European settlements in the Caribbean began with Christopher Columbus. Carrying an elaborate feudal commission that made him perpetual governor of all lands discovered and gave him a percentage of all trade conducted, Columbus set sail in September 1492, determined to find a faster, shorter way to China and Japan. He planned to set up a trading-post empire, modeled after the successful Portuguese venture along the West African coast. His aim was to establish direct commercial relations with the producers of spices and other luxuries of the fabled East, thereby cutting out the Arab middlemen who had monopolized trade since capturing Constantinople in 1453. He also planned to link up with the lost Christians of Abyssinia, who were reputed to have great quantities of gold--a commodity in great demand in Europe. Finally, as a good Christian, Columbus wanted to spread Christianity to new peoples. Columbus, of course, did not find the East. Nevertheless, he called the peoples he met "Indians," and, because he had sailed west, referred to the region he found as the "West Indies."

However, dreams of a trading-post empire collapsed in the face of real Caribbean life. The Indians, although initially hospitable in most cases, simply did not have gold and trade commodities for the European market. In all, Columbus made four voyages of exploration between 1492 and 1502, failing to find great quantities of gold, Christians, or the courts of the fabled khans described by Marco Polo. After 1499, small amounts of tracer gold were discovered on Hispaniola, but by that time local challenges to his governorship were mounting, and his demonstrated lack of administrative skills made matters worse. Even more disappointing, he returned to Spain in 1502 to find that his extensive feudal authority in the New World was rapidly being taken away by his monarchs.

Columbus inadvertently started a small settlement on the north coast of Hispaniola when his flagship, the Santa Maria , wrecked off the Môle St-Nicolas on his first voyage. When he returned a year later, no trace of the settlement appeared--and the former welcome and hospitality of the Indians had changed to suspicion and fear.