Here's a way to break up the trip to give short offshore legs and allow for safer, shorter weather windows.
1. Down Long Island Sound
, down the East River and through NY harbor. Cautions: time your trip through Hell Gate for slack or ebb tide. It can run 5 kts reversing so if you have it against you, you would be almost sitting still. There are lots of places to stop at the west end of LI Sound so you can wait for proper departure time for the E River.
2. After passing NY Harbor you can anchor
at Gravesend Bay or behind Sandy Hook. From there it's about 120 nm to Delaware Bay so at 6 kts about 20 hours. So if you leave NY around midday you should make the entrance to Delaware Bay the next morning. Seems like most people go into Cape May but I stopped across the bay at Lewes DE. I took 5'4" draft
into the town canal with no problem. If you need fuel
there's a small but nice marina about 1/4 mile in on the left and a restaurant next door. We topped off the tanks
and they let us stay free while we had lunch next door. Very friendly little town. If you don't want or need to tie up you can anchor
at the mouth of the bay at the harbor of refuge.
3. If you want very protected water
for the next leg you go up the bay to the C&D canal that crosses over into the upper Chesapeake Bay
then down the bay to Norfolk where you enter the ICW. I preferred going outside again as I had a tight schedule. Outside from DE to Norfolk is about the same distance and strategy as the leg from NY to DE.
4. One you get into the ICW you are in protected water
the rest of the way. There are a couple of sections that are a bit open like crossing Albemarle Sound.
5. Once in the ICW you will have to watch close as at places the channel makes a twist and a turn and you don't want to shortcut between two markers.
6. The section that may be a bit tricky is GA where there is a 9-10' tidal range in spots leaving some places in the channel as low as 3-4' at low tide. Here you will have to play the tides or go outside.
Good luck on the trip. Lots of great resources to check out including the Waterway Guide (books and online), Cruiser's Net online cruisersnet.net, and Active Captain
online. Or if you have questions feel free to PM or give me a ring.