I remember a post on Reddit a while back that explained exactly why the embargo was still in place. I'll just paraphrase what I remember.
Quote:
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Florida is a swing state. Many Cuban refugees fled Castro and resettled in Florida. They have a near universal hatred of Castro, but often forget the dictator he replaced was worse. So while a president may see the embargo as a Cold War anachronism, the political reality is doing anything about it would infuriate the Cuban electorate, enough so their party would have little chance of contesting Florida in the next election.
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It's pretty sad that so many people have suffered in Cuba because of the will of so few Americans and their desire for political power. Lifting this embargo is long overdue. Although I will admit as a Canadian tourist it's nice to a place that is American-free.
When I was in Cuba last year the customs person asked me if I wanted my passport stamped since most people don't get it done so that they don't get heckled when they travel to America. But I got the stamp anyways since I like them. And low and behold when I went to California this April I got questioned about my Cuban visit. Why did I go? Who did I see? Do I still have contact with anyone there? All stupid questions and I basically told the customs guy that I don't care about your governments 50 year old cold war embargo. The guy laughed, agreed and sent me on my way. Hopefully this translates to more cashflow for Cuba. It's a beautiful country, but so poor when you step away from the tourist areas.