Full of colorful East Coast charm, Annapolis’ streets are lined with historic buildings, many of which date back to the 1700s. Overlooking the Chesapeake Bay, Annapolis is a seafaring town, and the popular things to do here reflect that—visit the on-campus museum at the US Naval Academy, stroll the City Dock to admire the passing boats, or take a cruise of the bay. If you haven’t got your sea legs yet, don’t worry: Annapolis has a bustling cultural scene with plenty of live theater, architectural landmarks, and excellent restaurants.
It’s hard to beat autumn on the East Coast, but Annapolis really comes alive in the spring. May is an excellent time to visit—the flowers are blooming, the days have started to warm, and the Chesapeake Bay is filled with sailboats. (Wednesdays are especially exciting, as the Annapolis Yacht Club holds weekly races throughout the spring and summer). The end of May also means it’s Commissioning Week for the Naval Academy, when students graduate and the whole town celebrates.
Historic Annapolis is compact and walkable, and it can be hard to find parking, but if you want to explore beyond the downtown, you’ll likely want to rent a car. The bus service isn’t particularly extensive, but Annapolis’ surroundings have plenty of cool spots (including the extensive Pennsylvania Dutch Farmers Market)!
On Wednesday and Saturday nights, the downtown end of West Street closes down for cars, and the restaurants open their doors to the street. Tables and chairs fill the sidewalks and road while strings of lights illuminate the scene—the perfect spot for a romantic dinner under the stars. From sushi to Mexican food to relaxed pub fare, there’s something for every palate.
