Obviously, some aspect of international law would provide the greatest liklihood of opportunities for international legal travel. Of course most of those opportunities are going to end up being with our largest business and finance partners - in other words primarily first world countries or at least not places like tiny Costa Rica. Trade law may be one good choice. Can you say CAFTA?
Keep in mind that a degree from a prestigious law school is certainly a big advantage, but you are starting late in the game and will be competing against lawyers with many more years of experience in that specialty area. You can't do much about your lack of legal experience except be patient and pay your dues. But you might mitigate that by leveraging on you tech background, by going into some field of law that relates to your existing experience as TMan & Bombero suggested. That degree of specialization will still take many years to develop.
Whatever career path you pursue, some degree of fluency in Spanish would also greatly enhance the likelihod of your getting assignments in Spanish speaking countries. That may be something you already have or could learn, but I'm guessing you are not a native spanish speaker and there are plenty of bi-lingual Hispanics in the US, many with college degrees.
I don't mean to discourage you in your plans, but I don't think it is an easiest course that you have laid out. I agee with Bombero and Astro that finding a career that allows for generous vacation time is a much more likely prospect than finding one that enables you to work in CR (besides you don't want to go to CR to work anyway).
You already have expertise in the tech field. Are you sure there are no prospects in that area. Intel has a big plant in CR. I'm sure there may be other tech companies there. Or you could just hang out your own shingle as Astro suggested and work as a consultant. It doesn't have to be based in CR, but it could be, and your target clientele may or may not be in CR either. The big negative of consulting work is that it is not always steady, but that fits in perfectly with your goals as you could just use the time off for your trips to CR.
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