A portrait of the 'Fly', 16 guns, in port-broadside view. She is shown heading south in the Downs (off the east coast of Kent) on the starboard tack, flying a pre-1801 Union jack on the end of her bowsprit and the red ensign. She also appears in stern view on the left heading towards an anchored two-decker flying the flag of a vice-admiral of the blue at the fore, a jack and a blue ensign. Another ship under reduced sail is on the far left, with various small craft also in view. Under the 'Fly's' bowsprit can be seen the cliffs of the South Foreland. To the right of her stern is a Deal lugger and, on the shore, Walmer Castle.

The painting is signed "F. Holman 1779", lower left. The received title of the picture, as inscribed on the frame below, is "The Privateer Fly. Mr. Candia owner" but it is not clear why this may be the case, apart from the fact that in the stern view she appears very heavily manned (as was often so with privateers - private warships licensed to attack state enemies for profit). Both the flags and armament are consistent with this being a portrait of the Royal Naval cutter 'Fly' of 1776.