Delmarva Sailing School is a part of Captain In You Sailing Schools, Inc., and is an American Sailing Association-affiliated sailing school. Delmarva Sailing School is the premier sailing school on the Chesapeake Bay and focuses on training cruising sailors. Enjoy the right mix of education and fun that most students seek when learning to sail and cruise. 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 progress from beginner to advanced sailors under the guidance of caring, 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.  Class size is kept small, typically 3-4 students, and classes are available from April to November to fit almost anyone’s schedule.

If you are wondering if Delmarva Sailing School is right for you, all you need to do is consider your goals.  If your goal is to become a cruising sailor on sailboats of 30-50 feet, then Delmarva Sailing School is focused on exactly your goal.  We teach all our classes, from beginner to advanced, on two 39.5-foot sailboats.  Our approach is to teach sailing in a live-aboard style, where every minute you are on the boat, you are learning and experiencing exactly what you need to know to cruise, and no hotels are required.  You will enjoy learning on our two 39-foot air-conditioned sailboats with refrigeration, galley, and many other amenities.  Other sailing schools typically don’t let students live aboard until advanced classes, which may be wasted time and money for those who already know they want to cruise on a 30-50 foot sailboat.

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.  Our ASA101, ASA102, ASA103, ASA104, ASA106, and ASA118 Study Guides are so good that we recommend students use them as their primary learning tools, with the included ASA textbook as a reference to understand them.  Other sailing schools typically have no study guides, so they have to extend their classes over more days to cover the same content.  Sailing Schools should be evaluated by what students learn and how much they learn. Since 2008, our students have had an average score of 99% on ASA on-the-water skills and 96% in written ASA knowledge testing. 

Beginners should start with ASA101 Basic Keelboat Sailing, followed by ASA103 Basic Coastal Cruising, and ASA104 Bareboat Cruising.  All are conducted in a live-aboard style 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.  After you complete ASA104, you can take our ASA106 Advanced Coastal Cruising class and sail a circumnavigation of the entire Delmarva Peninsula (430 miles) and gain experience in nighttime sailing and sailing on the ocean.

All our instructors are ASA-certified sailing instructors with their US Coast Guard captain’s license, ensuring the finest instruction.  ASA has selected our instructors for their highest award, the designation of “Outstanding Instructor,” in 2009, 2012, 2018, 2020, and 2021.

Delmarva Sailing School hosts ASA Instructor Qualification Clinics, which allow those interested to become sailing instructors at the most advanced ASA levels.  Many of the instructors at other sailing schools were certified by Delmarva Sailing School.

If it has been some time since you last sailed and you need a refresher, we also offer unique “Practice Sailing Programs” that allow students to retake sailing 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.

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