I think it's as simple as that. Chiles defines himself and his life as a sailor. So, he sails. Just what he does.
You say his latest loop took many years, but it seems from his blog that it took all of about 18 months! That's a lot of sailing, and not much "visiting" when stopping.
Beats making donuts every morning. Probably, anyway. (But perhaps the donut maker wouldn't have his life any other way )