Homer began Boy in Boat, Gloucester while staying at the lighthouse on Ten Pound Island in the harbor of the fishing town Gloucester, Massachusetts. During his time in Gloucester, the artist frequently depicted local boys playing on boats, fishing, and waiting for their fathers to return from the sea. In this watercolor he began experimenting with scraping, revealing the white of the paper to create highlights in the large rock at right. Furthermore, he was developing his skill in transparent watercolor, which he used to great effect for the reflective surface of the water.