Choptank River Lighthouse
Beaches & Waterways for Days
Choptank River Lighthouse
You’ll make a splash on this fantastic four-day getaway. Set sail on a historic skipjack, see the sunset from a paddleboard, kayak through grassy wetlands, visit a maritime museum, clamber up to the top of a lighthouse, enjoy local seafood and relax to the lapping sounds of the bay or in oceanside luxury.
Paddleboarding in Spa Creek
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.
Explore nearby eateries:
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
Kayakers at the Blackwater National Wildlife Refuge
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?)
Explore nearby eateries:
Bay Country Bakery - Doughnuts, cinnamon rolls & quiche
Bombay Social - Indian cuisine in a chill atmosphere
Blue Ruin - Regionally themed cocktails & sophisticated mains
Surfboards on Ocean City beach
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.
Explore nearby eateries:
Barn 34 - Jalapeño-popper omelets & Cap’n Crunch French toast
Blue Fish Restaurant & Bar - Sushi, boba & Asian favorites
OCM Crabs - Beachside steamed seafood
SHOPPING SIDE TRIP
From vintage fashions and artisanal jewelry to seaside souvenirs, you’ll find no shortage of shops in Annapolis, Cambridge and Ocean City.
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