NYC to Chesapeake Advice Sought
Hello...just completed the same trip. Don''t know what size boat/draft you have but from the sound of it you plan to sail "non-stop" down the coast and up the Delaware. Would suggest you put in waypoints for Manasquan Inlet, Atlantic City and Cape May...just in case the weather kicks up and try to time your turn up the Delaware to the tide as it can get nasty and long when wind and tide are opposed.
As to moorings...first, think about anchoring as there is great holding and many fine anchorages throughout the Bay. There are $20 per night moorings in Annapolis on Spa Creek on a first come first serve basis which should be open on weekdays at least at this time of year. Other than that...slips are prevalent in the bay with transient rates in upper bay running 1.50/ft on average except in annapolis...lower rates in lower bay. Hope this helps! //GB