...Ship John Shoal Light is almost 25 nm from Delaware City, 50 nm round trip, a long day at my typical 3 to 4 knots, so maybe another time. Its about 5 nm from the Cohansey...
I wasn't thinking of doing a round trip to Ship John from Delaware City. I thought you had suggested that on Saturday we go from Cohansey to Ship John Shoal Light, then up to Delaware City. That's very doable, and might still permit time to go to Chesapeake City instead. So here's what I'm suggesting, which I think is just a minor tweak from your original itinerary (but I haven't checked the currents yet)
Friday May 3: Essington to Cohansey River on ebb. Be sure to leave early enough to enter Cohansey with daylight, preferably on flood or slack.
Saturday May 4: Cohansey to Chesapeake City hopefully by dinner time, with side trip down around Ship John Shoal Light if winds, current, weather, and daylight permit. If we are short of time, just go straight from Cohansey to the canal.
Sunday May 5: Quick motor through the canal to Delaware City. Timing depends on current in the canal.
Monday May 4: Super early departure from Delaware City back to Essington on flood.