Adam:
You state in your letter that you plan to purchase and
register your motorcycle in Ontario. As long as the bike is
registered in Ontario, purchasing insurance for it in Ontario should be very simple. The insurance problems you may have read about elsewhere on this BB all concern people who are trying to obtain insurance in one country, for a motorcycle that is registered in another country.
The fact that you have a Barbados driver's licence does not (directly) affect your ability to purchase insurance in Ontario. There are two different issues you will have to deal with, one is organizing your driver's licence documentation such that you can legally ride the bike in Canada, second is satisfying the insurance company that you are a reasonable risk to insure.
So far as problem number one goes - getting your driver's licence in order - all you need to is to obtain an International Drivers Permit (IDP) in Barbados before you come to Canada. Because Canada is a signatory to the convention that governs IDP's, the combination of your Barbados national driver's licence
and a Barbados issued IDP will be sufficient to make you legal in Ontario. If you establish a residence in Ontario, then you will have to get an Ontario driver's licence, but as long as you are a
bona fide tourist, you will be legal to drive.
Concerning problem number two, getting insurance, any Ontario insurance company can write coverage for your motorcycle, because it is registered in Ontario. The only problem you will face is that you do not have any history of driving in Canada, therefore, the insurance company may charge you a fairly high premium (same as they would charge a new driver in Ontario) for the insurance coverage.
To avoid this, you might want to check ahead of time with the insurance company you presently use in Barbados, to see if they have any association, liason, or common ownership with a Canadian insurance company. If you are presently insured with a large, multinational company - such as
Zurich or
Allianz, etc. (there are many more), perhaps you can get a written introduction to the Canadian branch - this will help you benefit from a lower premium based on your past claim history.
Most Canadian insurance companies have websites - you might want to correspond with them ahead of time, to get an idea about what the insurance will cost.
Finally, be aware that in Canada, the insurance companies normally sell bike insurance only for a whole year. Because our riding season is very short (due to weather), if you try to purchase a policy for just the summer months, they will shaft you - by charging you 20% of the annual price per month for the summer months only.
It is possible that the insurance companies may decline to offer you coverage unless you have completed a motorcycle training course. Such courses are obligatory for new riders in Ontario, before they are able to get a driver's licence for a motorcycle. If this is the case, you can find out more about taking one of these courses (in the Toronto area) by visiting either the
Humber College or
Centennial College websites. The same courses are offered by many other community colleges in other Ontario cities.
Hope this helps you.