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Quest for financial support for a voyage

By about 1484, Columbus proposed his planned voyage to King John II of Portugal. The king submitted Columbus's proposal to his advisors, who rejected it, correctly, on the grounds that Columbus's estimate for a voyage of 2,400 nmi was only a quarter of what it should have been. In 1488, Columbus again appealed to the court of Portugal, and John II again granted him an audience. That meeting also proved unsuccessful, in part because not long afterwards Bartolomeu Dias returned to Portugal with news of his successful rounding of the southern tip of Africa (near the Cape of Good Hope).

Columbus sought an audience with the monarchs Ferdinand II of Aragon and Isabella I of Castile, who had united several kingdoms in the Iberian Peninsula by marrying and now ruled together. On 1 May 1486, permission having been granted, Columbus presented his plans to Queen Isabella, who, in turn, referred it to a committee. The learned men of Spain, like their counterparts in Portugal, replied that Columbus had grossly underestimated the distance to Asia. They pronounced the idea impractical and advised the Catholic Monarchs to pass on the proposed venture. To keep Columbus from taking his ideas elsewhere, and perhaps to keep their options open, the sovereigns gave him an allowance, totaling about 14,000 maravedis for the year, or about the annual salary of a sailor. In May 1489, the queen sent him another 10,000 maravedis, and the same year the monarchs furnished him with a letter ordering all cities and towns under their dominion to provide him food and lodging at no cost.

Columbus also dispatched his brother Bartholomew to the court of Henry VII of England to inquire whether the English crown might sponsor his expedition, but he was captured by pirates en route, and only arrived in early 1491. By that time, Columbus had retreated to La Rábida Friary, where the Spanish crown sent him 20,000 maravedis to buy new clothes and instructions to return to the Spanish court for renewed discussions.