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

Fall is beautiful on the Chesapeake!

Upcoming events:

Sailing Basics                   Oct. 3-4
ASA 103/104                    Sept. 28-Oct. 2

Annapolis Sailboat Show   Oct. 8-12

Bahamas Flotilla               January 16-23 (2016)

Brush up on your sailing skills in the fresh fall breezes of the Chesapeake Bay

Fractional Sailing      Join The Club!

Sail all season on our yachts for one low fee. Our club is a great alternative to purchasing your own boat.

Check out our boats  

Members may sign out a boat by clicking here. 

Bahamas Flotilla!

We had a fantastic time in the Bahamas in January and February of 2015. Click Here to see some pictures of our adventures.

Located just 20 minutes from the Washington D.C. Beltway at beautiful Herrington Harbour North Marina, on the Chesapeake Bay. We are about 20 minutes from Annapolis, 10 min. from Chesapeake Beach and approximately 45 min. from Northern Virginia.



 Contact_Us        See Course Descriptions

The Sailing Academy

Phone (410) 867-7177

Fax (410) 510-1125

411 Deale Road

Tracy's Landing, MD 20779


Copyright 2013: The Sailing Academy, Inc.

Learn to sail near Annapolis, our sailing school is mid chesapeake bay on the western shore. We offer fractional sailing, sailing classes, courses, charters, seminars and special clinics. Easily accessible from northern virginia, washington dc, calvert county, central and southern Maryland. We also offer youth sailing camps.