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:

ASA 105-106                                December 7-11

Bahamas Flotilla                          January 16-23 (2016)

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!

Come to the Bahamas with us January 16th-23rd. Information and registration are on our special events page.

 Click Here to see some pictures of last year's trip

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.