Re: sailboat insurance in canada
Offshore insurance can be difficult to get... or at best, very expensive for full coverage. hopefully Killarney Sailor (currently working his way down the South African coast) will check in in a few days and offer some information on that front.
Ask a few marine specialty insurance carriers to see what they need and what they charge. I don't think you need to deal with a Canadian carrier either, nowadays you should be able to shop globally. We have friends winter-cruising the Caribbean each year, they are insured but I think it's with an outfit in the UK. But they're not circumnavigating nor often sailing at night.
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)
1984 Fast/Nicholson 345 "FastForward"