Chesapeake Shore: Colonial Capital & Maritime Maryland

The 1779 State House is the oldest in continuous legislative use — the national capital for 14 months (1783–84), where Washington resigned and the Treaty of Paris was ratified. The surrounding streets follow the original 1695 Baroque street plan: the brick rowhouses on Maryland Avenue and Prince George Street are among the finest concentrations of 18th-century domestic architecture in America, largely intact because Annapolis declined economically after Baltimore rose in the 1790s and thus avoided the 19th-century redevelopment that destroyed similar fabric elsewhere.

The Academy's 338-acre Yard is open to visitors and the Preble Hall museum covers naval history from John Paul Jones (whose crypt is beneath the Chapel) through the present. The Bancroft Hall dormitory — single largest dormitory building in the world at 1,700 rooms — can be toured on guided visits. The cemetery on the Academy grounds holds the graves of admirals, Medal of Honor recipients, and astronauts Alan Shepard (class of 1945) and Edgar Mitchell (class of 1952).

An upscale Italian restaurant on Main Street widely regarded as the best dinner option in Annapolis — the housemade pasta, the branzino, and the Italian wine list have drawn Zagat attention since 2005. Reserve well ahead for Friday and Saturday evenings.

The 18-acre waterfront museum campus in St. Michaels is the definitive institution for Chesapeake Bay maritime culture. The collection includes nine historic vessels — skipjacks, bugeyes, and log canoes — that once worked the Bay's oyster beds, along with the 1879 Hooper Strait Lighthouse relocated to the campus. The boatyard conserves and builds traditional Chesapeake wooden vessels using traditional methods, and you can watch the work in progress.

St. Michaels was founded in 1677 and retains a compact historic district of 18th and 19th-century Federal and Victorian buildings along Talbot and Cherry Streets. The town is most famous for a possibly apocryphal 1813 incident in which residents hoisted lanterns in the trees to mislead British naval gunners into overshooting the town — the 'town that fooled the British.' Drive 12 miles further on MD-33 to Tilghman Island for working waterman culture and skipjacks at the dock.