Wow.
I'm a fairly Nazi-esque parent. I do, in fact, have a keylogger on the computer that they use. It's not to catch them, per se. It is to catch some sick F, pervert so I can track him down and kill them if need be.
Teaching you children the difference between right and wrong and how to choose between the two is the most important thing in their life. The more you try to squeeze, the more slips through the fingers. Rather than be completely controlling tight up to the day they become 18, one has to start letting go, little by little. If you have done your job correctly, your kids will know how to make the right decision.
I'd have to disagree with the boating experience from birth to 5 years old meaning nothing. My family has owned boats all every kind for as long as I can research and I could swim before I could walk or talk. I think that this makes a load of difference.
I would prefer that my daughter try to sail the world, as opposed to, seeing if she could break the local record for number of father's for her illegitimate children, or booting heroin for that matter.
Others may disagree, but having a license and driving a vehicle, unsupervised, is a VERY dangerous responsibility. One can go pretty dar and find lots of trouble in a car with 2-3 hours of free time.
Where I would have exercised my parental powers of VETO, however were the time of year that she chose to leave and the lack of comms.