There are different criteria. There is best water view. There is best food. And then there is the most fun for those looking for a more party venue. On the Chesapeake, you are most likely to get 1 out of the 3. Often enough 2 of the 3, and that's the thing to shoot for. Never 3, because party fun doesn't mix well with fine dining, but if avoidance of party is the goal then yes, there can be 3.
I am most familiar with the Kent Island area of the Chesapeake, because I have a home in the area. The funny thing is, land lubbers always ask me about a restaurant and rave its the best and most memorable place ever for them. It used to be Hemmingways until about 2 months ago, now Libby's. It sits directly on the Bay, adjacent to the Chesapeake Bay bridge on the Eastern Shore side. The food has always been "OK" or a notch better, but nothing special to locals. But it has a major WOW factor for those who don't see a sunset over the water very often.
Better food is down the road at Kentmore, where the food is good, but served up in simple surroundings. Outstanding fried oysters in the winter.
More down home, and local. Nice tiki bar on the beach that is just pleasant without getting wild at all. Parking is impossible, if arriving that way, and the marina entrance appears challenging though I've not tried that approach.
Another spot in the Kent Narrows area favored by land lubbers is Bridges. Clean, upscale, and sit along the dockfront, the food probably a 3.5 on a scale of 5.
Meanwhile, killer cuisine is to be had yards away at The Narrows, which is where the locals will go every time for fine dining / white tablecloth sort of place. As fine a crabcake as you can find. Perfect steaks. Best gazpacho I've ever had, served in the summer. Be sure to order fried green tomatoes as a side dish. The soft shell crab salad is pretty good too.
Because its a Bay specialty, some look for "crab houses" where cracking hard shell crabs is the primary attraction. Harris Crab House, and Fisherman's Crab Deck would get an equal nod.
A new restaurant just opened a week ago. On my list to try soon. Co-owned with the family that owns Fisherman's so it should be no less than OK.
I won't get into dock bars with loud rock music.
In Annapolis, a lot of good things come together at the Annapolis Yacht Club. If invited by a member, accept the invitation. Great view, wonderful tone to the place, and excellent food. Apart from that, the better food in the town, that I know of, is off the water but generally close enough. Lewnes Steakhouse in Eastport is an example.
And all 3 come together in Ocean City Maryland. The marina just inside the inlet is Martha's Landing. (Note: you know you are talking to a local if they refer to it as Stinky Beach", because that's what the vacant property was called before being developed maybe 20 years ago.) The fine dining is excellent in all respects with a marina view. If you are more of a party mood the dock bar is upscale and active. This is a spot (both dock bar and fine dining) favored by upscale locals, for good reasons. The interesting thing is how they manage to hit quiet fine dining, and dock bar, on the same property, and nail it with both.
