There were many attempts by convicts to escape from the colony by water. A few were successful, many were not.
David Collins gave an account of an escape from Rose Hill (Parramatta) by five desperate men in 1790. At first they were thought to have perished, however four survived. They were found five years later by Captain Broughton when he landed in the Port Stephens district in 1795........
September 1790 - Convicts Escape
In the night of the 26th a desertion of an extraordinary nature took place. Five male convicts conveyed themselves, in a small boat called a punt, from Rose Hill undiscovered. They exchanged the punt, which would have been unfit for their purpose, for a boat, though very small and weak, with a mast and sail, with which they got out of the harbour. On sending to Rose Hill, people were found who could give an account of their intentions and proceedings, and who knew that they purposed steering for Otaheite. They had each taken provisions for one week; their cloaths and bedding; three iron pots, and some other utensils of that nature. They all came out in the last fleet, and took this method of speedily accomplishing their sentences of transportation, which were for the term of their natural lives.
Their names were, John Tarwood, a daring, desperate character, and the principal in the scheme; Joseph Sutton, who was found secreted on board the Neptune and punished; George Lee; George Connoway, and John Watson.
A boat with an officer was sent to search for them in the north-west branch of this harbour, but returned, after several hours search, without discovering the least trace of them. They no doubt pushed directly out upon that ocean which, from the wretched state of the boat wherein they trusted themselves, must have proved their grave
John Tarwood (Turwood) was tried at the Old Bailey in 1787 with others for feloniously assaulting Thomas Holmes, in a certain field and open place, near the king's highway, on the 29th day of May last, and putting him him in corporal fear and danger of his life; and feloniously taking from his person, and against his will, one silver watch, value 40 s. a steel chain, value 6 d. a seal, value 2 d. a man's hat, value 5 s. a guinea, value 21 s. and 18 d. in monies numbered, his property. John Turwood arrived on the Scarborough in 1790.
George Lee and George Connoway were indicted for feloniously stealing, on the 27th day of July last, two live bullocks, value 20 l. the property of Robert Hill. They were found guilty at the Old Bailey in August 1786 and sentenced to death but recommended for mercy. They also arrived on the Scarborough
John Watson was tried at the Old Bailey in 1787 and sentenced to 7 years transportation for grand larceny. He arrived on the Neptune in 1790
There was no man by the name of Joseph Sutton arriving as a prisoner prior to 1802. The Joseph Sutton mentioned by David Collins may have been John Strutton who was tried at the Old Bailey and arrived on the Neptune in 1790 or Joseph Suttle who was tried in Surry and arrived on the Surprise in 1790
D. Collins, An Account of the English Colony in New South Wales, from its First Settlement, in January 1788, to August 1801: with Remarks on the Dispositions, Customs, Manners, Etc of the Native Inhabitants of that Country, London, 1802, vol. II