There was a movement to get Canada to accept a Carribean island a couple of years ago (I want to say it was Turks and Caicos?). Anyway, it would have great vacation implications! I think that the problem was taxation standards and social program issues, but again I'm not too sure.
Here is the link, and it was Turks and Caicos:
http://www.canadiancontent.net/commtr/article_676.html