The NAVY 44 is the latest of three generations of one-design offshore cruiser/racers to be authorized by the Congress for training midshipmen. The end of World War II brought the first fleet of 12 matched 44 foot wooden yawls to the Naval Academy, designed by naval architect Bill Luders. After 25 years of hard service, they were replaced by 12 fiberglass Luders 44 foot yawls; designed with the same exterior lines as the original boats, but with an interior that accommodated an auxiliary engine and a navigation space with chart table. After 25 years of offshore and Chesapeake Bay sailing, these boats were ready for replacement.

The lessons learned in over 40 years of sailing and maintaining these and other boats in the Naval Academy fleet were translated by Captain John Bonds, USN, Commodore of the Naval Academy Sailing Squadron, into specifications for a design competition paid for by the Naval Academy Sailing Advisory Committee (Fales Committee) under the chairmanship of Admiral Charles Larson.

The competition for the designer was won by the firm of McCurdy & Rhodes, Inc. of Cold Spring Harbor, New York. The construction contract was awarded by the Department of the Navy to Tillotson-Pearson, Inc. of Warren, Rhode Island. The first boats were delivered in 1988. Testing of the prototype and subsequent design modifications were carried out by the Fales Committee and Captain Bonds.

The NAVY 44 has proven to be a very successful design, being seaworthy, strong, and stable in the worst weather; fast and comfortable and with the rig and interior arrangement planned to meet the single minded objective of midshipmen training. She is a fitting successor to the famous Luders yawls which gave generations of midshipmen a professional appreciation for wind, wave, weather, command responsibility, and introduced them to the pleasure and excitement of going to sea under sail.