I am curious about the backstory to this attempted escape more than the foolishness of his hacking that put him in the crosshairs.
Like, where did he get the boat? Was it stolen? Borrowed?
Was it seaworthy? Sail or power? Where did they leave from?
My guess is that they took off and tried crossing the gulf stream during a period when the wind was contrary and got tossed. The wife then tossed her cookies and probably demanded they get rescued.
Knowing how things operate down there, they probably had eyes on them from the moment they left. The only surprise is that they did not show up on the FBI radar until they got picked up and IDd by the cruise ship. There is hella surveilance down there since the 80s to keep an eye on the smugglers. Even a wooden boat with negligible radar signature will still get scooped as that is what the Haitians are ghosting over on.
I doubt they even got spitting distance from Cuba before the gulf stream put them in the wash cycle and started hauling them backwards. If they had arrived, the Cubans would probably have taken a dim view of their arrival. Unless you have money and a specific float plan, they see any boat entering their sheltered bays and harbours as a yankee plot.