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The Sailing Academy

Closest Sailing School on the Chesapeake Bay from Northern Virginia and Washington D.C.

Anchor Learn to sail today!


  1. PREMIUM LOCATION: We operate out of Herrington Harbour North, a scenic and well-kept area having been named one of the Best Overall Marinas located right on the Chesapeake Bay!  Only 25 min. from the Washington D.C Beltway
  2. NEW BOATS IN THE FLEET: We have added 2 brand new VIKO S26’s that we use for our Sailing Basics and ASA101 Courses.  Come learn to sail on new boats!
  3. AWARD WINNING INSTRUCTORS:  Not only do all of our instructors have over 8+ years of sailing and offshore cruising experience, but a couple of our instructors have awarded ASA’s “Outstanding Instructor” achievement. Learn from some of the best Captains on the Chesapeake Bay and let us help you fulfill your sailing goals.

Gift cards available

Sailing Courses in Tracy's Landing, Maryland

About Us

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The Sailing Academy is the closest sailing school on the Chesapeake Bay to the Washington DC Beltway. Sailing instruction focuses on teaching family and friends to cruise on sailboats. Learn to sail in a fun, friendly atmosphere!

See What Other Sailors Have To Say!

man learning how to sail in Tracy's Landing, MD

The patience and professionalism of the staff was noteworthy. Captain Roger invited us to participate as much as we felt comfortable accommodating for each individual with respect. The training is invaluable!

– Facebook, Angela Wohlfarth

Had a great morning on a Family Sail with Captain Jeff. DH grew up sailing, while I am a newbie and my 7-year-old had never been on a sailboat before. Super patient, and a wonderful time! Highly recommend!

– Facebook, Marybeth Steil
man and woman sailing on Chesapeake Bay

We had the best time learning to sail! It was our first time sailing and feel like we learned so much! We couldn’t have asked for a better experience! We are definitely planning on returning to get certified!

– Facebook, Rebecca Hansen
two men learning how to sail

We had a great experience in Sailing Basics with Captain Mark Schwenk who is very patient, professional, very knowledgable, and super great at reinforcing and practicing techniques. A++ Highly recommend. We plan to return to complete our ASA 101 and other certifications at The Sailing Academy. Many thanks!

– Facebook, Young Central Station

As an ASA instructor who teaches at the Academy I am a little biased, but I find the family nature and easy going instruction that Captain Jeff promotes to be an excellent way to learn all aspects and levels of sailing. Good boats, great Captains and right in the heart of the sailing capital of the world...The Chesapeake Bay.

– Facebook, Mark Schwenk