Known as the "Sailing Capital of the United States," Annapolis offers a picturesque harbor, historic charm, and a vibrant sailing community.
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.
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 offers a glimpse into traditional Chesapeake Bay life with its beautiful harbor and historic buildings.
Situated on the Eastern Shore, Rock Hall is a quaint town with great marinas and access to the open waters of the Chesapeake Bay.
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.
Known as the "Boating Capital of the Chesapeake," Deltaville offers numerous marine, protected anchorages, and easy access to fishing and cruising spots.
Sailing around Baltimore's Inner Harbor offers a unique urban sailing experience, including views of iconic landmarks like the National Aquarium and Fort McHenry.
Located at the southern end of the Chesapeake Bay, Norfolk offers diverse sailing opportunities from exploring the bay to venturing into the Atlantic Ocean.