Christopher Colombus By mabeal Sep 8, 1492 Columbus begins voyage on the Nina, Pinta, and Santa Maria Online Timeline Sep 15, 1492 The ships reach the Canary Islands Oct 12, 1492 The crew spots land Oct 28, 1492 The fleet reaches Cuba Dec 5, 1492 Columbus establishes first Spanish settlement in the New World Jan 16, 1493 Columbus starts return journey to Spain Mar 5, 1493 Columbus arrives in Spain with news of the New World Sep 25, 1493 Columbus makes his second voyage Sep 29, 1494 Columbus returns to Spain again May 30, 1498 Columbus makes his third voyage Aug 24, 1500 Columbus returns to Spain Jan 1, 1502 Columbus makes his final voyage from Spain Nov 7, 1504 Columbus returns to Spain for the final time