Delmarva Sailing School


Please join us for fun sailing classes on the Chesapeake Bay.

Why learn to sail at Delmarva Sailing School?
    We teach and certify our students to American Sailing Association standards.
Delmarva Sailing School is a part of Captain In You Sailing Schools, Inc. and is an American Sailing Association affiliated sailing school.

Since we began operating in 2008 we have taught thousands of people to sail to American Sailing Association and Captain In You Sailing School high standards. We offer a complete program that allows students to go from beginner to advanced sailor under the guidance of caring and knowledgeable instructors on quality sailboats that sail well. We then help those students to transition to chartering sailboats on their own or purchasing their own sailboat. No other sailing school on the Chesapeake Bay offers the wide selection of classes offered by Delmarva Sailing School.

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 – October to fit almost anyone's schedule.

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 sailing classes emphasize learning in a real environment conducted as we move our sailboat to fun destination on the Chesapeake Bay, including Annapolis, Saint Michaels, Galesville, the Magothy River, the Rhode River, 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.

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. Enjoy just the right mix of education and fun that most students are looking for. 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.
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.
Location, Classes and Prices
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Common Questions
Delmarva Charters
Our Teaching Vessel
Practice Sailing Program
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How to Sign up
Click here to read a "Featured School" article written by ASA about Captain In You Sailing Schools, including Delmarva Sailing School.
ASA101 Basic Keelboat Sailing, ASA105 Coastal Navigation, ASA107 Celestial Navigation, ASA119 Marine Weather, and ASA118 Docking make great Christmas presents. After you order we will mail the course materials in a box suitable for wrapping.