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.

Hands-on ASA sailing certifications aboard a modern catamaran, small classes, expert instructors, Chesapeake Bay training, and real-world cruising skills in scenic St. Michaels.

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.

Take fun and informative sailing classes and enjoy just the right mix of education and fun that most students are looking for when learning to sail. Although our classes emphasize educational content, when the day is done you will likely find yourself in a fun location with time to explore and kick back.

We provide courses to bring the first-timer to a level of competent seamanship, offer advanced courses for the experienced sailor, and open the world of possibilities for those wishing to charter in the world’s finest sailing destinations

Chronic Sailing is a premier Annapolis-based sailing school, charter company and yacht management services, specializing in catamaran sailing, cruising, and passage-making.

Your adventure starts here! The Sailing Academy is the closest sailing school on the Chesapeake Bay to the Washington, D.C., Beltway, blending prime conditions with easy access. Family owned and operated; our teaching method is closer to on-the-water coaching rather than simply taking a class. Our goal is to equip learners with both proficiency and confidence so they can achieve their own sailing dreams—whether that is to cruise the Chesapeake Bay or to eventually cross oceans. 

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.

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.

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 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 yacht or charter boat.

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.

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.

BaySail School of Sailing is a family-owned and operated ASA-certified sailing school located in the charming waterfront town of Havre de Grace, Maryland—where the Susquehanna River meets the Chesapeake Bay. Our unique location offers the perfect blend of protected inland waters and wide-open Bay conditions, ideal for students of all skill levels.