The maiden voyage of the Anna, Irving's first captaincy, began propitiously. As he sailed from Liverpool on 3 May 1789, he wrote to his wife Mary informing her of the good progress made by the ship. He commented on the ‘fine promising Wind’ which was ‘so exceeding favourable the Vessel runs out very fast’. The tone of the letter is calm and reassuring and was intended no doubt to relieve the anxieties that his wife, two months pregnant at the time, felt about the voyage. He urged her not to ‘fret and distress yourself without cause’, but to trust in Providence who ‘is able and willing to support you in every situation in life’. The demands placed upon Irving in his new position as captain, particularly on the first day of the venture, probably explain the brevity of this letter. It was with some regret that he told his wife that ‘I really cannot find time to say what I have within’, although he did promise that ‘the next I write shall be a very long one’ (Letter 9).

James Irving did not, in fact, have the opportunity to write to his wife again until August 1789. In a letter dated the first of that month from ‘Telling in Barbary’, he informed her that ‘as a dream all our hopes and prospects are vanished. The Anna is wrecked and everything lost’.