In 1806 he went to Jamaica, first managing some estates, and afterwards joining a business firm in Kingston. The latter post necessitated his making frequent journeys, on the incidents of which he based his best known book, Tom Cringle's Log.
In 1822 he left Jamaica and settled in Glasgow, where he engaged in business. Tom Cringle's Log began to appear serially in Blackwood's Magazine in 1829. Scott’s second story, The Cruise of the Midge, was also first published serially in Blackwood's in 1834–1835. The first appearance in book-form of each story was in Paris in 1834. Both stories - "interesting autobiographical portraits of jamaica in the 1820s, written by a perceptive and sympathetic, but transient observer" - were originally published anonymously, and their authorship was not known till after Scott's death at Glasgow.