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In The Area

Chesapeake Bay & Beaches Waterfront

Known as "America's Sailing Capital," Chesapeake Bay & Beaches offers a host of recreational opportunities like boating, fishing, kayaking, canoeing, and windsurfing. This historic water is a vital ecosystem and the largest estuary in the country, flowing from between Maryland and Virginia and then into the Atlantic Ocean.


  • Cruise prices vary


  • Activities from morning until evening


  • Chesapeake Bay & Beaches Blues Festival
  • Antique & Classic Boat Festival
  • Leukemia Cup Regatta


  • Sightseeing cruises
  • Ride the water taxis
  • Sailing, kayaking & boating
  • Explore the maritime history
  • Fishing for famous Maryland seafood
  • Sandy Point State Park


In September of 1781, the British navy encountered French warships who were fighting on the side of American independence. After many strategic maneuvers, the two fleets entered a two-hour exchange of gunfire, and the British suffered a large number of casualties. This epic battle was a turning point in the American Revolution, as news of the defeat of the mighty British navy quickly spread from New York to London.


Known as "America's Sailing Capital," there are few places along the East Coast that offer such extraordinary boating opportunities. With ideal natural harbors and a mild climate, sailing has been a long tradition in Maryland for recreation and fishing.


How Big Is Chesapeake Bay?

This enormous body of water spans over 200 miles between Maryland and Virginia.

Where Can I Go Sailing On The Bay?

There are several marinas easily accessible to visitors where ships launch into Chesapeake Bay and there are several companies that offer sailing packages for visitors. A few options include Schooner Woodwind cruises for sunsets or brunch, Watermark Cruises that leave from the Annapolis Dock, and Arabella which offers evening excursions along the water.