"Can I sail to Cuba with NO experience?"
Hmmm, looks like you can...
Missing Hakken family reported to be in Cuba | Tampa Bay Times
Given the astonishing surveillance capabilities the US has over the Florida Straits, it is a bit surprising they could have made it across there, undetected... Lack of communication between various agencies could be a likely explanation, I suppose...
Or, simply too busy keeping tabs on Beyonce and Jay-Z, perhaps? (grin)