Talk about whatever, respecting the rules established by Lemmygrad. Failing to comply with the rules will grant you a few warnings, insisting on breaking them will grant you a beautiful shiny banwall.
A community for comrades to chat and talk about whatever doesn't fit other communities
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:
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.