"Wind" contains some of the best, most realistic, on deck big-boat sailing sequences ever portrayed. America's Cup skipper Peter Gilmour, whose aggressive sailing during the 1987 defender selection series earned himself a place on the defender boat for the America's Cup, was "Sailing Master" for the film. He was on board for all of the sailing sequences, controlled the boat while they were flying the "Whomper", and can be seen in many of the boat scenes, surreptitiously laying a hand on the opposite wheel. Lisa Blackaller, daughter of America's Cup skipper Tom Blackaller, acted as sailing double for Jennifer Grey for the small boat races in the International 14 class at Newport.