The sightlines in Annapolis are punctuated by colonial spires and white sails. Every walk through the narrow alleyways of Maryland's capital is a journey back to the 18th-century. The city's well-preserved cobblestone streets and squat, brick red Colonial architecture may inspire you to dust off your tricorne and square buckled shoes. A maritime life flows at the rhythm of the tides, evidenced by schools of yacht traffic bobbing at the waterfront or Naval Academy midshipmen strolling downtown.

Things to Do
In summer, the bars and restaurants of City Dock feel like one big boating party, lit by the blaze of sunset on the Chesapeake Bay. On a carriage ride through downtown, watch the colonial mansions and row houses come to life. Venture to the nearby National Cryptologic Museum for a glimpse of how spies made and break codes. The story of slavery, the speeches of Frederick Douglass, and the region's African-American history are on display at the Banneker-Douglass Museum.

Nightlife and Entertainment
Come indoors to the local pubs for an earful of sea lore and a pint. The Rams Head Tavern will fill your glass with Fordham beer, a local craft brewer. Stick around for a set of folk music. Every night of the week, 49 West Coffeehouse, Winebar & Gallery hosts music -- jazz, classical, or folk. You can also counter a chilly sea breeze there with something warm and view the work of local artists.

Restaurants and Dining
Welcome to a seafood pantry of plenty. The centerpiece here in the Chesapeake Bay is the blue crab, a surly small beast whose meat is flaky and slightly sweet. The locals mix blues with breadcrumbs, pepper and spices in crab cakes, a fried or broiled regional delicacy. Carrol's Creek wins accolades for its harbor views alone, but its soothing cream of crab soup and seafood entrees eclipse the waterfront scenery. Boaters swear by the fresh catches at Cantler's Riverside Inn.

Active Pursuits
Learn to sail from the pros: The Annapolis Sailing School is the oldest in America and offers programs for novices and experts alike. If you'd rather be a passenger, board a 74-foot schooner for a tour of the Chesapeake. Landlubbers can take in a ghost tour of the city and its many haunts or a stroll through the terraced gardens of the Charles Carroll House. At noon, the midshipmen line up in formation for inspection -- a visitor's highlight.