Rating: 4.6/5 stars (5,084 reviews)
Address: 400 Fourth St, Annapolis, MD 21403, United States
Overview: The Boatyard is a local favorite for sailors and seafood lovers, serving refreshing drinks, delicious crab cakes, and the freshest seafood. Highlights include on-site smoked fish of the day, cream of crab, Maryland crab soups, and a range of seafood specialties.

Rating: 4.5/5 stars (4,097 reviews)
Address: 12 Market Space, Annapolis, MD 21401, United States
Overview: At Iron Rooster, you can enjoy breakfast all day, lunch, dinner, and drinks with a fresh twist on traditional comfort food, all served with legendary hospitality. We’re Makin’ Bacon every day and invite you to come experience our warm sense of community for yourself.

Rating: 4.6/5 stars (2,310 reviews)
Address: 410 Severn Ave, Annapolis, MD 21403, United States
Overview: Situated along Spa Creek in the Annapolis Marina complex, our waterfront restaurant boasts views of the Naval Academy and downtown Annapolis. Enjoy a menu filled with fresh seafood, hand-cut steaks, and fine American cuisine, open for lunch and dinner daily.

Rating: 4.8/5 stars (988 reviews)
Address: 909 Bay Ridge Ave, Annapolis, MD 21403, United States
Overview: Vin 909 Winecafe features over 40 thoughtfully curated New and Old World wines by the glass, alongside a selection of microbrews and small-batch beers. We pride ourselves on using farm-fresh, organic ingredients in our ever-changing seasonal menu.

Rating: 4.7/5 stars (673 reviews)
Address: 177 Main St, Annapolis, MD 21401, United States
Overview: Osteria 177 embodies the essence of an Italian tavern, featuring imported delicacies and unique food and wine as the main attractions. With a selection of local specialties, spices, cheeses, fish, and meats, it offers an authentic culinary experience.

Rating: 4.5/5 stars (522 reviews)
Address: 310 Third St, Annapolis, MD 21403, United States
Overview: O’Learys Seafood Restaurant is renowned as the top fresh-fish seafood spot in the region and the best in Annapolis. Located off Spa Creek with views of historic Annapolis and the U.S. Naval Academy, it features fresh seafood and an excellent small wine list.