Political map of North America & the Caribbean 8 August 1508 (Colonization of Puerto Rico): In 1508 the Spanish explorer Ponce de León led an expedition from Santo Domingo (Captaincy General of Santo Domingo) to colonize the adjacent island of San Juan Bautista (Puerto Rico) (Puerto Rico). Defeating indigenous resistance (Taíno rebellion of 1511), the Spanish secured control over the island during the 1510s. Spain’s longest-lasting New World colony (Spanish Empire), Puerto Rico would remain under Spanish rule until the US occupied it in 1898 (Puerto Rico Campaign).