What are you a Columbian drug lord driving around in a convoy of Suburban's full of gun toting bodyguards? If so, you're not flying from a "chokepoint" airport, you're not dealing with airport security, and you're not dealing with "naval crews clueless about maritime law", unless you hired same. You fly on your own plane with your own crew from a private airport or travel on your own ship with your own crew, or you charter something much the same. On the other hand, if you're just a wealthier than average person you're still statistically far safer flying than driving, and the chance of you being caught up in something like terrorist activity or other nefarious violence is so vanishingly small that you ought to be far more worried about something like being struck by lightning, which is surprisingly common (around 24,000 people per year are killed by lightning).
Please, I passed drug lord status long ago. I'm way worse than that. The thing is you don't have to be a drug lord. Governments all over the world are much more tolerant of drug lords than they are of skilled political activists or journalists that don't follow the rules. And you get grief every time you go on the water for any substantial distance or time. Having your own boat does not get you past naval stooges. They hate it when you just loiter in the middle of the ocean without going anywhere. They always want on your boat and to stick their nose where it does not belong. Worse, they think because they are on the ocean they do not have to respect any laws. The funny part is they don't even bother to see who it is they are screwing with before they go waving it in your face. On several occasions I've had to take naval and police crew prisoner, board their vessels, raid them for equipment (I don't work for free and fighting fascists is work), and more. They are really cocky and over confident and when they come rolling up on a 40 foot sail boat in a 150 foot patrol boat with lots of soldiers, guns, and a couple gods in tow they think they are going to have some fun stealing your life force and frustrating you or shaking you down for bribes. ONE time I actually got an apology over radio saying they don't want to fight and asking me to leave their waters.
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