ASA Sailing Schools in Maryland

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Directory of American Sailing Association sailing schools located in the state of Maryland where you can take beginning to advanced sailing lessons.


Very early in the history of Annapolis Sailing School we realized that the best way to learn to sail was by sailing. All of our instruction, whether introductory or advanced, reflects this commitment to hands on, experience-based learning. Some concepts are best conveyed in a classroom setting, and there is a place for formal theory in any learning program. The “Annapolis Way,” however, blends a minimum of theory with a maximum of hands on experience. … Continue reading Annapolis Sailing School

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BaySail’s teaching philosophy is to ensure that the student gets as much time behind the helm as possible while making certain the experience is fun, educational and above all increases one’s passion for sailing. BaySail classes are taught on our late model fleet of sailboats that are sized to accommodate the recommended boat length for the level of certification attained. In addition, BaySail offers a three day course option for all levels ensuring the student … Continue reading BaySail School and Yacht Charters

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Online Sailing Course

Blown Away Sailing is located in the quaint and historic, eastern shore town of Rock Hall, Maryland. Not only is Haven Harbour Marina home to Blown Away Sailing but it is also a resort destination. In addition to a full array of marine services, Haven Harbour offers lodging at the High Tide Inn and a restaurant and bar is serves up tasty fare on the weekends. A relaxing pool and showers are made available to … Continue reading Blown Away Sailing

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Start your Sailing adventure today with Cruise Annapolis Sailing School, located in the Historic maritime district of Annapolis, MD on the Chesapeake Bay. You will sail past Americas Sailing Capitol favorite landmarks in the Severn River including the US Naval Academy, historic Thomas Point Lighthouse, and under the Chesapeake Bay Bridge during your training.

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Delmarva Sailing School operates on the Chesapeake Bay from May-October. We run as Virgin Islands Sailing Academy in Saint Thomas, US Virgin Islands from December-April, with the same great sailboat and instructors. We also teach Ocean Passage Making, as we move our teaching vessel in between the Chesapeake Bay and Saint Thomas.

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Arabella Sailing Vacation
School-Maryland School-MD-Featured

At the Maryland School of Sailing and Seamanship, helping people become exceptional sailors is our passion. That’s why our reputation as a serious school for serious sailors follows our students wherever they go. We don’t cut corners or compromise safety to sell certifications. We simply offer the best sailing instruction and turn out the finest sailors found anywhere. Since 1991, we’ve completed more than 240 long distance ocean training cruises and are known worldwide for … Continue reading Maryland School of Sailing

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School-RR Charters And Sail-MD-Featured

We own three boats, a Cal 22, a Hunter 28, and a new Beneteau Oceanis 41 for our 104 and 106 classes. Our beginning courses are taught over three days in the peaceful Chester River just off the Chesapeake Bay. For our 104 class we explore the calm rural anchorage areas of the Eastern Shore and visit Annapolis. Our 106 class does a Delmarva circumnavigation of approximately 450-500 nm with lots of night and ocean sailing experience.

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Sail Solomons Solomons, Maryland

(410) 326-4917

School-Solomons-MD-Keelboat Grads

Our racing and cruising and chartering experience enables us to target the training to our student’s particular requirements. We truly love our jobs, but we take our sailing seriously so you will be safe on the water.

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Online Sailing Course
School-SailTime Annapolis Sailing Academy-MD-Featured

SailTime Annapolis is proud to offer our sailing school services to both members and non-members of SailTime Annapolis. We are located in the Port Annapolis Marina and sail in front of Annapolis harbour. At SailTime Annapolis you will find experienced, professional teachers, new yachts, and the flexibility to work with your busy schedule. Whether you are a first time sailor or an experienced salt, we have a course that will cater to your needs as … Continue reading SailTime Annapolis Sailing Academy

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The Sailing Academy Tracey's Landing, Maryland

(410) 867-7177


The Sailing Academy, formerly “Capitol Sailboat Club” has been introducing people to sailing for many years. Our teaching method is more like on the water coaching than simply taking a class. The reason for this is simple; we started out as a Sailboat Club, not a school.  Our goal was to coach new sailors to become  proficient and confident so they could take our sailboats out on their own. Even though we have been an … Continue reading The Sailing Academy

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