Now, archaeologists think they've found one of the vessels he used for the journey.
"It is the Mount Everest of shipwrecks for me," underwater explorer Barry Clifford, who discovered the wreck, tells CNN.
Clifford found the wreck in the exact area where Columbus claimed the Santa Maria sank over 500 years ago after running aground. (Specifically, a coral reef off Haiti's northern coast, 10-15 feet under the water's surface.)
Aside from matching Columbus's location, the ship has the right dimensions, and stones found at the site resemble others from the part of Spain where the ship was built.
Indiana University archaeologist Charles Beeker tells CNN that Clifford has "very compelling evidence." Beeker spent several hours underwater at the site, and studied Clifford's documentation, concluding that "Barry may have finally discovered the 1492 Santa Maria."
Clifford says most of the ship is in good shape and he intends to excavate it with the help of the Haitian government. He plans to return to Haiti next month to meet with authorities and map out his next steps.
It's no Bigfoot, but we'll take it.