1492 Christopher Columbus's expedition makes landfall in the Caribbean, specifically in The Bahamas. The explorer believes he has reached South Asia
1493 Explorer Christopher Columbus arrives back in Lisbon, Portugal, aboard his ship Niña from his voyage to what is now The Bahamas and other islands in the Caribbean.
1780 The Great Hurricane of 1780 kills 20,000-30,000 in the Caribbean.
1962 Cuban Missile Crisis ends: In response to the Soviet Union agreeing to remove its missiles from Cuba, U.S. President John F. Kennedy ends the quarantine of the Caribbean nation.
1983 Operation Urgent Fury: The United States and its Caribbean allies invade Grenada, six days after Prime Minister Maurice Bishop and several of his supporters are executed in a coup d'état.
1986 Twenty-eight years of one-family rule end in Haiti, when President Jean-Claude Duvalier flees the Caribbean nation.
1995 A Cubana de Aviación Antonov An-24 crashes into the Caribbean off southeast Cuba killing 44 people.
1995 On the Caribbean island of Montserrat, the Soufriere Hills volcano erupts. Over the course of several years, it devastates the island, destroying the capital and forcing most of the population to flee.
2007 A 7.4 magnitude earthquake occurs off the northern coast of Martinique. This affected the Eastern Caribbean as far north as Puerto Rico and as far south as Trinidad.