Build-Your-Own Maryland Adventure Beaches & Waterways for Days DAY 1 | Annapolis Maryland’s capital — and the Sailing Capital of America — is a water lover’s paradise. At Annapolis Maritime Museum & Park , find holographic watermen weaving tales, skipjack sailing tours and aquariums showing what the 17th-century Chesapeake Bay was like. Head outside to admire the water via kayaks and SUPs or take a sunset cruise on the Schooner Woodwind . Stay at the naval-themed Graduate Annapolis to keep seafaring spirits high. Bread and Butter Kitchen Welcoming vibes, scones & pancakes Chick & Ruth’s Landmark known for crab cakes & milkshakes Carrol’s Creek Cafe Fine dining with crab, oysters & waterfront views SHOPPING SIDE TRIPS From vintage fashions and artisanal jewelry to seaside souvenirs, you’ll find no shortage of shops in Annapolis, Cambridge and Ocean City. DAY 2 | Cambridge Listen to your paddle slicing through the water’s surface at Blackwater National Wildlife Refuge . As you navigate your kayak or paddleboard through grassy thickets, watch for bushy-tailed Delmarva fox squirrels, muskrats and a variety of ducks decked out in feathered finery. After, tour the Choptank River Lighthouse and its cozy maritime museum, taking time to soak up some of the best vistas for miles. Spend the night — or a week — at Hyatt Regency Chesapeake Bay Golf Resort, Spa And Marina for obvious reasons. (The name kind of says it all, right?) Bay Country Bakery Doughnuts, cinnamon rolls & quiche Bombay Social Indian cuisine in a chill atmosphere Blue Ruin Regionally themed cocktails & sophisticated mains DAYS 3 & 4 | Ocean City We could write a full book about what to do in Ocean City, but here are some highlights. Explore area history and surfing evolution at the Ocean City Life-Saving Station Museum before parasailing high above the Atlantic’s cresting waves. Spend a full day strolling along the Ocean City Boardwalk . The early-1910s heartbeat of the town is also home to Jolly Roger ’s exhilarating fair rides, a fishing pier, ice-cream parlors, bars, shops and locally loved Fisher’s Popcorn . Stay as close to the water as possible without being in it at Hilton Suites Ocean City Oceanfront Suites . Barn 34 Jalapeño-popper omelets & Cap’n Crunch French toast Blue Fish Restaurant & Bar Sushi, boba & Asian favorites OCM Crabs Beachside steamed seafood Ocean City 90 DESTINATION MARYLAND Ocean City Tourism