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Re: Sailing outside on the East Coast
That time of year, you'll want to choose your rounding of Hatteras carefully. Your best choices are simply to motor around during a calm, or try to ride down the beach in advance of a frontal passage while the breeze is still SW-W-NW... You must be very confident of the forecast and timing of the frontal passage, however, as you definitely want to be around Diamond Shoals before the wind moves to the N-NE... In between the Steam and the Outer Banks is not a good place to be, once that happens...
There's considerable risk to this route, and some like Don Street will insist that one should never round Hatteras inside of the Stream... I disagree with him there, I think leaving from the Chesapeake and running down the beach is an acceptable risk if you're patient enough to wait for the right weather... I'd suggest passing the Cape during daylight, I've always cut right around the red nun "2" right off Diamond Shoals with no problem... But again, that is not a place you want to have anything go wrong, especially if weather builds from the NE... Once around the shoals, the bight of Hatteras could afford some protection as a place to heave-to, but it's still a long haul down around Cape Lookout, don't even think about Hatteras or Ocracoke Inlets as a bail-out option in bad weather...
If you're gonna go down the coast as far as Jacksonville, I think you may as well proceed as far down as Lake Worth, Lauderdale, or Miami, and cross from there... Unless you are blessed with exceptionally favorable weather, I just don't see any real advantage to heading for the Bahamas from a spot like Jacksonville... Further north, a place like Charleston, perhaps, actually makes more sense, generally...