What I have done, not necessarily what you should do.
I've done the trip 6 times (3 each direction) in a 36'
sail boat (50' air
draft, 6'
water draft) with just myself and my wife. We are relatively inexperienced off shore sailors compared to many others here. We are not in a hurry. We tend to try for 24-48 hour offshore hops, then a couple days or longer hanging out.
Most of this is similar to Carlf and it will depend on your mast height.
Florida to Charleston. We
anchor in the Ashley river upstream of the bridges and by the park with the free
dinghy dock. You will likely not be able to get that far up as there is a 56' fixed bridge, but there are
anchorages below that bridge. Read active captain/waterway guide
reviews as there may be some debris on the bottom in those
anchorages.
Charleston to Beaufort.
Anchor across from the town marina. Or you can anchor up Taylor creek, but it's tight. Or, just go into the bight.
ICW from Beaufort to Norfolk. We find this ICW stretch generally pleasant and there is some sailing to be done in the Neuse River and while crossing the sounds or Alligator river. Empty, quiet anchorages along the way. We usually stop at the free docks (free is at the high end of my
price range, in case you couldn't tell) at the locks.
Norfolk to Cape May, sometimes leaving from the locks, other times staging closer to the mouth of the Chesapeake depending on weather windows.
Cape May to someplace near
NYC depending on if we are going up LIS or staying offshore of LI. Depends on the weather and seas and if we want to go overnight. Sometimes we go straight through the city and stop in Port
Washington. We have also anchored in Coney Island Creek, but it's pretty sketchy in terms of junk on the bottom and toxic sludge that comes up on your anchor. Well protected though.
NOTE: You need to consider the currents going through the East River.
NYC-ish to Narragansett Bay. If we are lazy we will take a couple days going down LIS. Watch the currents at The
Race. If weather cooperates will will just follow the south shore of LI then
head for the Bay.
Hope that helps.
Another Roe Dylander