Originally Posted by MountaineerWV
Do some research on insurance. Lots of info here.
Some countries require insurance, some do not. Of the countries that require insurance, some will allow you to purchase it at borders and others do not. Make sure you know which countries you are traveling through fall in that last category! Sometimes you can buy one policy that covers you in multiple countries. My insurance was good for North America, Europe, and the Middle East. There is a policy that covers Argentina, Chile, Uruguay, and maybe a few others.
As for safety of my bike...I always felt that if someone really wanted something, they were going to take it. I opted to take a cheap bike I could easily replace and not take any items that would devastate me if lost/stolen (family heirloom ring or something).
I would park inside the hotel/hostel or in a secure garage. Left all my gear on my bike except my laptop and shower stuff. Only time I had anything stolen was two t-shirts and a pair of shorts I had just washed that I left on my bed in a hostel.
People that had GSs and multi thousand dollar cameras/laptops/gear were paranoid ALL the time. Don't be that person.
Do you, or does anyone, know countries that require insurance AND do NOT permit you to buy it at the border, excepting of course those that I can easily get cover for on a Green Card, like from ADAC? In my travels this year in Western and Eastern Europe and a bit of Asia, I did not come across any that would not let me buy at the border if they were not on my Green Card.