Annapolis, Maryland

"Waterfront Chesapeake dining. Crabs and sailboat views."

Carrol's Creek has been the go-to waterfront restaurant for Annapolis for decades — Chesapeake blue crabs, rockfish, and oysters served with views of the harbor and the Naval Academy across the creek.

"Annapolis institution since 1965. Politicians and midshipmen eat here."

Chick and Ruth's is one of Maryland's most beloved diners — sandwiches named after politicians, a daily Pledge of Allegiance at 8:30am, and the kind of irreplaceable local character that chains can't manufacture.

"The best breakfast and brunch in Annapolis. Always worth the wait."

Iron Rooster does all-day breakfast and brunch that Annapolis locals treat as essential — chicken and waffles, biscuits and gravy with house-made andouille, and cocktails starting at breakfast. The waits on weekends are real.

"The most intact 18th-century colonial streetscape in America."

Annapolis has more 18th-century buildings than any other city in America — the Maryland State House (1779, oldest state capitol in continuous use), the William Paca House, and block after block of colonial brick townhouses on cobbled streets.

"The sailing capital of America. Learn here."

Annapolis has more sailboats per capita than any other US city — the Bay is ideal for learning and sailing. The Chesapeake Bay Sailing School and several other schools offer lessons from beginner to offshore certification.

"The Bay Bridge launch point. Swimming and summer beach."

Sandy Point is where the Bay Bridge crosses — the park has a beautiful swimming beach, boat launches, and excellent views of the Chesapeake at its widest point. The osprey population here is extraordinary in summer.

"Blue crabs are a Maryland religion. Join the church."

From May through October, crabbing is the social sport of the Chesapeake — trot lines from a small boat or crabbing from a pier with chicken necks on string. The Navy MWR often has crabbing events. Local marinas have rental boats.

"Scenic tidal river paddling on the Chesapeake watershed."

The South River and Severn River systems around Annapolis offer excellent kayaking through tidal creeks, past osprey nests, and through the marshes that define the Chesapeake Bay landscape.

"Brigade of Midshipmen. The oldest military tradition in Annapolis."

The Naval Academy's noon formation — the entire Brigade of Midshipmen assembled in Tecumseh Court — happens on weekday mornings during the academic year and is open to base visitors. One of the most impressive military formations you'll see.

"35 miles west. The world's greatest museum city."

The Smithsonian Institution's 17 museums are free. The monuments are extraordinary. The National Archives has the original Constitution and Declaration of Independence. The Kennedy Center has world-class performances.

"Fossils, Chesapeake Bay ecology, and lighthouse tours."

Calvert Marine Museum in Solomons (55 miles south) is one of Maryland's finest — Miocene fossils from the Calvert Cliffs (sharks' teeth washing up on the beach), a complete Chesapeake Bay ecology exhibit, and tours of the Drum Point Lighthouse.