Gaspar Corte Real was the third son of the governor of Terceira (an island in the Azores). Gaspar sailed for King Manuel I of Portugal, searching for a Northwest Passage to Asia. He sailed from Lisbon in the summer of 1500, and reached Greenland that year (and did not find a Northwest Passage). He described a land that was green with rich forests.

Gaspar went on a second expedition for the King in 1501, with three ships and his brother Miguel Corte Real. Gaspar sent two of the ships back to Portugal, including the ship captained by his brother. About 50 Native Americans were taken against their will to Portugal. Gaspar sailed southwest from Greenland, and may have reached the coast of Labrador and the Island of Newfoundland.

Gaspar was lost at sea in 1501, and very little is known about his expeditions (much of what is known has been reconstructed by historians). Gaspar's older brother Miguel attempted to find Gaspar in 1502, but was unsuccessful - he never returned from his rescue journey. In 1503, the oldest of the three brothers, Vasco Anes Corte Real, wanted to attempted a rescue, but the King would not allow him to go.