Young couple goes on van tour of US, boy comes back with van - no girl

I just don't think Brian is clever enough to successfully flee the country. It is a lot harder than it used to be to not leave any digital footprints. And for the whole "boat to Cuba" thing you would have to already have a lot in place in advance. If you don't already own a boat in south Florida and have friends waiting for you in Cuba, it would be most difficult to buy/rent one without being witnessed, especially now with the media attention. He's just not that smart. Most likely hiding in the woods somewhere.
How hard is it to steal a boat if you don't plan on ever coming back?
How long would it be before a stolen boat was noticed?