Robert Indiana kept a series of illustrated journals during the late 1950s and 1960s, in which he discusses the development of his work as well as his daily life on Coenties Slip.

This journal page covers August 3–4, 1963. In his entry for August 3, Indiana notes that artist Gerald Laing, his studio assistant, was working on his own downstairs. He writes that he was not willing for the beginning of Red Sails to be seen, but that the work "will find itself finished, as it is an August painting and [very] much in remembrance of Carmen [his mother], before [the] 'Mother' and 'Father' paintings are done."

Indiana also records having dinner in, and that J's (his former partner, fashion designer John Kloss) apartment was featured in a half page article in the Herald Tribune. Indiana frequently referenced current events in his journals, and here he mentions the suicide of Dr, Stephen Ward, a central figure in the Profumo affair, a British political scandal which brought about the resignation of John Profumo, the Secretary of State for War.

In his entry for August 4, Indiana writes that Kloss called, asking if he had seen the article on his "Pop pad," and that he in turn called Art (Arthur Carr, clinical psychologist and art collector) to tell him about it. This resulted in Carr coming down to visit, and the two of them dining at the D/H (doghouse, a term used to refer to the Seamen's Church Institute). Indiana records that upon returning home he went back to work on Red Sails, pretty much finishing its first coat but not painting the letters.