Delmarva Sailing School is a part of Captain In You Sailing Schools, Inc., an American Sailing Association-affiliated sailing school. Delmarva Sailing School is the premier sailing school on the Chesapeake Bay. Enjoy the right mix of education and fun that most students seek when learning to sail. Although our classes emphasize educational content, you will likely find yourself in a fun location with time to explore and kick back when the day is done.

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

Streamline your sailing education with our internally developed ASA Sailing Class Study Guides. These guides have 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 ASA Sailing Class Study Guides, and students are forced to undergo unorganized sailing classes that often do not meet student objectives.

Sailing Schools should be evaluated by what and how much students learn. Since 2008, our students have had an average score of 99% on ASA on-the-water skills and 97% in written ASA knowledge testing. ASA has selected our instructors for their highest award, the designation of “Outstanding Instructor,” in 2009, 2012, 2018, 2020, and 2021.

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 our instructors are ASA-certified sailing instructors with their US Coast Guard captain’s license, ensuring the finest instruction.

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

Delmarva Sailing School is home to ASA Instructor Qualification Clinics, which allow our students to become sailing instructors at the most advanced ASA levels.

Suppose students take some time away from sailing and need a refresher. In that case, we also offer unique “Practice Sailing Programs” that allow students to retake Private or Group classes to gain additional practice at the helm at a fraction of the cost (50% off). Please visit the Practice Sail Programs page to learn more.

We also allow our students to charter our sailboats via our sister company, Delmarva Charters, which offers discounted rates for alums. All Delmarva Sailing School students qualify for 10% off Sailboat Charters at Delmarva Charters. Please visit the Class Price Schedule Shop Page for a coupon code for 10% off.

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