Looking into the future...

I've been a Texas teacher for fifteen years and plan to finish this school year where I am currently employed. However, I've signed up on TeachAway and am trying to familiarize myself with everything before the big hiring season begins for next year. My heart is on any Caribbean Island; the bigger the need, the happier I will be. (Private school not important. Air conditioning would be great, but not required. I would even love being a house mom at an orphanage while teaching, if that's an option.) My question is: when is the best time to apply for island positions? I notice there are none listed at this time.