People just hate the idea of losing. Any loss, even a small one, is just so terrible to contemplate that they compensate by buying insurance, including totally absurd policies like air travel.
Restless, and in desperate need of adventure, I quit my job at an insurance company to travel west with a couple of guys I smoked pot with, scandalizing my family.
For me, to find a place that doesn't have an organized tour going to it is becoming more and more difficult. A lot of times it involves danger of a political nature - places where the adventure-travel trips can't go because they can't get any liability insurance.