I'm from Canada and am planning a trip from here all the way down to the bottom of South America. My insurance is kind enough to insure me here, as well as the US. Outside of that, though, they are no help.
They pretty much only have advice for Mexico (buy insurance in the Southern US before you enter) and will at least refund anything I paid while I was down there (if I send in some documentation).
Beyond that though I have no idea how to insure my vehicle. To be clear, many of the countries require that you purchase their insurance when you enter, which you can do at the border. This is relatively cheap and I expect it only covers basic stuff such as third-party liability, or perhaps nothing at all.
It's not going to replace my vehicle if it is stolen and may not help in many other situations. Is anyone aware of any kind of policy that will cover me across various countries? I imagine such a thing would be pretty expensive, but I at least want to see what's out there.