Caroline & Jonathan
Things To Do
United States Naval Academy
The United States Naval Academy is a beautiful academy adjacent to Annapolis. Established in October 1845, under Secretary of the Navy George Bancroft, it is the second oldest of the United States' five service academies. The campus is located on the former grounds of Fort Severn at the confluence of the Severn River and the Chesapeake Bay.
Annapolis Harbor
Relaxing at City Dock is a main reason why people visit Annapolis. Take in the sunshine while enjoying one of several dining establishments and watching boats cruise in and out of Ego Alley. It's also the launching point for most of Annapolis' water tours. Whether you’re dining, boutique shopping, or simply looking to relax by the water, City Dock is a lovely way to spend a morning, afternoon, or evening.
Boatyard Bar & Grill
Located in Annapolis' historic Eastport neighborhood, this place tops almost every crab cake there is. Fun nautical vibe and good eats, you'll be alongside sailors, boaters, fishermen and others enjoying the Boatyard's casual ambiance!
Stroll Down Main Street
Historic downtown Annapolis is a vibrant 21st-century neighborhood with 18th-century charm. A walk down Main Street puts you in touch with four centuries of preserved architecture. There's a contagious energy here; look in any direction and you'll find something to pique your imagination - the Chesapeake Bay, Midshipmen in dress whites, historic landmarks, boutiques and yummy restaurants. Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks & views of the harbor.
Maryland State House - The Oldest U.S. State Capitol
Completed in 1779, this was the site of nationally important events during the American Revolution, including George Washington's resignation as commander in chief of the Continental Army from the army, and the ratification of the Treaty of Paris.
McGarvey's Saloon & Oyster Bar
Long-standing (since 1975) tavern offering dozens of craft beers plus a raw bar & pub-fare menu.
Chick & Ruth's Delly
Authentic throwback amazing diner and an Annapolis institution. An unassuming exterior, local great spot. Amazing crab cakes, authentic charm and tradition. The Pledge of Allegiance is recited every morning at 8:30 sharp!
Schooner Woodwind Sailing Cruises
Raise the sails in the heart of the Chesapeake Bay, in Annapolis. You can steer the boat or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and along the Chesapeake. The captains and crew are engaging and enthusiastic. Sail away!
Annapolis Marine Art Gallery
Since the year 1979, this gallery has provided the best of marine art to the Mid-Atlantic collector community. Located at City Dock in Annapolis, it is open seven days a week to the public. To have a look at some beautiful, nautical watercolors don't miss this gallery!
The Point Crab House & Grill
Wonderful outdoor dining on the water. The Point Crab House offers great, casual, neighborhood dining producing fresh & local Maryland/Chesapeake dishes. Known for having the best Maryland Crab soup!