Incorporated in 1708, Annapolis MD is a colonial capital with a rich history. Located at the mouth of the Chesapeake Bay, this thriving city is a national center for sailing, annually drawing thousands of boating aficionados from around the world.

Things to do in Annapolis

Annapolis is a treasure trove for history and architecture buffs, with many of the city’s 18th century buildings listed on the National Register of Historic Places. Erected in 1772, the Maryland State House is the largest legislative building in the U.S. still in use today. Other highlights of Annapolis historic sites and museums are the Banneker-Douglass Museum and the Kunta-Kinte Alex Haley Memorial, overlooking the harbor where Alex Haley memorialized Kunta-Kinte’s arrival and subsequent sale. It now has a bronze sculpture of Mr. Haley telling his story to bronze children rapt with attention.

You can rent boats, kayak, stroll the historic streets, take the walking tour or plan your own. Try the water taxi to take you from downtown Annapolis to Eastport or even to your boat, if it’s anchored in the harbor.

Visitors planning to stay more than a day or two can pursue a number of day trips, including a jaunt to nearby Solomons Island, as well as enjoy excellent local theater, restaurants and shopping.

The United States Naval Academy

The Annapolis Naval Academy (USNA) is the second-oldest service academy in the U.S., educating the nation’s finest midshipmen since producing its first class in 1854. Held every year in late May, USNA Commissioning Week, traditionally known as Naval Academy June Week, is the week-long celebration that graduates another class of Naval Academy Midshipmen to the ranks of Naval Officer and removes the stigma of “Plebe” from the 4th Class. There are dances, parties, and traditional events at the Naval Academy. The climbing of the Herndon monument is exciting. This event is open to spectators and it’s something to witness. The Plebes attack the greased obilisk to see which of them will capture the cover (hat) on top determining their stratospheric climb to the top of the Navy’s ranks. The Ring Dance is a favorite, when 2nd classmen get their class rings. The midshipman’s date wears the ring around her neck and together with her midshipman dip it in water from all seven seas. This is not a spectator sport, however so you’ll just have to hear the stories! The famous Blue Angels flying demonstration is another must-see — and can-see. This event actually spans over two days as the Blue Angels practice one day before their actual performance. People line the banks of the Severn River and drape their legs over the Naval Academy Sea Wall. You can get tickets on public boats to watch the performance from the water as well as join friends and family on private boats. Make sure you make your hotel reservations well in advance, however, as Annapolis fills up. If you are associated with a graduating midshipman, then check out the whole house rental options. Annapolis Accommodations offers many homes where you can be within walking distance to the USNA and all the festivities and still have the benefits of a home where you can eat, sleep, and entertain. This is a tradition in Annapolis, MD where local homeowners rent their homes out for Commissioning Week to the families of graduating First Class Midshipmen and one that benefits the USNA, the families, and the Town.

Annapolis Restaurants

The Annapolis Waterfront provides numerous opportunities for dining on local seafood. Annapolis is world-famous for its Chesapeake Bay blue crabs, as well as fresh oysters and fish. Like any other large American city, Annapolis has become a melting pot of culture, resulting in a comprehensive selection of international cuisine.

Annapolis Shopping

The revitalized Downtown Annapolis is a center of culture, commerce and industry. Within walking distance of the USNA, the shopping on Main Street and Maryland Avenue ranks among the best in eastern Maryland. The Westfield Annapolis Mall has over 240 stores and restaurants to satisfy any other need you may have. If you want to try other options, you can check out the boutiques in Eastport, the shops and restaurants in the Annapolis Harbour Center, or the new restaurants and stores at the Annapolis Towne Centre just off of West Street and Riva Road.

Annapolis Events and Annapolis Boat Shows

The equivalent of Mecca for serious boaters, Annapolis hosts two of the nation’s most prestigious boating events. The Annapolis Sailboat Show is the largest of its kind in the U.S. The annual Powerboat Show highlights the industry’s newest in high-performance boats, yachts and boating gear. Both are in-water and offer miles of floating docks and gorgeous boats and boating accessories to fill you mind for days. The food vendors offer lots of mouth-watering food options. Of course, the downtown Annapolis restaurants, although pretty busy, offer your favorite seafood and other cuisines.