I know this is an old thread, but I wanted to bounce back here about travel. What is everyone's opinion on travelling to Cuba prior to OCS? Is it alright to do so now considering we're normalizing relations with Cuba?
Probably not the best idea, even though we have eased travel restrictions they aren't fully lifted yet and that includes just plain tourism (legally):
http://travel.state.gov/content/passports/english/country/cuba.html
Certianly might be an interesting trip but not worth the hassle of the interest it will garner on security investigations you will have to go through, in my opinion.