Considering taking Bebop, but would be more likely to trailer if we go. If I were to sail, I'd want to leave at least two weeks ahead in case of foul weather and to give myself a chance to recover from the trip. Not everyone has that kind of flexibility. In all but calm weather the Delaware Bay and the Atlantic can be hard on the boat and taxing for the crew.
You probably won't have the crew weight on the rail you have while racing, so upwind and reaching plan on using an old Dacron #3 or #2 Genoa if you have one and have the main ready to reef. Send your racing sails up by car. Be sure your engine is in tip-top condition, bring spares, start with a clean fuel tank and a fresh filter. You are likely to motor even when sailing particularly in Delaware Bay and the East River/Hell Gate. Timing the tides for these two locations is critical as the current really rips.
We did two round trip deliveries Annapolis to Long Island and Annapolis to Newport back in the days of Loran. Cappy, my dad, did not like to sail all night or get too far offshore, so our route was intended to allow us to sail during the day and anchor or tie up night at whenever possible. Annapolis to Chesapeake City on the C&D, then time the tide to Cape May. Through Cape May Canal which cuts distance and is a good place fuel up and wait for a weather window for the leg to New York City. Have also stopped at Atlantic City inlet. I have been in an out of Mansaquan a few times, but not in a J/30. It might be dicey in rough weather. Once when I still lived in NYC we stopped overnight at South Street Seaport. Likewise for City Island which is not fair off the rhumb line about 30 NM from Cedar Point.
As always Bill K is a great resource and a meticulous planner. As a Navy grad Bill may know it by another name but I've always thought it was Greenbury not Gooseberry Point in the Severn River off Annapolis.
