Pre-Conquest

4000 BC: the first migrants into the region, people of the Lithic culture, cross the Yucatan Passage from Mexico by canoe and inhabit Cuba, Hispaniola (the island on which the modern nations of Haiti and the Dominican Republic are found), as well as Jamaica.)

2000 BC: Archaic culture migrates from the mainland of South America north through the Lesser Antilles and into Puerto Rico and Hispaniola.

800 BC: A ceramic-making people migrate northward from South America through the Lesser Antilles and into the Greater Antilles

400 BC: Late lithic culture populations merge with those of the Ceramic Age cultures.

500 AD: There are Ceramic Age sites on every major Caribbean island.

700 AD: On Hispaniola, eastern and central Cuba, Jamaica, and the Bahamas, new ceramics of the Ostionoid series appear. New types of settlements and sites signal the appearance of ancestral Taino chiefdoms.

1400

1458: The city of Constantinople falls under Muslim control.

1470: Africa experiences a population surplus. African chiefs begin trading surplus people to Europeans initiating the practice of European enslavement of Africans.

1484: Bartolomé de Las Casas is born in Seville, Spain.

1492: Taino Indians live in the West Indies. Westernmost Cuba may be home to the Guanahatabeys.

The Island Caribs, sometimes called the Kalinga, interact with and claim ancestry from mainland Caribs.

1492: Spain expels the Muslims to accomplish their 750+ year goal.

1492: Columbus receives authorization to sail from Spain and financial backing to construct and outfit ships for the voyage.

1492: The Niña, Pinta, and Santa María arrive off modern San Salvador Island.

1492: First contact between Europeans and the Lucaya, native inhabitants of the Bahamas, occurs on the morning of October 12. The Lucaya expect friendly trade with the strangers as extensive pan-Caribbean trading networks had been in place for centuries.

1492: The Santa María runs aground near modern Cape Haitian. Columbus places his first small colony – La Navidad – in the main village of a Taino chief named Guacanacarí.

1492: The New World repays the European invasions with a deadly disease, syphilis, which is contracted by Columbus's sailors.

1493: On the second Columbus voyage Spaniards bring horses, pigs, cattle, goats, oxen and chickens. Large dogs are particularly important to them to make war on rebellious native tribes.

1493: La Navidad is destroyed and the men left there are dead. A second town is established with more than 1000 colonists, animals, and supplies, and christened La Isabela.

1493: Sugar is introduced into the tropical lowlands of the Caribbean basin.

1493: The Franciscan order of mendicant friars arrives in the New World.

1494: With the Treaty of Tordesillas the Pope legitimizes Spain's conquest and control of the New World and divides the world in two. Spain receives sovereignty over the western half of the world and Portugal over eastern Africa and Brazil.

1495: Syphilis spreads throughout Europe.

1496: A Taino man named Guaticabanú is the first to be baptized into the Christian faith.

1497: Vasco de Gama rounds the coast of Africa and reaches India, obtaining two shiploads of spices he returns to Lisbon in 1499.