Political map of North America & the Caribbean 26 December 1492 (First contacts): Finding the first people he encountered (Guanahani) peaceful and friendly, Christopher Columbus sailed southwest to discover and explore the northern coasts of Cuba (which he named ‘Juana’) (History of Cuba) and Hispaniola. In December 1492 his largest ship, the Santa María (Santa María (ship)), ran aground off present day Haiti in Hispaniola, compelling Columbus to establish the 36-man fort of La Navidad there with the help of Guacanagaríx, chief of Marién (Guacanagaríx). He then returned across the Atlantic with his two remaining ships, reaching Spain in March 1493.