Annapolis, Maryland is a charmingly quaint and historic town that is within a half-day’s drive from most of the mid-Atlantic region. It’s the perfect destination for a romantic getaway, a sailing weekend or to try some of America’s best seafood.

Historic Sites in Annapolis

Annapolis was founded in 1649 and served as the capital of the United States after the Revolutionary War. In 1694 it became the capital of Maryland and is the oldest continuously used capital city in the U.S. The huge dome of the Maryland State House – the largest wooden dome in the U.S. – looms over the historic downtown area in stately elegance. Other historic buildings that are worth a visit include the Government House, home to the Governor; the Hammond-Harwood House, a 1700s Georgian mansion; the Chase-Lloyd House with its unique cantilevered stairway; and the William Paca House, the estate and impressively restored garden of the Maryland Governor who signed the Declaration of Independence. You can visit these vintage buildings on a self-guided walking tour or with a colonial-attired tour guide.

The brick streets are lined with well-preserved colonial buildings that house quaint shops and marvelous restaurants. The waterfront along the Annapolis Harbor is also a lovely place to stroll. The many sailboats with sails furled, bobbing at anchor and those racing in the wind far out in the Chesapeake Bay are testament to why Annapolis is known as “the sailing capital of the U.S.” Travel Maestro tip: A 40-minute boat tour of the harbor (in warm weather) makes for a scenic date or fun family outing.

The esteemed U.S. Naval Academy is adjacent to downtown. You can tour the campus to see the beautiful Tiffany windows in the chapel, the tomb of legendary John Paul Jones and Bancroft Hall, one of the largest dormitories in the world. When school is in session, you can watch the midshipmen march in formation every day at noon. If you get lucky, you might even see a wedding party exit the chapel beneath the raised swords of cadets. Travel Maestro tip: You absolutely must have ID to enter the Naval Academy.

Great Annapolis Restaurants

Foodies will find Annapolis to be a seafood paradise. It just doesn’t get any fresher than straight out of the Chesapeake bay! We particularly enjoyed a shrimp and crab gourmet white pizza and the tuna tartare at a hip little wine bar on Main Street called Red Red Wine.  Other restaurant options range from casual to elegant, moderate to pricey, so there are plenty of choices to please all tastes. Travel Maestro tip: Do not miss Chick and Ruth’s,  a locals’ favorite! It’s an old-style “delly” with a huge board of sandwich offerings, classic jumbo lump crab cakes that they’ll ship anywhere, and a six-pound milkshake challenge. We enjoyed gigantic omelets for breakfast, immediately after the whole restaurant was invited to stand and say the Pledge of Allegiance.

Where to Stay in Annapolis

Plan to stay two nights to experience all this charming destination has to offer. We chose the romantic and elegant Maryland Inn, one of the three Historic Inns of Annapolis. Rooms date to the revolutionary era, while the porches and lobby are vintage Victorian. The Governor Calvert House is a restored colonial and Victorian Inn with large conference facilities and the famous Hypocaust, the ruins of a unique greenhouse system visible through a glass floor. The Robert Johnson House is a 29 room guesthouse dating to 1773, furnish in antiques and reproductions.Annapolis is a delightful destination that takes pride in her role in U.S. history. To plan a short getaway to Annapolis, contact Covington’s expert vacation advisors for reservations.