She was born in Yaguana, Hispaniola (today the town of Léogane, Haiti). During Bartholomew Columbus's visit to the chiefdom of Jaragua in the southwest of Hispaniola in late 1496, Anacaona and her brother Bohechío appeared as equal negotiators. On that occasion, described by Bartolomé de las Casas in Historia de las Indias, Columbus successfully negotiated for tribute that consisted of food and cotton for the struggling Spanish settlers under his command. The visit is described as having taken place in a friendly atmosphere. Several months later, Columbus arrived with a caravel to collect a part of the tribute. Anacaona and Behechío had sailed briefly aboard the caravel, near today's Port-au-Prince in the Gulf of Gonâve.
Anacaona's high status was probably strengthened by elements of matrilineal descent in the Taíno society, as described by Peter Martyr d'Anghiera. Taíno caciques usually passed inheritance to the eldest children of their sisters. When there were no children of their sisters, they chose amongst those of their brothers, and failing these, they fell back upon their own.
Anacaona had one child, named Higuemota, whose date of death and date of birth are both unknown.
