ASA Sailing Schools in Maryland

The Annapolis Naval Sailing Association has been training sailors for over 50 years. Our membership is open to everyone. We believe in maximizing time on the water and emphasize safety in our programs. Continue to sail with us after your first ASA class!

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.

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 sailboats ranging 22 to 38 ft., 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 has ample time at the helm. BaySail has a team of certified instructors, many whom have been awarded by ASA for ‘Outstanding Instructor of the Year’ …

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.

Embark on a transformative sailing journey with The Gratitude Sailing Institute, where expertise meets excellence. As an esteemed American Sailing affiliate, we are committed to setting a higher standard for your sailing education from the moment you step aboard. Join us to experience a program embodying the key elements of successful sailing and seamanship – your personal safety, education, and enjoyment.

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 our advanced program. However, like all pursuits, achieving a standard of excellence requires a thorough mastery of basic skills, and this is what we do …

The Navy Patuxent Sailing Club membership is over two hundred Active Duty, Reserve, Civil Service, and Contractor personnel. We come from all backgrounds with a common interest and a variety of skill levels in sailing. With the Patuxent River and Chesapeake Bay at our back door, we have the finest sailing on the East Coast just minutes away.

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.

Have you completed ASA 101 – 104 and are ready to take on learning to sail a catamaran? We are Sail Away Catamarans, and we specialize in teaching ASA 114 sailing on our beautiful fleet of multihull sailboats.

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.

SailTime Annapolis is proud to offer our sailing school services to both members and non-members of SailTime Annapolis. We are located at Horn Point Harbor Marina at the mouth of Back Creek. 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 a developing captain. Our goal is to teach you the sailing and decision making skills that you need to safely and enjoyable captain your own SailTime …

Starboard Sailing is for those of you who would like that little bit extra in sailing lessons. Our extended, in-depth courses are designed to that higher level of learning. We offer all ASA certifications up to and including Cruising Catamaran and Advanced Coastal Cruising.

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 official American Sailing Association affiliate school since 2002, our instruction was only available to club members. In the spring of 2008, we started offering courses …