January 1, 1959—Fidel Castro overthrows President Fulgencio Batista and establishes a revolutionary socialist state.
1959—Cuba begins nationalizing US-owned properties in Cuba. The US gradually implements trade restrictions. Cuba leans on the Soviet Union to compensate.
March, 1960—President Eisenhower authorizes the CIA to train Cuban refugees to overthrow Castro.
October 19, 1960—The US stops all exports to Cuba.
January 3, 1961—The US breaks official diplomatic relations with Cuba and closes its embassy in Havana.
April 17, 1961—President John F. Kennedy sends 1,500 CIA-trained paramilitary fighters into Cuba to overthrow Castro. The invasion is a categorical failure. Castro uses the victory to reaffirm his control and deepen ties to the Soviet Union.
October 14-28, 1962—The Cuban Missile Crisis. An American spy plane spots Soviet-owned medium to intermediate-range missiles on the ground in Cuba. After weeks of tense negotiations, Nikita Khrushchev agrees to dismantle the weapons.
February 8, 1963—Kennedy prohibits US citizens from traveling to or making financial transactions with Cuba. The embargo devastates the Cuban economy over the course of the next 50 years.
March 19, 1977—President Jimmy Carter allows the US travel restrictions to lapse.
September 1, 1977—Under Carter, the US opens an Interests Section in Havana, technically part of the Swiss embassy. Cuba opens an Interests Section in Washington, DC.
April 19, 1982—President Reagan re-establishes the travel ban and tightens trade sanctions against Cuba.
March 6, 1996—The US Congress passes the Helms-Burton Act, strengthening the embargo against Cuba. The law is condemned nearly unanimously by foreign governments and humanitarian groups.
September 12, 1998—The US arrests five Cubans in Miami, and later convicts them of espionage.
April 13, 2009—President Barack Obama lifts all restrictions on family travel and remittances to Cuba. He eases general travel restrictions, allowing for religious or educational trips to Cuba.
December 3, 2009—Alan Gross, a US government contractor, is arrested in Havana. Gross had allegedly been importing communications equipment and providing it to Cubans. Gross was charged with ”Acts against the Independence and Territorial Integrity of the State” and sentenced to 15 years in prison.
January 14, 2011—Obama further eases restrictions, allowing non-family remittances and US airports to license charter flights to and from Cuba.
December 17, 2014—Cuba releases Alan Gross on humanitarian grounds. The US releases the remaining three of the “Cuban Five” that were still incarcerated. The US and Cuba agree to begin normalizing diplomatic relations again.
May 29, 2015—Cuba is removed from the US State Department’s list of state sponsors of terrorism. Obama had called for the removal days after meeting with Raúl Castro in what was the first meeting of a US President and Cuban head of state in more than 50 years. Cuba had been on the list since 1982.
September 21, 2015 — Pope Francis embarks on a nine day visit to Cuba and the US. Francis had helped broker the warming relations between the nations during 18 months of secret talks.
February 2016—An agreement is signed restoring commercial flight between the US and Cuba.
March 20, 2016—Obama visits Cuba, where he meets with Raúl Castro and becomes the first sitting president to visit the country in 85 years. They hold a joint press conference calling for the trade embargo between the two nations to be lifted.
July 20, 2016—Cuba and America reopen embassies in each other’s capitals. However, the trade embargo remains in place and diplomats are not sent to either embassy.
October 14, 2016—Obama signs a directive easing trade restrictions on Cuban rum and cigars. The use of executive power is viewed as difficult to overturn by future administrations and heralded as one of the strongest steps taken to normalize US and Cuban relations.
This post was updated by Sari Zeidler to include events in 2015 and 2016. Sources: Council on Foreign Relations, PBS, BBC, The New York Times