First thing to know is "where on earth is the Caribbean?".  Well, here's a link to Google Earth which gives you the general layout and geography.  Zoom in and out or plot your current location, distances, and so on.

OK, now that you have an idea of the "where", let's research a little further.  I have never met Tim O'Keefe, but wish I had.  I share his passion for travel, writing and photography.  His website (actually he has many sites) is one of the more informative and comprehensive about the Caribbean Islands with great insights of the pro's and cons of different places.  He has a detailed list of the Islands and a brief summary on each, with links to all of them and more detail if you chose to research further. 

Surf there for a while, but do come back because we need to head out to the Bahama's, one of my favorite destinations.