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Chesapeake Bay Waterfront

Known as "America's Sailing Capital," Chesapeake Bay offers a host of recreational opportunities like boating, fishing, kayaking, canoeing, and windsurfing. This historic waterway flows between Maryland and Virginia and then into the Atlantic Ocean and is a vital ecosystem and the largest estuary in the country. The bay produces delicious seafood such as striped bass, crabs, and oysters for which the state is famous. Walk over to City Dock in the historic district and hop on a sightseeing cruise or water taxi on the Bay.


Prices -

cruise prices vary

Hours -

activities from morning until evening


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


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

American Revolution - Battle of the Chesapeake

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.

Sailing on the Chesapeake

Known as "America's Sailing Capital," there are few places along the East Coast that offers 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 offers sailing packages for visitors. A few options include Schooner Woodwind cruises for sunsets or brunch, Watermark Cruises that leaves from the Annapolis Dock, and Arabella which offers evening excursions along the water.

Helpful Links


Driving Direction to Chesapeake Bay
or Historic Inns of Annapolis
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