The settlement of Spanish America began with Columbus's second voyage. The first voyage had been a successful reconnaissance, carefully planned and ably executed. Making, by good fortune, the best of the North Atlantic wind system, Columbus had sailed from the Canaries to the Bahamas before the north-east trades, and back to the Azores in the zone of the westerly winds of winter. He had discovered the two largest islands of the Antilles, Cuba and Hispaniola. He claimed, and believed until his death, that he had found islands lying off the coast of eastern Asia, and possibly part of the mainland too. We cannot be sure whether these claims agreed with Columbus's original intentions and promises, nor whether Ferdinand and Isabella entirely accepted them—some intelligent contemporaries certainly did not. But beyond doubt Columbus had discovered an extensive archipelago of hitherto unknown islands which yielded some gold and were inhabited by a peaceful and tractable, though extremely primitive, people. Whether these islands were really within striking distance of the settled parts of Asia remained to be seen; but they were certainly worth careful investigation.

The first voyage, though successful, had been expensive. Columbus had lost his flagship and had been compelled to leave half his men behind in Hispaniola to face an uncertain fate. The plunder he had secured was negligible in proportion to the cost of the enterprise. It was now essential to follow up the discovery and to produce a return on the investment.