Set on the Severn River in the heart of the Chesapeake Bay, it is home to the U.S. Naval Academy, it’s the state capital of Maryland, as well as the Sailing Capital of America – it’s got more history wedged into a few compact blocks than most places multiple times its size will ever be able to claim (George Washington really did sleep here) – and it’s a boater’s paradise.

Annapolis is also home to charming, bricked streets lined with one-of-a-kind shops and restaurants. It has more 18th-century buildings than anywhere else in the U.S. The State House is the oldest in continuous legislative use in the country, the homes of three of Maryland’s four signers of the Declaration of Independence are open to the public. Because Annapolis’ historic sites are so close to one another it’s an easy destination to explore.

Boating here is a way of life, and it’s a singularly great place to visit with your vessel. There are many marina options (note: reserve ahead, especially on summer weekends), and you can even drop anchor at a mooring ball right in front of the Naval Academy, then catch a water taxi into town. No matter where you tie up you won’t be able to miss the action at Ego Alley, the locals’ name for City Dock, in the center of town, where showboating captains come to strut their stuff.