In the high summer of 1618, two strangers stopped along an Edinburgh street. Both men were weary and dirty from their day's journey. One thought it had left his ‘minde attyred with moody, muddy, Moore-ditch melancholy’. They caught the attention of one of Edinburgh's denizens. The melancholy one fixed John Maxwell with a disconcerting stare, drawing him across the street to demand of the man's companion why ‘he lookes so wistly on me?’ Foiled in his first effort to make an acquaintance in the unfamiliar town, the English poet John Taylor had impishly resolved that ‘the next gentleman that I met withall, should be acquaintance whether hee would or no’. Taylor made a good choice in staring down Maxwell:

John Taylor took the title ‘water-poet’ as a play on his trade as a Thames boatman, or waterman. More than fifteen years’ plying the Thames to the Tower and the South Bank theatres paid off in 1614 when Taylor became a ‘King's waterman’. Success in his literary ventures, inspired by contacts with Bankside players and playwrights, at first proved more elusive. A pamphlet exchange with the travel writer Thomas Coryate brought some notoriety, but ‘promoting his image as a “personality” and turning it to financial account’ in the nascent genre of exotic travel narratives finally brought him lasting fame. A journey down the Thames in a boat made from brown paper and kept buoyant with inflated animal bladders, two dangerous passages by sea to the Humber and Avon rivers, and an odyssey to Prague and back provided fruitful material. It was the journey to Scotland recorded in The Pennyless Pilgrimage that was Taylor's first and most successful effort.

After a fortnight in the Borders and lowlands of Scotland in 1598, Fynes Moryson abruptly turned for home. He never returned to the land of his future king, but there were many others like Taylor who were interested to discover the land and its people.