Anacaona (c. 1474 – c. 1504) was a Taíno cacica, zemi interpreter, composer, and poet born in Yaguana, Jaragua, Hispaniola (present-day Léogâne, Haiti). After the death of her brother Bohechío [es] in 1500, she became the ruler of Jaragua. In the centuries since her death, she has been re-imagined and memorialized in various forms of poetry, music, and literature from the Dominican Republic, Haiti, and the wider Caribbean.

Prior to becoming cacica, Anacaona was married to a Caonabo, a cacique from the Lucayos (now The Bahamas) who conquered the cacicazgo of Maguana in 1470. However, she spent most of her time in Jaragua with Bohechío. With Christopher Columbus's arrival in Hispaniola in 1492, the Spanish began enslaving Taínos, resulting in conflict. Caonabo, who fought against the Spanish, was ultimately captured and banished in 1496. After Christopher left, his brother Bartholomew took over the administration of Hispaniola in 1496. Anacaona played a prominent role during Bartholomew's visits to Jaragua, welcoming him, helping to facilitate tribute payments to him, and offering him valuable gifts, potentially suggesting her administrative authority and status as a steward of luxury goods.

As cacica, Anacaona initially maintained a policy of cooperation with the Spanish, who continued to mistreat and enslave the Taíno. This led to frequent rebellions, with many enslaved Taíno fleeing to find sanctuary in Jaragua. In 1497, Spanish rebels led by Francisco Roldán also sought refuge in Jaragua among the Taíno. In 1502, Nicolás de Ovando arrived in Hispaniola after being appointed governor, and, after subduing the cacicazgo of Higüey, traveled to Jaragua in 1503. Anacaona welcomed him, gathering the local Taíno to honor him. However, after the Spanish massacre of between 40 and 80 caciques, for which various reasons have been proposed, she was captured and transported to Santo Domingo (present-day Dominican Republic) and executed by the Spanish.

Anacaona was born c. 1474 in Yaguana, Jaragua (present-day Léogâne, Haiti). Her name was derived from the Taíno words ana, meaning flower, and caona, meaning "gold". She was the sister of Bohechío [es], cacique of Jaragua. Anacaona had a reputation as a beautiful, cultured, and kind woman. She was trained in zemi interpretation, for which she was highly respected, and was an acclaimed composer and poet. Her compositions were commonly performed at areítos. None of her writings survive.

Both the Greater Antilles and the Lesser Antilles were historically sites of considerable cultural diversity, but a common distinction is often made between the Taíno people of the Greater Antilles and the Kalinago of the Lesser Antilles. Several Kalinago groups launched military incursions into Hispaniola during the late 15th century, and in 1470, Caonabo, a cacique from the Lucayos (now The Bahamas), conquered the cacicazgo of Maguana, which bordered Jaragua. In response to these Kalinago incursions, many Taíno caciques began pursuing political alliances with each other, and as of 1475, Bohechío was consolidating his own rule in territories to the west of Jaragua. As a result, he arranged a political marriage between Anacaona and Caonabo. The exact nature of their relationship is unknown. Caonabo had many wives, and it is possible that Anacaona was among the highest-ranked of them. It is known that the couple had one daughter: Higuenamota. Anacaona only stayed with Caonabo for short intervals, spending most of her time in Jaragua with Bohechío.

An expedition led by explorer Christopher Columbus first arrived in Hispaniola on 24 December 1492, when his flagship, the Santa María, crashed on the north coast of the island. Guacanagaríx, cacique of Marién, welcomed him and provided the members of the expedition with shelter. Columbus left behind 38 of his men in Marién at a fort called La Navidad. By the time Columbus returned to Hispaniola in 1493, La Navidad had been destroyed. Guacanagaríx gave various accounts of La Navidad's destruction, ultimately claiming that Caonabo had destroyed the fort, possibly as a result of abuses perpetrated against Taíno women and possibly because he resented Guacanagaríx's perceived alliance with the Spanish. Columbus ordered the construction of the town of La Isabela in 1494 and traveled south after hearing rumors that there were gold and settlements there. Conflict arose between the Spanish and the Taíno when the Spanish began enslaving Taínos for forced construction labor. Caonabo fought back against the Spanish, and in 1496, conquistador Alonso de Ojeda was dispatched to capture him. At the Battle of Vega Real, he succeeded, and Caonabo was banished from Hispaniola, dying soon after.

Christopher left the administration of the colony to his brother Bartholomew in 1496. Bartholomew entered Jaragua, where he was welcomed by Anacaona and Bohechío. Historian Maria Isabel Cabrera Bosch speculates that Anacaona held considerable authority over the cacicazgo's administration. Bartholomew demanded tribute, which Bohechío agreed to pay in cassava bread and cotton. In 1497, Bartholomew returned to Jaraugua, where he was again received by Anacona and Bohechío, to collect this tribute. A lavish feast was thrown for him, and the tribute was presented. The Spanish then transported the tribute up the coast, accompanied by Anacaona and Bohechío. At some point along the way, Anacaona stopped at a "little hamlet" that belonged to her. According to historian Bartolomé de las Casas, the hamlet was "full of a thousand things made of cotton, and seats and many vessels and things of service in the house, made of wood, marvelously worked". She gifted many of these items to Bartholomew. Anthropologist Samuel M. Wilson speculates that this may be indicative of women's role as producers and stewards of luxury goods in Taíno society. Las Casas also claims that when the party reached Port-au-Prince Bay, Anacaona, who possessed a large, well-decorated canoe, chose instead to ride in Bartholomew's boat to meet the Spanish ships. Meanwhile, historian Peter Martyr d'Anghiera indicates she had a separate canoe for herself and her followers.

After Bohechío died in 1500 without issue, Anacaona succeeded him as cacica of Jaragua. Martyr claims that after Bohechío's death, Anacona had her brother's "most beautiful" wife buried alive alongside him and was reportedly prevented from burying others in the same manner by a Franciscan friar. This was allegedly a common practice among Taíno at the time. By that point, the territory of Jaragua extended eastward to the Neyba and Ozama Rivers in the modern-day Dominican Republic. While the Spanish continued to mistreat the Taíno, enslaving them to work in Spanish mines, Anacona initially continued Bohechío's policy of cooperating with them. Though, as rebellions against the Spanish grew more frequent, many enslaved Taínos fled to Jaragua seeking safety.