Struggles
If you dont have a pilot license from your nation, then its somewhat difficult. With Bermudan citizenship and a Canadian license you would have to work for a Canadian registered outfit in the Caribbean, which are next to non exsistent.
Most operations are of their respected nations or US based. The US based companies require FAA certified pilots and Part 135 or part 121 flight hour requirements and in most cases a US work authorisation (1500 hours total + other hours requirements).
The other operations of their respected nations also parrallel the FAA system which must also meet ICAO standards. In other words, your need 1500 flight hours and some places specific type ratings.
Your best chance at working in the Caribbean is to get an instructors' licnese and build flight time in Canada. If your flight school cannot authorise the permit to work in Canada, Then get the Instructor ticket and head to somewhere in the world such as Africa, middle east, china, korea, malaysia, indonesia, india, guyana.
Get those hours and go where your dream tells you.
No airline will even tell you "NO" without close to the required flight time.
Source: myself
I was in the same position a decade ago. Now I am pilot in the Caribbean.
Last edited by RVR400; 24th Apr 2016 at 14:57.
Reason: Adding