Operation Sail 1992, which marked the 500th anniversary of Christopher Columbus’ Atlantic voyage, was planned as a joint venture with Gran Regata Colon and generated even greater interest from mariners and the public. Setting out on a journey that retraced Columbus’ route in 1493, the fleet, which included pine-and-oak replicas of Columbus’ caravels, sailed from Cadiz to La Gomera, then on to Puerto Rico for a 10-day regatta before making its way to New York.

In addition to tall ships, the regatta included more than 300 modern racing and cruising boats, 200 of which were in a class that required 50 percent of the crew to be under the age of 21. It was the first time that sail training had been extended to contemporary sailing vessels on such a magnitude.