Scotland, England & the Voyage to India:

The year 1788 begins in Macquarie's diary with him chronicling his attempts in Scotland to raise recruits for enlistment in the 77th Regiment of Foot. Afterwards there follows his description of the storm-delayed voyage from Leith (Edinburgh) to Gravesend, and the march to Dover Castle and the taking up of quarters in the regimental barracks. The months of February and March include descriptions of Macquarie's meetings with his fellow officers, and the preparations for the departure for India.

On the 4 April, his vessel the East Indiaman Dublin weighed anchor, and proceeded down the English Channel. Macquarie's diary records the events of shipboard life, as well as the details of his 10-day visit to the Dutch settlements in Simon's Bay and Cape Town at the Cape of Good Hope. The voyage resumes, with descriptions of the passage through the Mozambique Channel and into the Indian Ocean towards the western coast of India. His arrival in Bombay (present-day Mumbai) on 5 August marks the beginning of a long and significant personal association with the Indian subcontinent — one that would last until March 1807.

The remainder of the diary entries in Macquarie's 1788 journal describe some of the strangeness of his new surroundings in India – though, in general, he indicates more how he sought refuge and security in the familiarity of the small British society of Bombay, rather than in exploring the exotic features and culture of western India.