We will be in Cape May this evening, contemplating the trip to Annapolis. There doesn't seem to be any good stops up Delaware Bay. But it looks like you can carry the tide most of the way up, even into the canal. There seem to be two marina choices inside the canal. If I go around the odd shoals off of Cape May, it is about 78 miles to Chesapeake City - a longish day, but doable.
On the other side, there are numerous rivers, bays and marinas, for the most part far too shallow for our 6.5 ft draft. But it is only 48 miles on to Annapolis. I haven't checked the currents there, but I assume one could carry the tide most of the way down.
What is the normal prescription for this trip?
The strong NW winds the next couple of days don't look appealing for Delaware Bay, supposed to blow west by Tuesday if you believe them (and I have lost all faith).
Cape May looks like it has two marinas deep enough, and maybe an anchorage off the coast guard dock. Any recommendations?