Annapolis is the sailing capital of the United States (there's a sign saying so right before the Eastport Bridge), so you must go sailing while in Annapolis.
- Another great thing to do is go to Sandy Point State Park and look at the Chesapeake Bay Bridge. There is a sandy beach, and it provides spectacular views and a view of an old lighthouse in the middle of the Chesapeake.
- Explore the historic district of Annapolis by foot. Walk with the colonial-clad guides of the Capital City Colonials as they tour you about town explaining the history, buildings, and colonial life in Annapolis' golden age.
- Lacrosse: Annapolis is generally considered to be the lacrosse capital of the U.S., with marquee matchups between high school powers St. Mary's and Severn taking place in the spring at the United States Naval Academy. Numerous nationally recognized junior and club teams also play throughout the year.
- Scenic drives: although Marylanders love the Chesapeake Bay, the majority of waterfront property is privately owned. As a result, very few scenic drives exist in Annapolis. The closest thing to an open drive is through Bay Ridge at the end of Forest Drive.
- Navy football: Although largely dormant since Roger Staubach's days, Navy football has enjoyed a Renaissance under Paul Johnson, and current coach Ken Niumatalolo. Still, even in a good season, the middies and their chants can be more entertaining than the onfield activities. Although stadium seating is often available, families with kids are known to prefer the North endzone, which is a grassy hill. The list of battles in which USNA alumni participated is always impressive, and leaves a strong impression. Be sure to be inside the stadium for marchon and for the weather permitting flyovers.
- Have some delicious Maryland crabs and crab cakes.
