. Buy a copy of Eldridge's Tide & Current book and make sure your motor is in good shape with plenty of fuel. Fair winds!
 
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