Annapolis, Annapolis, Maryland
Concierge.com's insider take:
Founded in 1649, Maryland's state capital is a living museum of centuries-old shade trees, red-brick streets, and the greatest concentration of Georgian-style buildings in the country. Its street plan revolves around the domed State House, which dates to 1772 and could inspire an entire History Channel series: General George Washington resigned as commander of the Continental Army inside its Old Senate Chamber, where the Treaty of Paris formally ending the Revolutionary War was also ratified; in 1783-84 the State House also served as the capitol of the newly minted nation. When the current Legislature's in session, politicians often caucus at Chick & Ruth's Delly (165 Main St.; 410-269-6737; chickandruths.com), a friendly greasy spoon that keeps a special booth for Governor Martin O'Malley, a frequent customer. East of the State House is the campus of tiny St. John's College (1696), the third oldest college in America, and the U.S. Naval Academy. Exhibits at the latter's Armel-Leftwich Visitors Center (52 King George St.; 410-293-8687; www.usna.edu) include Freedom 7, the Mercury space capsule piloted by USNA grad Alan Shephard Jr., America's first astronaut. John Paul Jones, the heroic Revolutionary War skipper, is buried in an elaborate crypt beneath the Academy's neoclassical chapel.
Down on the busy waterfront, multimillion-dollar powerboats glide up "Ego Alley" to a small turning basin at City Dock, once a port for tobacco and slaves. Today most of the maritime activity in the self-styled "Sailing Capital of America" is found in Eastport, a working-class neighborhood of bungalows and boatyards just south of the harbor's forest of aluminum masts. Rent a boat yourself, or just watch them sail past while sipping cocktails at the dockside Pusser's Caribbean Grille.