I have friends who have taken their business degree (accouting, finance, what have you) and gone to Bermuda to work for a large bank. I know it's not the Caribbean, but it is smack dab in the middle of the Gulf Stream.
So you get the 'tropical' lifestyle, as well as multinational experience. Some of my friends are still there, 20 years later.
job opportunities in Bermuda : Canadians in Bermuda : Travel Tips & Advice
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It's relatively easy for Canadians to work there, I'm sure it the same for United Statians as well.