I'm just clicking around, thinking about different possibilities. Just a very cursory search for now. Looking for things like, ease of entry (travel docs), legal marriage age, extradition, etc.
1. New Orleans to Cuba:
TC could easily qualify, for the one of 12 categories of unrestricted passage (some call it a travel license), to Cuba. That being, for religious purposes, e.g missionary. The trick would be, what 'outbound' travel documentation would they need. Forget about return travel docs... don't think they plan on a return, for now. If they got to Cuba, they could prob go a number of places, as 'excursion side trips'.
2. Florida to Cuba:
Same deal here, except there are a number of 'travel by boat' operations, bound for Cuba. Option, if somehow, it was easier by ferry, and not one of the huge cruise liners.
3. Additional destination, once they are in the Caribbean:
Costa Rica, Dominican Republic - the more typical destinations. Yet there is a massive archipelago, off the coast of Cuba. These names will sound familiar to you: Antigua, British Virgin Islands, Martinique, St. Barts, etc. http://www.caribbeanislands.com
Do you think he is clever enough?
: Is CT clever enough to get them out of the U.S. Let's face it, he thinks he knows more than everyone else. He seems to have been empowered, by the fact that everyone at the school, chose to ignore the numerous times, he clearly crossed the boundaries of Teacher/Student. The list is getting very long. (The latest one: A student related that TC paid ET $20.00 for good behavior. I find that shocking, that he began to establish of 'paying' for a particular behavior. Y'all know where I'm going with that one). I'm feeling, that he has managed to evade LE, by luck and timing. It will empower him for awhile. Hopefully, his ego will cause him to slip up.