When I turned 21, I used went with Hagerty. At the time they were the only company that would insure drivers under 25. There are some rules though. You have to have a "Daily Driver" that is insured with a "regular use" insurance company (Geico, Allstate, State Farm, etc) for each licensed driver that lives with you, assuming you had a wife or girlfriend. The vehicle has to be in an enclosed locked garage when not in use (it can sit out overnight if you take it on a trip). They don't have a mileage limit like many collector insurance companies do, but they will ask for an estimate and make you justify it. I currently only have my '78 Caprice insured with them, because they told me I can't haul anything in my truck. I didn't want to risk having no insurance if something happened while I hauled something, so the '67 C10 is riding on my regular car insurance
. I don't know if they insure in Canada though.