Gilbert had not been the first Englishman to be fascinated by the North American continent. Ever since its discovery by John Cabot in 1497 – just five years after Christopher Columbus had made his historic landfall in the Bahamas – a handful of dreamers and adventurers had toyed with the idea of visiting those distant shores across the ocean. A few of Bristol’s more enterprising merchants had launched expeditions in the wake of Cabot’s voyage, hoping to make their fortunes in trade with the ‘savages’. John Thomas, Hugh Elyot and Thomas Assehurst all sailed into the sunset with high hopes, only to return in bitter disappointment. The scantily clad Indians had showed no interest in English woollens and broadcloths – the country’s most important export – and even less desire to truss themselves up in slashed doublets and taffeta bonnets. Nor did they have anything of substance to offer the merchants. Their bows and arrows fetched a reasonable price as collectors’ items; hawks were in some demand among Tudor courtiers, and ‘cattes of the montaign’ – lynx – made fanciful pets for their noble lordships. But a trade based solely on exotica was never going to be profitable and, after five or six years of failure, the Bristol merchants abandoned their enterprise.

In 1517 there had been a brief flurry of enthusiasm when a London bookseller named John Rastell startled his customers by announcing his intention of founding a colony in America. It was an eccentric idea, even by his own standards, yet he was so confident of success that he refused to allow anyone to deflect him from heading off into the sunset. He gathered ‘thirty or forty soldiers’ and bought ‘tools for masons and carpenters’, but his dream of building a dwelling in America was not to be. The mission ended in farce when two captains refused to set sail and Rastell’s expedition got no further than Falmouth harbour. He ended his days lamenting his failure in verse:

O what a thynge had be than
Yf they that be Englysshe men
Myght have be the furst of all
That there shulde have take possessyon
And made furst buyldynge and habytacion
A memory perpetuall.

Most of these early expeditions had suffered from poor leadership, and all had been jeopardised by a lack of resources, but in 1536 – exactly forty years before Sir Humfrey first began toying with his colonial project – an expedition to America was under way that seemed to have overcome both of these hurdles. It was the brainchild of Richard Hore, a wealthy London leather-seller who had grown weary of his endless trading voyages to and from the Canary Islands. To his friends he was ‘a man of goodly stature and of great courage, and given to the studie of cosmographie’, but his business contacts knew a less savoury side to his character. Hore wanted to be rich and was forever dreaming up schemes that combined money-making with adventure.