Best Places to Sail the Chesapeake Bay

Annapolis, Maryland

Known as the "Sailing Capital of the United States," Annapolis offers a picturesque harbor, historic charm, and a vibrant sailing community.

St. Michaels, Maryland

This charming town has beautiful seaside views and a historic maritime museum. Sailing around St Michaels offers a mix of beautiful bays and open water.

Solomons Island, Maryland

Located at the confluence of the Patuxent River and the Chesapeake Bay, Solomons Island is a popular destination with calm waters and many anchorages.

Oxford, Maryland

Oxford offers a glimpse into traditional Chesapeake Bay life with its beautiful harbor and historic buildings.

Rock Hall, Maryland

Situated on the Eastern Shore, Rock Hall is a quaint town with great marinas and access to the open waters of the Chesapeake Bay.

Chestertown, Maryland

This historic town on the Chester River offers a mix of sailing experiences, from leisurely river cruises to more open-water adventures on the bay.

Cape Charles, Virginia

Located on the southern tip of Virginia's Eastern Shore, Cape Charles offers a quieter sailing experience with beautiful sunsets over the bay.

Deltaville, Virginia

Known as the "Boating Capital of the Chesapeake," Deltaville offers numerous marine, protected anchorages, and easy access to fishing and cruising spots.

Baltimore, Maryland

Sailing around Baltimore's Inner Harbor offers a unique urban sailing experience, including views of iconic landmarks like the National Aquarium and Fort McHenry.

Norfolk, Virginia

Located at the southern end of the Chesapeake Bay, Norfolk offers diverse sailing opportunities from exploring the bay to venturing into the Atlantic Ocean.

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