Hey Chris,
Just discovered the BLACK DOG CAFE at Dodson's Boatyard in Stonington, CT last November, great place, wonderful atmosphere...
LUCKY BONES in Cape May... and if you're up for a stay in a marina, South Jersey Marina is one of my favorites anywhere, really great spot... Lots of great eating spots in downtown Cape May, if you should linger there for awhile...
The CHESAPEAKE INN in Chesapeake City on the C&D canal... I've only eaten in the bar there, but the food and drinks were great...
HILDA CROCKETT'S CHESAPEAKE HOUSE on Tangier Island, a classic... Haven't been there in probably 20 years, however, so it may have changed...
COINJOCK MARINA RESTAURANT in Coinjock, the quintessential ICW marina/restaurant... One of my favorite places, anywhere... Hard to define what makes it special, but it always has been, to me...
In Morehead City, right near the Yacht Basin, a place called FLOYDS... Superb dining, at reasonable prices, could be one of the very best restaurants along the entire ICW... If in Beaufort, I usually go to the SPOUTER INN, though the FRONT STREET GRILL is excellent, though higher priced...
THE RIVER ROOM in Georgetown, SC has always been a nice treat...
THE GREYFIELD INN on Cumberland Island... Another place I haven't been to in a long time, not sure they even serve anymore to walk-ins... (they definitely require advance notice) A very special place, unfortunately became famous after JFK Jr. got married there, and is now likely to be VERY expensive... Still, might be worth checking out, as I'm sure you know Cumberland Island is well worth a stop...
Downtown Melbourne FL has become quite the trendy spot, lots of great pubs and restaurants along the Main Street there...
The HARBOR COVE at Harbortown Marina in Ft. Pierce has always been one of my favorites... Nothing fancy, typical marina restaurant, but always good specials at reasonable prices...
In Lauderdale, if you anchor in Lake Sylvia, take the dinghy thru the canal to the west, across the ICW, and down to the end of the canal to the SOUTHPORT RAW BAR, or THE QUARTERDECK just across the street... Again, nothing fancy, but very popular crew and sailor's hangouts, great pub food, burgers, etc...
Then there's Miami Beach... I have really come to love the anchorage behind near Monument Island/Venetian Causeway, largely due to the convenience to Lincoln Road and all of Miami Beach... An endless array of great eating spots withing walking distance of wherever you tie up your tender in the canal, you could easily spend a week or more just sampling restaurants alone... As you probably know, this can be a difficult anchorage, the currents can really swirl around in there and create weird wind against tide situations, etc... I usually anchor off Monument Island by myself, less current out there, but you'll be subject to a lot of wakes, and the scene there on weekends gets pretty crazy... Lots of spots to re-anchor, however, and I can never quite get over the fact that I'm allowed to anchor right in front of Madonna's house, while enjoying the spectacular Miami skyline at night, and the free Miami Beach wi-fi... If you have to wait for the weather to cross over to the Bahamas, this is the spot...
If you get down into the Keys, THE LORELI on Islamorada is my favorite sunset bar/restaurant - good food, and great music, nice blend of locals and tourists hanging out... It's on the back/Florida Bay side of the keys, however, and could be a problem with your draft unless the water in the Bay is up...
Good luck, and best regards,
Jon