Delmarva Sailing School & Charters


Delmarva Sailing School & Charters fun sailing classes take place on the Chesapeake Bay.

Why learn to sail at Delmarva Sailing School & Charters?
Learn to be captain of your own sailboat to American Sailing Association standards.
Delmarva Sailing School & Charters is an American Sailing Association affiliated sailing school and a charterer of premier sailboats. We teach and certify our students to ASA standards, and offer the entire series of ASA sailing classes for inland, near coastal, and ocean water, from beginner to advanced level.

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 May – October to fit almost anyone's schedule.

Delmarva Sailing School & Charters sailing classes are all taught in a live aboard approach, where the student is totally immersed into learning how to sail. During classes students typically visit locations like Annapolis, Saint Michaels, Galesville, the Magothy River, the Rhode River, Solomons Island or other destinations as they learn to sail from a patient and competent captain.

All of our instructors are ASA certified sailing instructors and have their US Coast Guard captain’s license, ensuring the finest instruction available.

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 an fun location with time to explore and kick back.

Streamline your sailing education with our internally developed sailing curriculum that has proven effective in helping students quickly learn the information required to gain ASA certification, and cruise safely on their own.

We believe that new sailors should learn to sail on a sailboat that sails well, so all our classes are taught on a Pearson 39’ cruiser/racer or a 42 Alpha Catamaran that allows students to learn what is possible on a sailboat that performs well, and is equipped with the latest in equipment and in superb condition.
Learn from instructors with multiple perspectives. Delmarva Sailing School is part of Captain In You Sailing Schools, Inc. and operates in the Virgin Islands as Virgin Islands Sailing Academy from November through April with the same great sailboat and instructors. We also teach Ocean Passage Making as we move our teaching vessel in the fall and the spring, to and from St. Thomas and the Chesapeake Bay, with a stop in Bermuda both ways. Captain In You Sailing Schools, Inc. also operate Nockamixon Sailing School on a lake near Philadelphia giving us knowledge of smaller sailboats and lake sailing.

By choosing Virgin Islands Sailing Academy 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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Captain In You Sailing Schools, Inc.
Common Questions
Our Teaching Vessel
Practice Sailing
Schedule and How to Sign up
Video was created by a student and shows what you will learn.