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My $.02 worth:
Don't do the trip if you aren't competent and equipped to sail the boat in most any weather, and navigate, and have competent crew as well. Three is probably minimum.
Rent a life raft. Get a handheld radio that really is waterproof. An EPIRB is probably a good idea also. Make sure you are equipped for and proficient at man overboard maneuvers.
It is now Autumn, and still hurricane season. You must watch your weather and have contingency plans. If it looks possible for a storm to interfere with your trip, don't wait to do the contingency plan. Survivors chicken out early.
Outside the Cape is a stretch of nothing but a shoal beach. What harbors there are are shoal and difficult to approach. You must be prepared to stay well offshore while transiting this area, no matter what. Having said that, it is not a bad trip IF the wind is NW and there isn't fog. I'd hang in Provincetown for nice weather and make sure that my fuel tanks were full.
Clearing Nantucket Shoals is a similar deal. Stay further off than you think necessary and don't place too much faith in charted depths in this area. Not bad with NW wind and the right weather. If you run into fog, however, your navigation had better be top notch and your engine needs to run flawlessly. You'd also have some experience in the stop (the engine), look, and listen drill and other measures that are necessary when in reduced visibility.
Those northwesters can blow pretty good in the Fall, and if so, you may have a pretty steep sea to deal with. Your trip will probably either be beating against a SW or reaching/close reaching before a NW wind. Fatigue and seasickness are formidable foes. You and your crew must be ready for them.
You will cross the approaches to New York whether you take the CC Canal or not. The prudent navigator never relies on the deck watch in a larger vessel. Don't get close to them. Slow or stop if necessary.
Finally, there is and can be no guarantee of safety. Be prepared, or just take AmTrak.
Last edited by Goodnewsboy; 09-24-2007 at 10:03 PM.