Indigenous peoples of the Caribbean
The Classic Taíno lived in eastern Cuba, Hispaniola, and Puerto Rico. They spoke a dialect called Classic Taíno. Compared to their neighbors, the Classic Taíno had substantially developed agricultural societies. Puerto Rico was divided into twenty chiefdoms which were organized into one united kingdom or confederation, Borinquen. Hispaniola was divided into roughly 45 chiefdoms, which were organized into five kingdoms under the leadership of the chief of each area's premier chiefdom. Beginning around 1450, Classic Taíno from Hispaniola began migrating to eastern Cuba; they are conventionally known as the Cuban Taíno. The Cuban Taíno gained power over some of Cuba's earlier Western Taíno inhabitants, the Ciboney, but no regional or island-wide political structure had developed on the island at the time of Spanish colonization of the Americas.
Spanish colonization of the Americas
Columbus made four voyages to the West Indies as the monarchs granted Columbus the governorship of the new territories, and financed more of his trans-Atlantic journeys. He founded La Navidad on the island later named Hispaniola (now divided into Haiti and the Dominican Republic), in what is the present-day Haiti on his first voyage. After its destruction by the indigenous Taino people, the town of Isabella was begun in 1493, on his second voyage. In 1496 his brother, Bartholomew, founded Santo Domingo. By 1500, despite a high death rate, there were between 300 and 1000 Spanish settled in the area. The local Taíno people continued to resist, refusing to plant crops and abandoning their Spanish-occupied villages. The first mainland explorations were followed by a phase of inland expeditions and conquest. In 1500 the city of Nueva Cádiz was founded on the island of Cubagua, Venezuela, followed by the founding of Santa Cruz by Alonso de Ojeda in present-day Guajira peninsula. Cumaná in Venezuela was the first permanent settlement founded by Europeans in the mainland Americas, in 1501 by Franciscan friars, but due to successful attacks by the indigenous people, it had to be refounded several times, until Diego Hernández de Serpa's foundation in 1569. The Spanish founded San Sebastian de Uraba in 1509 but abandoned it within the year. There is indirect evidence that the first permanent Spanish mainland settlement established in the Americas was Santa María la Antigua del Darién.