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.

Step inside this Irish pub, and you'll be welcomed like a member of the family. As would be expected, the corned beef and cabbage and other traditional Irish menu items (along with classic Annapolis bar food like crab and oysters) are fantastic. The bread pudding served with vanilla custard is a great way to end your meal. On Sunday, brunch is served from 10 to 1:30—the homemade corned-beef hash is simply divine—and live Irish music is performed 4–8.

There's often a line of hungry diners waiting for a table at this comfort-food haven located on the city dock, where the portions are generous, and the service is first-rate. You can enjoy breakfast all day—Benedicts and omelets are top sellers, as are the chicken and waffles and the shrimp and grits. If you've saved room for dessert, try the homemade peanut butter cup or the "shortcake" made with a Belgian waffle and topped with ice cream, strawberries, and whipped cream.

This might be the only local Italian restaurant that doesn't offer pizza or spaghetti. Instead, Osteria serves seafood from all over the world, meat, and pasta made on the premises. Northern Italian owner and chef Arturo Ottaviano offers authentic regional cuisine like grilled branzino filleted table-side and beef tenderloin with a cognac-and-green-peppercorn sauce.