Marjorie Wilson, with a cigarette between two fingers, holds the captain's wheel of the "Skylark" sailboat with her fiancé (at the time), Hugh Willoughby III, at her side. According to The Stuart News, Hugh Willoughby III sailed on the "Skylark" from Port Sewall to Jacksonville around May of 1935. Willoughby then boarded a train to work at a ranch in Montana.