In the beginning, all the boats enrolled in the club were steam yachts. However in 1889, the first American Yacht Club sailing race was held. In a "blow", 6 yachts completed a 20 mile course and established a tradition for what was to become one of the preeminent sailing clubs in the world. In the club's fleet have been America's Cup Defenders, Trans-Atlantic and Bermuda Race winners. Its sailors have been Long Island Sound, North American and World Champions in a number of classes. They have captured Olympic medals - most recently in 1996 when Courtenay Becker Dey took a bronze in the Europe class. Four AYC skippers have won the US Women's Sailing Championship.

Through the years, the American Yacht Club Annual Invitational Cruise has been a test of sailing, boats and seamanship, as well as a family competition and plain old fun afloat.