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The United States declares Cuba a State Sponsor of Terrorism. Cuba was removed from the list by the Obama administration in 2015 during the Cuban thaw.
2021-01-11

The Trump administration, through the Department of State and Secretary of State Rex Tillerson, expels 15 Cuban diplomats, after pulling half of its own embassy staff from Havana on Sept. 29, due to the alleged failure of Cuba to take appropriate steps to protect American personnel against the mysterious health attacks.
2017-10-3

The first commercial flight from the United States to Cuba since 1961 takes place as "JetBlue Flight 387" lands in Santa Clara, Villa Clara province, after a 51-minute flight from Fort Lauderdale, Florida. "JetBlue Flight 387" had 150 passengers, including United States Secretary of Transportation Anthony Foxx.
2016-08-31

Carnival Cruise Lines says it will postpone its first cruise in 50 years from the United States to Havana, if Cuba does not waive its rule and allow Cuban-Americans passengers. Current Cuban law does not allow those born on the island to return by sea.
2016-04-18

The United States and Cuba sign an agreement restoring commercial air traffic between the two countries for the first time in 50 years. The U.S. Department of Transportation immediately opened bidding for as many as 110 U.S.-Cuba flights per day to Havana and nine other destinations. Travel from the U.S. is permitted in 12 authorized categories, which does not include tourism.
2016-02-16

The United States and Cuba reach an understanding on restoring regularly scheduled commercial flights. Currently, the only option available is charter flights.
2015-12-16

U.S. and Cuban officials sign an environmental accord in Havana, the first such agreement since the countries renewed diplomatic relations this summer.
2015-11-18

The United States departments of Commerce and Treasury announce removal of a series of restrictions on Americans traveling to and doing business with Cuba effective September 21, 2015. The U.S. economic embargo, itself, remains in place until Congress acts.
2015-09-18

The United States and Cuba officially announce that embassies will be reopened in each other's countries for the first time since 1961.
2015-07-1

Cuba starts releasing political prisoners as part of an historic agreement with the United States announced last month.
2015-01-6