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Re: Route from Maine to North Carolina
I've made all the parts of this trip. Some of them 20 times or more. Here's my suggestion for routing. How many stops you make will depend on wind, weather, tide and time, and number of crew.
Here are some options:
Saco to Cape Ann (good anchorage at Rockport outside the harbor by the beach), or
Saco direct to Provincetown (good anchorage just inside Long Point).
Provincetown to the CC Canal (20 nm) can be timed to get the beginning of the fair current through the canal, or even better, time it so you get the last three hours or so of the fair current so when you come out the other side you won't have to worry about the wind vs current that can cause problems. There's a "harbor of refuge" at the east end of the Canal where you can wait for the fair current if your timing is off.
Once in Buzzard's Bay there are several good places to stop -- Onset (as mentioned before), Pocasset, Hadley Harbor on Naushon Is., Cuttyhunk are all places I've stopped for the night. There are many more.
From the south end of Buzzard's Bay you can sail direct to Block Island easily in a day. If you have a headwind, make for Point Judith or Newport. From any of these places you then head into Long Island Sound and, once again, you will have an easier time if you time the current correctly. Buy a copy of Eldridge for good info on currents in this area.
Fisher's Island is another stop just beyond Block Island on the other side of the race off Montauk. There are many places to stop in LI Sound, but it's important as you get toward the west end to pick a stop that lets you get the fair current through Hell's Gate and into the East River, down the harbor and to the anchorage at Sandy Hook in one shot.
As for sailing outside LI, I'd recommend the inside route not just because it's easier, but because motorsailing through NYC is a hoot.
Sandy Hook, below the Verrazano Narrows Bridge, is a good overnight stop. Next, go direct to Cape May or stop in Atlantic City depending on timing. Take the canal through Cape May to avoid the bars at the entrance of the Del Bay. Time departure from Cape May to ride the current up the Del River and into the C&D. Time it perfectly and you can ride a fair current all the way arriving at the entrance of the C&D Canal at slack water, just as the current turns to let you carry a fair current through the Canal as well. There are several places to stop on each side (and in the middle) of the C&D canal if need be. Then cruise down Chesapeake Bay to Norfolk, enter the ICW there and a two days later your home.
If all this will take too long, an overnight Saco to CC canal will save time -- as will a long sail down Buzz. Bay and into LI sound. LI Sound itself can be one in one shot by sailing overnight. Sandy Hook to the Chesapeake via Del River can also be done non-stop if you watch the timing -- one critical part here is getting the current running up the Del. River. Chesapeake Bay can also be done without stopping.
September is a nice time to sail throughout the route, but keep an eye on the tropics and map out the hurricane holes before you go. There are several along this route and they should be well researched before leaving.
If the weather is settled and you have fair winds the easiest way to cut several days off is to go from Block Island to Cape May (200 nm), but you'll give up the trip through NYC.
As for places to stop on the outside from Cape May to Norfolk -- others would know better than I, but I don't think there are many with easy all weather entrances. The trip up to the C&D Canal and down the Chesapeake is longer, but stops are easier to find and in September it should be a nice time to cruise in this area, especially later in the month when it begins to cool off a bit.
As for going outside around Cape Cod....it's longer and the only possible tough spot (west end of the CC Canal) can be avoided if you watch the current and wind carefully. It is true that Buzzard's Bay can be a tough slog in SW25, but there are plenty of places to stop to avoid foul winds and currents should they arise.
Another factor in route selection is that if this is a new boat (new-new, or new-to-you?), you'll be breaking it (or you) in and/or learning its character/moods. That's a good reason not to strike out on the offshore route, but to plan your track so you can easily stop along the way to fix anything that might need fixing. Another reason for taking an inside route is that you'll get a feel for the cruising grounds to your north and you'll most likely want to come back.
It's a nice trip...enjoy it.