Annapolis Girls' Day Out Annapolis is such a charming town, perfect for a girls' day out or a weekend escape! It offers fantastic shopping at one-of-a-kind boutiques, delicious dining options, local art galleries, and opportunities to cruise the Chesapeake Bay, all set in a beautiful waterfront location. What's not to love? Here are the top 8 things to do I recommend for an amazing day or weekend in Annapolis with your girl crew, or really anyone you like to spend time with.