I do not know your experience level, how much you have traveled on a bike or your fitness levels and all of these will play a part in how how your body responds to the stress (mental and physical) of a multiday trip. The stress will ultimatly determine how your sugar level changes and thus needing your attention. I do not think anyone can answer your question but you. If it were me I would start with shorter trips extending them as time goes on to find out how you will respond. Doing them in the lower 48 will allow you access to the proper care if you get into trouble or you get surprised. Traveling remote on multiday trip without knowing how to handle your sugar levels.........is not a good idea...IMHO
Good Luck.......... I am certain Adventure Riding will increase insulin sensativity.