Annapolis may be best known as the state capital, but its real charm lies in its deep maritime history, walkable streets, and Chesapeake Bay lifestyle. Founded in 1649, Annapolis served as the temporary capital of the United States in 1783 and is still home to the oldest state house in continuous legislative use. A visit to the Maryland State House, where George Washington famously resigned his military commission, offers a direct link to the early days of American democracy.

The U.S. Naval Academy sits right along the Severn River and is a central part of the city's identity. Visitors can take guided tours of the historic campus, including stops at the Naval Academy Chapel and John Paul Jones' crypt. During the academic year, it’s not unusual to see midshipmen in uniform making their way through downtown. Watching the precision of the Brigade of Midshipmen’s noon formation on weekdays is both free and memorable.

Annapolis is often called the Sailing Capital of the U.S., and for good reason. The city’s harbor is filled with sleek yachts, historic schooners, and working watercraft. Annapolis Harbor and Ego Alley offer great views and even better people-watching. For a hands-on experience, visitors can hop aboard the *Woodwind*, a 74-foot schooner featured in the movie *Wedding Crashers*, for a sunset sail with views of the Bay Bridge and city skyline.