Before Haughton Forrest's emigration to Tasmania in 1876, the artist had met with considerable success as a painter of nautical scenes. Several of his yachting images were purchased by King Edward VII when he was Prince of Wales, and Forrest continued to paint maritime works throughout his time in Australia.
The artist was an enthusiastic yachtsman, and his sailing experience imbues Top Sail Schooner and Racing Yacht with an almost documentary, photographic quality, which succeeds in conveying a sense of excitement as the boats move into the Harbour. However, despite the artist's precision in representing the boats, lighthouse, sea and the sky, the exact location of the scene and the actual boats involved remains a mystery.
During his time in Australia, Forrests' only travels from his home in Hobart, were to Launceston, and it is unlikely that the scene was derived from anything he witnessed there. Instead, Forrest was comfortable using photographs and publised illustrations of scenes of both landscape and maritime as his reference, and it is likely that this image is compiled from a variety of different sources.
According to Paul Hundley, Senior Curator of the USA Gallery at the australian National Maritime Museum, the scene shows a pilot schooner coming out to escort an American barque into local waters. there are two other schooners towards the rear of the painting, which opens the possibility of the boats being involved in a regatta.
Despite portraying the central boats in the scene broadside, it is unlikely that the painting served as a ship portrait, which owuld typically have been commissioned by the ship's owners or captains of the vessel. Nevertheless, Forrest treated the scene, including the nature of the rigging and the movement of the wind through the sails, with a level of skill and attention to detail which equals the demanding requirements of that genre.