Life in the beautifully-preserved ‘Sailing Capital of the U.S.’ revolves around one thing: its rich maritime culture. Sitting at the heart of Chesapeake Bay – the largest estuary in the country – the charming state capital of Maryland is abuzz with seafaring glamour. From the countless boats that line its City Dock, to the U.S. Naval Academy students strolling through the cobblestoned streets in their starched white uniforms, maritime heritage is everywhere you look. Tour the Naval Academy, which has been training officers since 1845; explore funky boutiques and soak up some sun as you sip a coffee at City Dock; learn all about America's sailing legacy at the National Sailing Hall of Fame; or dine on the freshest Maryland blue crabs in a waterfront eatery.