Dock and Dine: Annapolis, Maryland Restaurants to Visit by Boat
In addition to the history, sailing and scenery, Annapolis offers some excellent waterfront dining. Restaurants, bars and cafés serving steak, burgers and authentic Maryland seafood (plenty of Old Bay, please) can be found around the waterfront.
Whether you’re in town for a weekend, visiting from Baltimore or cruising over from a private boat dock rental in Kent Island or St. Michaels, docking and dining at a local eatery always makes a fun outing. Try some fresh seafood, have a drink, listen to live music and enjoy views of the Severn River, Whitehall Bay and the Chesapeake Bay.
Pusser’s Caribbean Grill
Photo: Pusser's Caribbean Grill Facebook
If you like the tropical ambiance of the British Virgin Islands, you’ll want to check out Pusser’s Caribbean Grill. Located on the Ego Alley waterfront on Annapolis Harbor, it grew from the original Pussers in Road Town, Tortola. It has been voted Best Dockbar Restaurant by What’s Up Annapolis. There are slips available on-site, or you can dock at Annapolis Town Dock and walk around the historic district before or after dinner.
Located next to the Annapolis Waterfront Hotel, the restaurant opened in 1994 and serves breakfast, lunch and dinner. Selections include pasta, seafood, filets, pizza, seafood and more with a Caribbean twist. There’s a large cocktail menu as well as wine and regional craft beer. And, yes, you can get one of those famous Pusser’s Painkillers. Dine inside or outdoors by the docks. Visit the company store for nautical and BVI souvenirs. Pick up a bottle of original Pusser’s Rum and enjoy those BVI vibes.
Mike’s Restaurant & Crab House
Photo: Mike's Restaurant Facbook
Open since 1958, Mike’s Restaurant & Crab House is famous for its traditional Maryland-style seafood. Dine on Maryland crab soup, grilled tuna, Jamaican jerk chicken, pizza, New York strip and seafood platters. Located on the South River, there’s free boat dockage and lots of parking for the landlubbers. Check out the company store to buy ice, refreshments and menu items to go. Entertainment includes karaoke nights and live music.
Latitude 38 Annapolis
Photo: Latitude 38 Facebook
Latitude 38 Annapolis serves beef, chicken, burgers and seafood such as rockfish, salmon and tuna. Enjoy waterfront views of Annapolis Harbor while sipping on a specialty cocktail, house wine or specialty craft beer. It’s next door to the United States Naval Academy and across the creek from the Annapolis Boat show site. Boat docking is available along the waterfront.
Yellowfin Steak and Fish House
Photo: Yellowfin Steak and Fish House Facebook
For Sunday brunch, head out from a private boat lift rental to Yellowfin Steak and Fish House. If you’re not brunching, enjoy steaks, fish, sushi, pasta, flatbread pizza and views of the South River views. The restaurant is located at Oak Grove Marina, which has a fuel dock, a ship store and picnic areas. Docking is available at the nearby Liberty Marina. Let them know you’re dining at Yellowfin.
Chart House
Photo: Chart House Facebook
Chart House, on Spa Creek in downtown Annapolis, has a unique vantage point to watch sailboat races, regattas and other boats cruising around the historic harbor. The building, formerly a boat house, was the main shipyard for John Trumpy & Sons. Enjoy upscale seafood, New York strip, herb-roasted chicken and Sunday brunch.
We hope you’ve found some new restaurants to check out the next time you’re boating in Annapolis or looking for something to do from a private boat slip for rent. Let us know if we missed any!
