4 Best Restaurants in Annapolis and Southern Maryland, Maryland

Jimmy Cantler, a native Marylander who worked as a waterman on Chesapeake Bay, founded this local institution 40 years ago. The no-nonsense interior has nautical items laminated beneath tabletops, and steamed mussels, clams, and shrimp as well as a tomato-based Maryland crab soup, seafood sandwiches, crab cakes, and much more. Water-view outdoor dining is available seasonally, and boat owners can tie up at the dock; there's limited free parking during the busy summer season so be prepared to wait.

You can walk, catch a water taxi from City Dock, or drive over the Spa Creek drawbridge to this local favorite in Eastport. Whether you dine indoors or out, the view of historic Annapolis and its harbor is spectacular. Any of the entrées, including the herb-encrusted rockfish or grilled filet mignon, can be turned into a four-course meal with the addition of soup, salad, and dessert.

In the shadow of the state house, this understated establishment has long held a reputation for quality food and attentive service that ensures bustle year-round, especially during the busy days of the legislative session (early January into early April) and special weekend events at the Naval Academy. The menu clearly reflects the city's maritime culture, but also has seasonal specialties. The sidewalk café is open, weather permitting, April through October.

Popular with boaters who tie right up to the dock, this restaurant overlooking Island Creek has one dining room that actually juts out over the water and another on higher ground with great views from its floor-to-ceiling windows. There's also ample seating—and a tiki bar—outside. Stoney's hefty crab cakes are made with plenty of back-fin meat and little filler. Oyster sandwiches and Stoney's Steamer—handpicked selections of fresh seafood—are also good choices. The intense, house-made desserts, such as the strawberry shortcake and Kim's key lime pie, are not for the faint of heart. If you miss Stoney's in Broomes Island, there are two other locations in Solomons Island.