I recently purchased travel insurance through CAA (of which I have been a long standing member). They do all of the paperwork, and, interestingly, the insurance company that CAA uses is now owned by CAA.
Medipac Travel Insurance is recommended by the Canadian Snowbird Association and the Canadian Legion as a supplier of travel medical insurance for Canadians. I have not used them.
Safety Wing provide medical insurance for digital nomads and expats.
Blue Cross travel insurance is available through its Ontario agent.
You should also look at what, if any, vaccinations you will need, and arrange to get them. The Government of Canada travel website has a list of suggested vaccinations by country. You can also contact your physician or local health unit.
