Health care entrepreneur Randall Pittman quickly discovered his 140-foot cruiser, Whirlaway, was better suited for a voyage to the Galapagos than for quick maneuvering. (He has a 90-foot racing boat, Genuine Risk, to console himself.) A 66-footer collided with New York real estate owner Harry Macklowe's 111-foot Unfurled and limped off with a hole in its side.

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