Five Things to Do in Annapolis, Maryland

An easy day trip from Washington, DC, Annapolis once also enjoyed the spotlight as the capital of the United States, albeit briefly. Today most people visit this colonial enclave to stroll the leafy streets lined with boutiques and cafes as well as to soak up the amazing views of the Chesapeake Bay. No matter what you choose to do, you are almost guaranteed to enjoy a relaxing weekend in one of America’s great small towns.

1. Go sailing

Annapolis’ position on the water has made it a city of strategic importance for centuries. Even today the U.S. Naval Academy is located in town, ensuring that this long maritime tradition continues. For civilians it’s easy enough to enjoy some solitude on the Bay by chartering a sailboat for the day or enjoying an evening out on one of the dinner cruises available.

2. Self guided walking/food tour

There’s nothing I enjoy doing more in Annapolis than taking a stroll around the old streets and narrow cobbled alleys that make up the historic core. The main street features dozens of locally owned boutiques and shops specializing in everything from furniture to sweets. The walking circuit will take you past the old church and the architectural marvel that is the State Capitol Building. Believe it or not, no nails were used in its construction, making it even more impressive. Along the way don’t forget to stop at any of the many restaurants and cafes for a quick snack or early meal.

3. Ghost tour

Annapolis is one of the most haunted towns in America, a fact even many locals don’t know. This has led to a ghostly cottage industry of tours and walks to discover the spooky side of town. My favorite is the classic ghost tour around Annapolis. Led by a local expert, the two-hour tour is a great way to see the town at night and learn more about its early history. Plus you never know what you’ll see along the way. For the more socially-oriented, there’s a haunted pub crawl also available.

4. US Naval Academy

Founded in 1845, the U.S. Naval Academy enjoys a prominent spot in Annapolis at the confluence of the Severn River and Chesapeake Bay. The massive, 338-acre complex is home to many historic buildings and is itself a National Historic Landmark. Public tours are available from the Armel-Leftwich Visitor Center and include a video, visit to the museum and a walking tour of the grounds. Be sure to check with the Academy in advance for the current schedules.

5. Stay the weekend

While Annapolis is a fantastic day trip for visitors to Washington, DC, it’s also a wonderful spot to spend a romantic weekend for locals and tourists alike. Instead of the many chain hotels, be sure instead to check into one of the beautiful bed and breakfasts around town, many of which are housed in historic homes. My favorite is the Academy Bed and Breakfast located just steps from the waterfront and the center of town. This recent addition to the B&B scene in Annapolis is the labor of love of owner John who spent years bringing this great building back to life. If location is everything, then there’s no better choice than the Academy B&B.

No matter what you choose to do in Annapolis, you’re guaranteed a relaxing, laid back weekend in America’s forgotten capital.

Note: Available plans and coverages may have changed since this blog was published.