Hola:
As a twelve-time Cuba visitor, I can assure you that the Cuban people are not your enemy.
Even people returning from all-inclusive tours have ample opportunity to meet with the locals. They don't have much...but they are proud.
I often meet US citizens in Cuba, they enter through Canada and at point of entry request their American passport not be stamped. No paper trail, no crime.
If you plan to bike independently you will require some Spanish, but I know you will be warmly welcomed.
Allan