Delmarva Sailing School


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

We teach and certify our students to American Sailing Association and our own high standards. Our instructors have been selected by ASA for their highest award, the designation of "Outstanding Instructor" in 2009, 2012, 2018, 2020, and 2021.
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. 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 Association 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 that sail well. 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.

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 that do not meet student objectives. Sailing Schools should be evaluated by what and how much students learn. Our students have an average score since 2008 of 99% on ASA on the water skills and 97% in written ASA knowledge testing. Our instructors have been selected by ASA 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 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.

Delmarva Sailing School is home of ASA Instructor Qualification Clinics allowing our students to go on to become sailing instructors up to the most advanced ASA levels.

If students take some time away from sailing and need a refresher, we also offer unique “Practice Sailing Programs” that allows students to retake Private or Group classes in order 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 with discounted rates for alumni. Please visit Delmarva to learn more.
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.
Group Sailing Class Descriptions and Prices
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Common Questions
Delmarva Charters
Our Teaching Vessels
Practice Sail Programs
Group Sailing Class Schedule
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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.
Private Sailing Class Descriptions and Prices
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Corporate Team Building Program
ASA Challenge Program
How to Become an ASA Sailing Instructor
Additional 10% off all on the water Sailing Classes. Limited Time Only. Sale ends July 31, 2024.

Why learn to sail at Delmarva Sailing School?

Delmarva Sailing School
Rock Hall, MD on Eastern Shore