I did the reverse trip about his time last year. Helped a friend move his sailboat from Sandy Hook down the NJ coast, then up the bay, into the Delaware river to Essington Harbor. We left from Sandy Hook Friday evening about 6:30pm, sail down the NJ coast about 3 to 6 miles off strait through. There was three of us rotating a two man watch. Rounded Cape May point about 6:30pm Saturday evening into a run up the Delaware Bay, arrived at the mouth of the C/D Canal about 6:00am Sunday.
Unless you intend to only stay in marinas
, there are some nice anchorage areas along your route
through the upper Chesapeake. Once in the canal there is only Chesapeake city or summit north marina. Delaware city gets its share of transient sailors, but because of bridge clearances on the branch canal, it can only be approached rom the Del. river I've sailed the area from Baltimore up through the Elk river, canal and Delaware bay extensively.
In case you may not be aware, the C&D Canal can only be motored through. Not sailed. Once through the canal there are anchorage areas up river of the canal exit behind Pea Patch island and down river behind Reedy island. To wait out the tidal current.
About mid way down the Del. bay there is an abandon light house base just north of the shipping
channel. Its charted, but not marked or lighted; Also there are not any good harbors to run to if the weather kicks up until you get to Cape May or Lewis Del. Just off of Cape Henlopean, Del. There is a large stone breakwater that forms a harbor of refuge that gives safe anchorage in any weather. Avoid the Cape May canal unless your sure of your mast
Depending on when you are making the trip. If you would like some additional experienced crew. Send me a PM.