In 1887 the prolific Sydney artist Alfred Daplyn exhibited a painting at the annual exhibition of the Royal Art Society of NSW called The Boating Season, Woolloomooloo Bay. It is very likely that this is that painting. It came to the Library untitled but was said to depict the founding members of the Royal Sydney Yacht Squadron. However, these young men — informally posed, fashionably dressed in striped Breton-styled sailing shirts, and well stocked with liquid refreshments — look more like a group of well-to-do friends about to board their boat for a pleasurable sail around the Harbour. The wharf on which the men are sitting is on the east side of Woolloomooloo Bay, with the north shore of the Harbour in the distance.