Delivered from Bristol RI to Pamlico River NC in 2017, great trip! Stopped in Connecticut first night. We timed the trip to deal with Hellsgate tide in NY, refueled the afternoon before at City Island, the Bronx, NY, fabulous Italian dinner a few blocks away..... Left at first light to catch Hellsgate 45 min after flood tide, got a nice, increasing comfortable push all the way well out of NY harbor from that and the confluence of the Hudson. Manasquan inlet in a Camano was a little spooky for me as a new owner, but I had the seller aboard and he was quite the pro on this and Cape May inlet the next day. Great dinner at Cape May, too. The marina we used at Manasquan was the one on the north side - last one before the railroad bridge. Yes, we heard trains that night. Cape May to C&O canal was a long day with a strong wind and following seas the whole day - semi displacement, flat after section - your larger boat will do much better.
Advice: Make sure you have fuel polished and a new fuel filters before heading out. I didn't, had to switch to back up Racor under way. Not a problem to do that, but might have not been cool if the pressure gauge pegged in the approach to an inlet. Sloppy seas as the wind built coming down from NY stirred up sediment/particulate from the bottom of the fuel tanks - fuel pressure gauge had not budged in the 4 days before winds off New Jersey. MY ERROR in not having fuel polished as part of delivery commissioning. (Surveyor, mechanic who changed oil, adjusted excess idle RPM, etc., didn't mention, but I should have studied more about risk factors before shoving off.)
One more tip - When I change old fuel filters, I cut them open with a hack saw to get an indication of what's in the fuel tank besides fuel. Delighted that a thorough polishing - 3x until the polisher filters were clean the last time - first thing back home from this cruise, and discernment about where I buy fuel has kept filters looking amazingly clean when I change them. I'd recommend that to anyone to check old fuel filters ....
Delaware Bay - we ran either in the shipping channel when no ships were in sight, or just outside of the shipping channel both for reduced snag risk and for maybe a little better ride than shallower water in the 4'+ seas. Schaffer's was a great place that night - live band, great crab cakes, helpful dock attendants, clean facilities. High winds encouraged us to put in on the Sassafras River the next day - found a great marina there - free luau that night treating transients as members. Stopped at Reedville - boat yard there, and Point Lookout Marina (Sunset Restaurant - Chef Andy's crab cakes were the best on the entire trip) on the Potomac were additional stops before entering Norfolk Harbor. There we found drizzle and light fog, kids racing small sailboats in the shipping channel around Thimble Shoal Light, Coast Guard med. endurance cutter and tug/barge all heading in the same time as us, and USS Kearsarge (small carrier) coming out to sea - nice time to idle and wait. Went straight through Norfolk to Top Hat marina on Elizabeth River-North Landing River cut - nice place. Anchored short of Belhaven the next day - a very long day with the Great Bridge lock and bridge, and a 45 min. wait at the Alligator Bridge. River Forest for fuel and nice walk in town at Belhaven before turning up the Pamlico toward home port.
Oops....too much information for your trip. Kent Island marina is a good place for a stop across the Bay from Annapolis if you don't want to transit the mooring field at Annapolis after sunset.
Good luck! Fuel polishing and new fuel filters on a new to you boat is the best tip in this.