The ILH officially recognized sailing as a sport in the spring of 2003, making it the first interscholastic league in the U.S. to conduct a sanctioned championship in open ocean sailing. The regattas were held in the waters off Magic Island in the double-handed 420 sailboats. The Hawai‘i and Waikiki Yacht Club Sailing Directors and members of their staff were contracted by the ILH to serve as the coaches for all schools.
Over 100 students participated in the inaugural season and included co-ed varsity teams from the Academy of the Pacific, ‘Iolani School, Kamehameha School, Lutheran, Maryknoll, Mid-Pacific Institute, Sacred Hearts Academy, Honolulu Waldorf School and Punahou. The Punahou varsity sailing team won the 2003 ILH Sailing League Championship by over 300 points.