Take fun and informative sailing classes at Delmarva Sailing School 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.

Since we began operating in 2008 we have taught thousands of people to sail to American Sailing and Captain In You Sailing School high standards. We offer a complete program of both private and group classes that allows students to go from beginner to advanced sailors, under the guidance of caring and knowledgeable instructors, on quality sailboats. No other sailing school on the Chesapeake Bay offers the wide selection of classes or the superior quality of classes offered by Delmarva Sailing School.

It is a simple fact that it takes less time to learn to sail at Delmarva Sailing School. Streamline your sailing education with our internally developed Captain In You Sailing Schools sailing curriculum that has proven effective in helping students quickly learn the information required to gain ASA certification, and cruise safely on their own. Most sailing schools do not have a curriculum for their classes and students are forced to undergo unorganized sailing classes, some over many days, that do not meet student objectives, and cost more. Our students have an average score since 2008 of 99% on ASA on the water skills and 97% in written ASA knowledge testing.

Unlike other schools that provide education in a day sailor program or classroom and return to their home port at the end of the day, our ASA103, ASA104, and higher sailing classes emphasize learning in a real environment, conducted as we move our sailboat to fun destinations on the Chesapeake Bay, including Annapolis, Saint Michaels, Galesville, the Magothy River, the Rhode River, and Solomons Island. All of our instructors are ASA certified sailing instructors and have their US Coast Guard captain’s license, ensuring the finest instruction available.

All of our sailing classes are taught in a 2-7 day, live aboard approach, where students are totally immersed into learning to sail and cruise, and no hotels are required. Class size is kept small and is typically 3-4 students. Classes are available April – November to fit almost anyone’s schedule.

By choosing Delmarva Sailing School for your sailing education you can realize your dream of learning to sail. Our alumni charter sailboats in destinations all over the world, and many have purchased their own sailboat.