Boat- and people-watching in Maryland’s capital city.

Navy-Themed Getaway to Annapolis
Credit: © NobleImages / Alamy

The Naval Academy and St. John’s College are in the middle of this small capital city, best known for its glittering harbor dotted with sailboats. A pedestrian friendly waterfront has sidewalk cafes and fantastic restaurants; nautical-leaning travelers can get around by water taxi.

Cantler's Riverside Inn

Just over the Severn River from Maryland’s capital, Annapolis, Jimmy Cantler’s Riverside Inn sits on Mill Creek, which empties into Chesapeake Bay, the source of the restaurant’s famous blue crabs. The main dining room and bar are all one could hope for from a watermen’s haunt: communal tables in a wood-paneled room decorated with marine memorabilia and photos of the Chesapeake Bay spanning the more than 30 years that the Riverside Inn has been operating. During the summer, the most coveted tables are on the screened-in porch overlooking the creek, each covered in brown paper upon which pots of steamed crabs are poured in front of diners. Blue crabs cooked in Old Bay seasoning are the restaurant’s specialty; order them along with a basket of hush puppies and corn on the cob when it’s in season.

Insider Tip: First, arrive early. On summer weekends, the outdoor tables fill up quickly. Second, while you’ll be handed a mallet to help you get to the meat inside your steamed crabs, ask a local for the secrets to opening up the shell of the crab. Most are eager to share their techniques with visitors.

United States Naval Academy

This prestigious school was founded in 1845. See what they mean by military precision at the noon meal formation.

Watermark Water Taxi

Hail down a red, green, or blue-topped water taxi for a ride to lunch, or just around the harbor.

Rams Head Tavern

Take in local microbrews, fish tacos, and indie bands in this locally loved restaurant housed in a redbrick colonial.

Scotlaur Inn Bed & Breakfast

Rooms may be on the small side, but this turn-of-the-20th-century row house has comfy beds with wrought-iron frames, and guests get a complimentary seat for breakfast at Chick and Ruth’s famous Delly downstairs.