Bonzai, this will be a terrific experience! I took our Com-Pac 27 up to Maine in 2012, mostly solo, all coastal. My wife wants to go this summer so we plan to shove off in mid-to-late-May, head up Chesapeake Bay and do it all again.
If you come up the ICW through the NC Sounds, I've heard good things about Elizabeth City, at the south end of the Dismal Swamp Canal. Friends recently did the Dismal, had no problems and lots of fun.
On Chesapeake Bay, highlights include: Hampton City Docks; Cape Charles Town Harbor; Fishing Bay or Jackson Creek, Deltaville; Tangier Island; Onancock (Eastern Shore Virginia); then in Maryland, Solomons Is.; Oxford; of course, Annapolis; Rock Hall; Sassafras River; and Chesapeake City on the C&D Canal.
On the Chesapeake, a favorable tide is nice but on Delaware Bay, it's mandatory! You can make Cape May in a day from the C&D (I recommend Utsch's Marina; nice family, reasonable rates; used it coming and going.) If you don't do an overnight, Atlantic City is probably your only choice as a next stop; Manasquan was easy in-and-out (pre-Sandy) if you need it. There's a good anchorage in a cove just around Sandy Hook; or at the east end of the breakwater at Atlantic Highlands. In either case, it's an easy run up the East River--with the tide, of course--and into LI Sound. I stopped at City Island when I got there.
Being a native Rhode Islander, sailing to Block and Newport was special but those both are great stops, no matter where one's from. I love Mystic but want to see Stonington this time. I'm sure I missed some good harbors on LI Sound in '12 so, like you, I'm looking for recommendations for that stretch.
I hope that's helpful and not too much. And maybe we'll see you along the way. Be well!
Bill
