TOP 30 Chesapeake bay boat shares in Annapolis, Maryland

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Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.

R&R Charters and Sail School, located in Chester, Maryland, United States, is a professional institution dedicated to sharing the joy of sailing with students. Our experienced educators provide personalized instruction to help students master the knowledge and skills needed to feel confident on the water. Whether you prefer individual instruction or learning in a small group setting with friends and family, our maximum of four students per boat ensures that each student receives ample hands-on experience. Captain Penny encourages students to "Learn to sail; you might want to go somewhere."