First off I’ll leave it up to you as to how to escape New York.
There are two ways that I would travel since you are thinking of taking 95.
The first route I would take is 495 around Wilmington De to 13S, which is rite before 495 merges with 95. Take 13S though New Castle, 13S and route 1 merge at the route 40 light, just stay left, down to 896. Make a right on 896 to 301, it is well marked and there is a Wawa on the left at the light. Take 896 to 301S, you will only be on 896 for a couple of miles and the intersection has a light. Make a left on 301S, travel thru Middletown De and a couple of miles you will enter the Peoples Republic of Maryland. 301S will merge with 50 W and take you over the Bay Bridge. Depending on the time and day most traffic will be going east to the shore. This will take you into Annapolis. This route has no tolls and is flat and level.
The second way would be take 95S into Md. Take 695E/S to the Key Bridge. Then take 97S to 50E to Annapolis. This route has tolls. There will be a toll on 95 in De, and a toll at the Key Bridge. And there are hills on 95 from De to Baltimore.