Re: Real life playing out one of my ideas.
The US has an extradition treaty with every country in the western hemisphere, Cuba included. While politics might delay an extradition, it probably wouldn't stop it - even if they could make it across the Gulf or the Caribbean in a 40 year old, 25 foot sailboat that they have owned less than a month (per the news).
So the best guess is that they have set up a stateside hideout, probably somewhere rural and fairly close by - such as the big bend or panhandle areas of Florida. Another possibility - the drug bust that set this in motion was in Louisiana, so if they can get that far, maybe he has family or buddies in cajun country that will help him hide out.
Seems a fool's game, though, unless they can figure out a way to travel eventually to a country without an extradition treaty with the US (and have some money to spread around).
Other, very unlikely possibilities - find some international non-profit to take up their cause (and fight extradition), or - gulp - decide to go native on some small island in the Caribbean. Based on pix in the Tampa Bay Times, they'll need lots of sunscreen to go that route....
Joe in SPB
Looking for a shoal draft pocket cruiser