The journal of Christopher Columbus indicates that the Native Americans welcomed him everywhere and accepted his small trinkets as gifts. He enlisted the assistance of an indigenous man as a guide. Although this guide assured him that he had indeed landed on an island, Columbus would not concede that he and his navigators may have miscalculated and issued a declaration that Cuba was a continent.

Columbus left Cuba in 1493, but left behind a number of his men with the goal of establishing a colony, and securing access to gold. He returned in 1496.

May 4. Pope Alexander VI issues a series of bulls that assigns a fixed dividing line (known as the Demarcation Line) between the possessions of Spain and Portugal. It runs 100 leagues west of the Cape Verde Isles. The region laying east of this line is to be settled by the Portuguese, and the territory to the west is to belong to Spain. Signed the next year, this Papal Bull gave Spain legal rights to all new lands West of the treaty line.

From Cádiz, Christopher Columbus begins his second voyage to the New World. He brings 17 ships and 1,500 men, including missionaries, soldiers and laborers. There are about one hundred stowaways, as well as agricultural equipment, cattle and seeds. This marks the first attempt of establishing a permanent Spanish colony in the New World. These men land in 1496, and begin work on the first Spanish colony.

When Velázquez first arrived on the Island he brought with him 300 men who were allowed to choose the towns that they wanted to settle, however 100 men were reserved for the establishment of Santiago de Cuba, which would become the capital of the colonial island.

Once the Spanish established dominance on the island, they sought to increase the Spanish presence and control in Cuba by means of the establishment of the Encomienda System. Under this system, portions of the native population would be assigned to Spanish colonists. The Spanish were intended to be “gentle Christian masters who were to instruct [the natives] in the faith and to feed, clothe, and house them, also while training them to do useful work.”

Hatuey’s armed resistance began on the island of Hispaniola [today Haiti and the Dominican Republic] during the age of Columbus, and probably increased after 1502 when a fleet of 30 Spanish ships brought the new Governor Nicolas de Ovando, hundreds of Spanish settlers, and an estimated 100 enslaved Africans to Hispaniola. Spain was continuing its search for gold, and the Africans were brought to do the hard work.

After about a decade of armed resistance in Hispaniola, in 1511 Hatuey and 400 of his followers climbed into canoes and headed to Cuba. His plan was to mobilize his fellow Caribbean islanders against the bearded intruders and their lust for gold, and the slavery, misery, and death it brought.

The Spanish forces, despite being outnumbered, eventually captured Hatuey in early 1512. He was tied to a stake and burned alive in Baracoa. A Franciscan friar asked Hatuey if he would accept Christianity and go to heaven. After asking if the Spanish would be in heaven and being told yes, Hatuey replied that he would rather go to hell to avoid them.

The City's deep harbor made it a hub for trade, shipbuilding, and the export of sugar, tobacco, and enslaved Africans. The city’s economy relied heavily on plantations and the Atlantic slave trade, enriching Spanish elites and Creole merchants. Creole referred to people of Spanish descent born in the Americas, who often held wealth and influence but were excluded from top political positions reserved for those born in Spain. Havana’s social hierarchy included Spanish officials, Creoles, free people of color, and enslaved Africans, reflecting a rigid colonial order.

Havana was also supported by the Spanish goldmines that were stablished by the early colonists. Although Cuba’s mines were less productive than those in Mexico or Peru, they contributed to Spain’s wealth and supplied Havana’s growing economy. As Indigenous populations declined from disease and overwork, enslaved Africans increasingly replaced them, linking the mining economy, plantation labor, and Havana’s rise as a key port in the transatlantic colonial network.

During the colonial period, Cuba's primary mineral output was copper from the El Cobre mine, the first open-pit copper mine in the Americas, which was established in the mid-16th century. While gold was present, the focus was on copper, which was a major source of export revenue for Spain. Some gold was also extracted alongside other minerals in colonial times, and there's evidence of significant pre-colonial mining of both gold and copper by Indigenous peoples. 

These minerals and precious metals contributed to the economic growth and strength of the Island Colony. From the 1560s into the 1700s Spain's Atlantic trade circulated in annual convoys of ships that gathered in Havana before carrying the fruits of Spain's global empire back to the peninsula—precious metals, tobacco, sugar, cochineal, and cacao from the Americas, and textiles, spices, and porcelains from Asia. The return voyages from Spain brought wheat and other foodstuffs, wines and brandies, and European manufactured goods. Spanish merchants monopolized this imperial trade into the 1800s, with the exception of the Crown's concessions to foreign traders to supply the empire with African slaves. Cuba received some 130,000 slaves between 1511 and 1789. Until the late 1700s imperial trade and defense drove economic activity in Havana and its hinterland.

When Spanish colonization began in Cuba in 1511 under Diego Velázquez de Cuéllar, the island’s Indigenous Taíno population resisted fiercely. The Taíno, led by figures such as Hatuey—a cacique (chief) from Hispaniola who had fled Spanish conquest there—organized armed resistance against the invaders. Hatuey’s forces carried out guerrilla-style attacks, burning Spanish settlements and urging other Taíno groups to unite against the colonizers. His famous declaration that he would rather go to hell than share heaven with the Spaniards captured the spirit of Indigenous defiance. Despite his execution in 1512, Hatuey’s resistance became a symbol of Cuban opposition to colonial rule. Across the island, Taíno groups continued to fight and evade Spanish control, retreating into the mountains and remote forests to preserve their autonomy and protect their people from forced labor under the encomienda system.

Following Hatuey’s death, resistance continued in fragmented but persistent forms. Many Taíno communities refused to submit to Spanish authority, destroying crops, fleeing encomiendas, and forming hidden settlements known as palenques in Cuba’s rugged interior. These groups became early models of resistance that later inspired Afro-Indigenous maroon communities. Spanish colonial authorities responded with brutal military campaigns and forced conversions, but the Indigenous struggle slowed the consolidation of Spanish power throughout the 1510s and 1520s

By 1530 Guamá had about fifty warriors and continued to recruit more pacified indios. The rebellion mainly occurred in the extensive forests of the area of Çagua, near Baracoa in the easternmost area of Cuba, but also farther south and west in the Sierra Maestra. hid himself in the most inaccessible places, the most impenetrable fastnesses of the mountains and hills of Baracoa. In these secret places only known by the natives, he put together a defensive force, always maintaining a careful guard to avoid being discovered. Worried by the uprisings of the Indians, Diego Velásquez organized and sent groups of well armed Spaniards to persecute the rebels. Those which were taken were beheaded (with their heads being publicly exhibited) if they were thought to have killed someone; others were enslaved.

These cruel measures did not intimidate Chief Guamá, whose name was already famous. His actions were not only limited to the area of Baracoa but extended to Maisi y Sagua de Tánamo. He was probably connected with the Indian uprisings which took place in various places on the island between 1527-1530. According to the testimony of a captive Indian taken by the Spanish during the rebellion, Guamá was murdered by his brother Oliguama in June of 1532.