Bad news guys
Bad news guys
There I was planning my Cuban vacation for all of fifteen minutes and then I found out Americans are not allowed to go to Cuba for tourism. WHAT THE HELL OBAMA.
But seriously. What a dumb fucking rule. Death to America
You can go. Literally no one cares. Just fly to Miami and get a separate flight to Cuba, the local airline will even give you a tourist visa to fill out mid-flight.
The “ban” is completely superficial to deter tourism agencies and airlines from organizing mass tourism in Cuba, and it’s a declaration by the Department of State that if anything happens that you are on your own and they will not help you with anything should something go wrong.
FREEST COUNTRY IN DA WHORL 
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Some disclaimers:
- Commenting based on what I've read, not what I've done. Though Cuba is definitely a place I want to see.
- I'm assuming "what the hell Obama" wasn't sarcastic. If not, I'm probably going to sound tonedeaf.
- I realize this is a Marxist instance commenting about traveling to a communist country. My values don't align with that, though I suspect they aren't terribly far off. Still, we may have different mindsets, if that comes up.
My disclaimer will probably be longer than the rest of my comment, nonetheless, here we go!
The important part is that, as I understand it, Americans aren't restricted to traveling to Cuba. You can't go without a reason, but that reason can be "Support for the Cuban people". That should be the reason for your visit. And you're restricted from using government owned businesses. But you can go and experience the country.
Re: Obama specifically. The fact that you can even do that much is thanks to Obama . He's responsible for the loosening of travel restrictions.
I think you can just fly through Mexico. I think they staple a visa to your passport instead of stamping it. You should research it. They want your dollars