Belize is one of our favorite places in the world. Cheapest Caribbean country or most expensive Central American one - depending on how you view it. No chain properties, but your $$ goes very far and you could easily score award flights there during the summer. Beautiful scenery (and excitement) on the interior near Guatemala, and some of the world's best diving on the islands. Great food, nice people, it's a winner.

If you want to use miles and points, consider St. Martin. Two countries in one and one of the coolest airports (this is FT after all). Plus they have some of the best restaurants in the Caribbean (at least in the winter when French chefs escape to there).

Hawaii is 10 hours from you. Great place, but far from MCO.