Other thoughts on Bay Sailing
Not sure when you plan your trip, but a couple of pieces of local knowledge may be of help.
Once it warms up the Eastern side of the bay seems to have more insects, particularly green head flies and misquitos. You don't have to get far to the East to see the effect.
As Tom pointed out the less deep areas the current will be less of a issue. Once north of Baltimore the ship channel moves to the East in part to clear the restricted water around Aberdeen Proving grounds. If traveling north on a week day you have to stay East of Pooles Island which is a a shame if you stop in Baltimore or any of the rivers around it, all of which offer good dockage and protected anchorages. The route to the west of the Island is shorter if you are making for the north and more shallow but again can't go there Monday through Friday.
Again depending on when this trip actually is crab pots can drive you crazy. At night they can make anything other than the ship channel an ordeal if the moon is not bright. Since it sounds like you plan to move in daylight may not be an issue.
We made a run to Cape May now about four years back the Delaware current is stronger. We had a great time but as can often happening our planning for the tide didn't work. We got a late start out of Chesapeake City, due to fog, which is common. We got to the river about 2.5 hours later than we planned. We had planned to get into the river about an hour before the tide changed unfortunately we got there after. Then the wind dropped to nothing and our flea powered YSB 12, never had 12 hp even at the factory and certainly not 30 years later, barely moved us a knot above the current. For a grand finanle the wind came back straight up the river at about 15 near sunset and we fought it the remainder of the ride to Cape May.
I am sure the Delaware River Sailors with more knowledge that can chip in but the only points I would offer on that are there are no protected anchorages other than the Cohancy River our boats can get into from the C&D till Cape May or Lewes so its either plan on the Cohancy or plan to make the trip in one shot.
Also the entrance to Cape May from the River has a long break water and the night we did the run light on the Red Mark that marks the entrance was out. Looking at the chart we were convinced it wasn't the entrance It was a heavy chop and heavy cloud and if the bow look out had spotted the break water its likely we would have sailed right into it.
Moral of that story is in unfamiliar waters keep someone awake and watching the front. The cockpit would not have been able to see it in time to drop sail put on the engine and fight the wind.
