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Cuba has kind of a lot going on. Here's the basic historical context: After breaking free from Spain’s colonial rule, Cuba was under various forms of US military control and US-backed leaders, like dictator Fulgencio Batista, until a popular uprising put Fidel Castro in power. After Castro assumed leadership in 1959 and a failed US-led Bay of Pigs invasion made relations worse, the US imposed a suffocating trade embargo in the island. This embargo severely diminished resources in Cuba (presently, that means everything from food to internet) and further isolated Cubans already facing limitations on their individual freedoms.
Alongside the embargo was a travel ban for Americans, which affected the largest Cuban population outside of Cuba (Cuban-Americans). This ban, unfortunately, paired well with Fidel’s discriminatory "exit visa" requirement, restricting the travel of Cubans who openly criticize the government. Now that Obama officially gave the thumbs up on transitioning the two countries from enemy to frenemy status, there is a palpable frenzy of Americans packing their bags and updating their Instagram to get there before it changes.