‘Guardian’ is depicted centrally in port-quarter view, flying a blue ensign and a common pennant at her maintop, sailing south-west under easy sail on a north-west breeze in calm sea, past what is presumably intended as the South Foreland Lighthouse. Numerous smaller craft to her left lead the eye towards a setting sun on the horizon. In the background to the right a white cliff coastline with two lighthouses has been simply drawn. Near the cliffs another ship is under sail, with two cutters to the left and further vessels beyond. The land at far left may be intended as the exposed banks of the Goodwin Sands at low tide. The ‘Guardian’ was a former two-decked 44-gun ship loaded with stores in 1789 to be taken to Arthur Phillip’s new colony at Botany Bay (in fact at Port Jackson, modern Sydney). In addition to these stores, consisting of seeds, plants, farm machinery and livestock with a total value of some £70,000, she was also to transport a number of convicts and their overseers. She was commissioned under Lieutenant Edward Riou in April, fitted out at Woolwich until June, and eventually sailed from Spithead for Botany Bay in September, with Riou as commander. This picture thus records the start of her journey, through the Channel to the Solent, at some point in the summer of 1789. In late December, after leaving Cape Town, she hit an iceberg in the Indian Ocean, losing her rudder and part of her keel. Half the crew abandoned ship and were lost: Riou kept control of the remainder and by brilliant seamanship got back to the Cape, where the ship was beached and lost, although most of her stores were saved and later sent on to Australia. Riou himself was killed in 1801, when a captain, commanding Nelson's frigates at Copenhagen. Recent research has established that Toddy was a Greenwich Pensioner, 1783-95, who painted without the use of his hands, bar his left thumb. The John Cleghorn who annotated (and thus supposedly owned) this object has not been conclusively traced, although Greenwich Hospital records a mariner of that name resident in Deptford in the 1810s-20s. He has inscribed the drawing: (1, title) 'Sun Set with View of his Majesty's Ship the Guardian Lieutenant / Rio[u] Commander Going out of the Downs on her way to Botany Bay'; (2, below) 'A London'; (3, lower right and probably later) 'John Cleghorn 1789 / Drawn by Benj. Toddy a Pensioner in Greenwich Hospital - having the Stump of the right Humerus & the thumb only on the left hand'.