I am from Jamaica, it depends on who is choosing, we tend to fall in one of the four categories, Central America, Latin America, Caribbean or North America. The first two tends to cause a lot of trouble, eg: We sometimes get the Latino cable channel feed, the Cheerios box in the supermarket has spanish labeling. Although we were once possessed by the Spanish, since 1665 the English has ruled, therefore making our primary language English. Other countries like Trinidad which is only a few miles from the coast of south America share this same categorization issue. If grouped with Latin America, the language barrier becomes an issue.
I am saying this to say, would Jamaica or even the Caribbean on a whole ever be able to qualify for a Drupalcon North America?. Seeing that big cities out of the US like Toronto have not yet been selected, I doubt this may be anytime soon. But I just wanted to know. We have hosted a KDE conference before, http://dot.kde.org/2008/10/18/join-us-jamaica-next-january-camp-kde and would LOVE to be considered for such an event in the near-to-medium future.
Features: The best coffee in the world - from the source: Blue Mountain Coffee, Best beer in the world: Red Stripe, Sun, Sea, Sand and coconuts.
Awards: 2011 World leading Cruise Destination: http://www.worldtravelawards.com/award-worlds-leading-cruise-destination... along with many other awards.
I am sure there are a lot of other criteria to meet but I'm sure the community would LOVE to spend a few days in a Tropical Paradise :-)

Comments
With all the dcoc excitement
With all the dcoc excitement happening here, its a nice time to get a reply here to change the nood :-)