About Us

The thinking behind Chesapeake Windsail Cruises

The idea to provide daily cruises for the tourists and the local community in Calvert County, Maryland was the brain child of the founder. He realized one summer when friends and family visited their home in the bay area not only did they enjoy the fine food, entertainment and the beauty of the bay from the boardwalk, they also wanted to see the beauty of the Chesapeake Bay from the bay! He felt that providing this service would not only enrich the visitors’ stay in the Twin Beaches area, but would add to the great experiences that one would find when visiting Calvert County, Maryland.

Chesapeake Windsail Cruises sails out of the beautiful Chesapeake Beach Resort & Spa located in the bay-side town of Chesapeake Beach, Maryland, where you can dine before or after your cruise at the Rod ‘n’ Reel restaurant.

In the villages of Chesapeake Beach and North Beach known collectively as the Twin Beaches there are also other restaurants offering local dishes and cuisines. You can enjoy a stroll on the boardwalks in Chesapeake Beach or North Beach, while visiting antique shops, the farmers’ market, and local shops or stores.

Cruises out of Annapolis and Baltimore, Maryland and Hampton and Norfolk, Virginia are being planned for the future.

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