Definitely looks hand made. I'm no expert, but I'd be surprised if it is Cuban in origin. It looks more like something you would find at a tourist trap on an indian reservation. Although it may be an island depiction from the huts in the background.
Speaking of which, that indian on the lid is HARD CORE! He's inhaling through the mouth and the nose at the same time! But I wonder what exactly he's doing... that doesn't look like smoking...
EDIT: Did some image searching, and found this:
http://members.virtualtourist.com/m/p/m/31317/
This statue of an indian chief in Cuba bears many similarities to your box. Including the odd method of smoking.