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.I think its wiser. Ports and airports are choke points. There is no accountability for the conduct of security at airports and naval crew are clueless about maritime law. Plus no matter the size of your wallet you can afford more vehicles leading and lagging you, better security, etc.
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).