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Annapolis to Newport
I agree totally with GB''s post--very comprehensive. However, another question is whether you are interested in dinking and dawdling, or is it delivery-mode and try to get up there reasonably quickly.
I have made the trip often, but usually more into delivery mode than dawdling.
So, my 2 cents: If dinking around, there are places to stop in Northern Chesapeake, like Sassafras River. Also a nice restaurant on the C&D northern side (the name escapes me for the moment)--fairly high end restaurant, and the tide current at their docks goes past quickly. You can also anchor near the east end of the canal for a short period to wait for tide headed down the Delaware if you wish, but stay away from the freighter channel. If this is your first transit of the C&D, prefer to do it in daylight, if possible. ANd watch for the freighters, some that go through there are huge. Not much to do on the Delaware before Cape May. It is really much nicer, as GB mentioned, to go in from the bay side if your mast height allows. On a 54 we had to go around, on a 35 we made it through--check the charts carefully. One word of caution--the Delaware is a pain in the neck sometimes. The channel is narrow and many freighters go down it, be careful of shoals off channel. When the wind and tide oppose near the mouth of the bay, there is a short chop that is annoying, especially if you are going around.
Cape May is nice for either lunch or staying a day or two if you are dawdling. I have hit fog fairly often right at Cape May and up to Atlantic City--so be prepared for it. Atlantic city is very nice to stay at. There is a marina right at one of Trump''s casinos and it is a fun break.
In the past we have gone from there directly to Statue of Liberty, anchored, then headed for Hell Gate. GB already mentioned the tide. I have gone around Long Island and through the Sound and prefer the Sound.
Enjoy the trip. You get a bit of everything--from old towns (like Cape May), freighter traffic, canal, big city (NYC), etc. It is probably 3-4 days if you move quick, could be anything if you dawdle.