Text by Katie Ellis
History is the draw for many visitors to Annapolis, Maryland. The city’s earliest settlers date back to the 17th century, and those who enjoy architecture will find Colonial touches at every turn, especially in the Historic District. But Annapolis is hardly old and tired. Midshipmen at the United States Naval Academy infuse a youthful energy, and travelers and locals alike congregate on the charming bricked-paved Main Street to visit the independent shops and restaurants. Because the city sits at the mouth of the Severn River on the Chesapeake Bay, the water culture influences much of its identity year-round and is especially scenic in the summer. You’ll see that best at City Dock, where beautiful sailboats rock easily in their slips, a scene that conjures up images of idyllic summer days on the water.
For the very best views of the city skyline, book a cruise aboard the Woodwind or Woodwind II, which sail daily from the harbor at the Annapolis Waterfront Hotel. Assist the crew in raising and lowering the sails on one of the 74-foot schooners—or just sit back and enjoy the ride. A stroll down Main Street is a must. Spend an afternoon getting lost in the local crafts shops and antiques stores. Don’t miss The Annapolis Pottery, where you’ll likely find potters throwing on their wheels as you browse pieces from both local and national artists. And of course, no trip to Annapolis is complete without a visit to the beautiful Naval Academy for stunning architectural sites and historic prestige. The campus has been an Annapolis icon since its establishment in 1845, and today, public tours allow visitors a glimpse into the history of the U.S. Navy. The Naval Academy Chapel is one of the most popular sites on campus, and all services are open to the public.
Break from the chain this summer and enjoy charming respite in one of Annapolis’s many quaint bed-and-breakfasts. The Georgian House, built in 1747, is just off Main Street and is one of the oldest homes in Annapolis. The brick Georgian-style house features wide-plank hardwood floors and a wonderful collection of antiques. Other cozy stays include The Annapolis Inn, Gibson’s Lodgings, and Chez Amis.
For a local staple, a visit to Chick & Ruth’s Delly is a must. The no-frills, diner-style delicatessen is often packed with a line out the door and is just as much about the experience as it is the food. If crab cakes and oysters are what you’re hungry for, you’ve come to the right place. Maryland is king of crab, making the choice for fresh, delicious seafood an easy option. Don’t miss Sailor Oyster Bar or Boatyard Bar & Grill. Finish off your meal with a delightfully chilly treat at Annapolis Ice Cream Company. Their 36 flavors rotate daily.