Australia rocks, as far as I am concerned it is by far the best place in the world. Warm, safe, unique, the great barrier reef, rain forests, the list goes on. On the downside I dont think many Americans would be willing to go that far since most who live in southern states are used to getting on a 3 hour or less flight to get anywhere.
I think that the only prerequisite for most of us is that the caribbean island has direct international flights either from Europe or Toronto. That way we can avoid touching soil with ‘the land of the free’. Most Islands you have to fly through Miami or Fort Lauderdale so that does reduce the number of opportunities.