Chesapeake Windsail Cruises
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Chesapeake Windsail Cruises is a beautiful way to enjoy all the splendors of the waters of the Chesapeake Bay, the Cliffs of Calvert or the beautiful environment of the region, all during a wonderful 2 hour cruise on the Chesapeake Bay. Chesapeake Windsail Cruises sails out of the beautiful Rod 'n' Reel Resort 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.

We hope you enjoy browsing our website and find a lot of useful information for your cruise.
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The idea to provide daily cruises for the tourists and the local community in Calvert County, Maryland was the brainchild 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 currently offers daily sailing cruises out of the Rod 'n' Reel Resort located in Chesapeake Beach, Maryland.
We offer 2 hour cruises on the Chesapeake Bay aboard U. S. Coast Guard examined Eternal Hope, a 42' sailing yacht.
Food menus are available from the Rod 'n' Reel and can be served aboard the boat before departure or delivered to the boat to be served once your cruise is under sail.
Our cruises are scheduled* to set sail at 9 am, 12:00 pm, 3:00 pm, and 6:00 pm, Tuesday - Sunday starting in mid-May and ending the first week in October.
Your two and a half hour cruise, aboard the 42' sailing yacht Eternal Hope, sails out into the Chesapeake Bay, where you will see the historic Cliffs of Calvert and if you are lucky you will see dolphins, ospreys and other amazing habitats or cruise ships in the shipping channel.
If there is a strong breeze out of the west, we may sail close to the other side of the bay!
It has been said ".that the only problem with the bay is that it is so darn beautiful!"
Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay.
You are only a few clicks away from a wonderful stroll in the beautiful bay side towns of North Beach and Chesapeake Beach, Maryland; known as the twin beaches!.
See where famous entertainers and a well known retail store got their start.
Learn how people traveled here from Baltimore and Washington by ferry and train.
These walks are also a great way to see the bay from the shore!
The historic tour will include a stroll on the boardwalk, the pier where many famous entertainers were discovered, and continue throughout the bayside town as historic points of interests are shown.
Chesapeake Windsail Cruises is devoted to delivering a higher passenger sailing experience, a key part of our commitment to refined cruising.
Passengers can expect great hospitality, exceptional seamanship, world class yachts and an elegant and welcoming ambiance with the goal of creating lasting and cherished memories.
You can help!
We are seeking to hire Full & Part-time USCG licensed captains with a sailing endorsement and experience on the Chesapeake Bay.
The ideal candidate must have mechanical & maintenance experience, good communication skills, knowledge of the Chesapeake Bay.
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