Hughto created his first painting using a sailboat format in 1974. Though the diamond paintings  relied on similar forms, he began to utilize this format in several scales and media in 2016. “Sailboats have been used in painting as a subject and vessels for personality since man traversed water in boats. It is the perfect metaphor for body and soul,” D. Hughto from the interview with DJ Hellerman in the catalog to the exhibition, Darryl Hughto: Diamonds to Sailboats, 2018, Everson Museum of Art.