If you say that a task was not all plain sailing, you mean that it was not very easy. Pregnancy wasn't all plain sailing and once again there were problems. or yachting Sport or pastime of racing or cruising a sailboat or yacht. A modern yacht (from a Dutch word meaning "ship for chasing") is a sailboat used for racing. In the 17th century Dutch royalty sailed early yachts for pleasure; Charles II brought the sport to England. Organized yacht racing on the Thames began in the mid-18th century. In North America yachting began with the Dutch in New York in the 17th century. The first U.S. yacht clubs were founded in the mid-19th century. Sailboat races are held over two kinds of courses, point-to-point and closed. Yacht racing has been part of the Olympic Games since 1900. The America's Cup is the preeminent prize in yachting