Moving to a Caribbean School Medical with my dog?

That sounds like the most important stuff, but I just saw your other question about him being a maltese, and I'd strongly urge you to reconsider taking him.  I know it's not what you asked, but as we all know, medical school is demanding, and what is he going to do all day long and during some evenings when you have labs or study groups?  What happens if he gets sick - does this island have state of the art vet services?  

If this was me, I'd find a family member or close friend to either care for him or adopt him outright if that's what it takes.  It just doesn't sound fair to him to be in this type of situation, and so much can go wrong.  What if he reacts badly to the water, for example?

you are going to the caribbean not another planet. you can get all that there is needed for your dog. the only difference will be the climate and proberly the cost of the items you are looking for.

what island are you going to by the way

TAKE SOME FOODS

You can purchase food for him down there.  Unless he is on a special diet (Hills c/d,k/d or RC renal, urinary, etc) I would suggest bringing enough food for a month, and when you get there find food and slowly transition him from the food you brought to the food that they have. (Doing so right away can cause diarrhea).  If your dog is on a special diet I would suggest taking him to the vet and explaining th situation and get your prescription renewed, and then make arraignments with your mom, dad, aunt, uncle, or a close friend to ship it down to you on a monthly or as needed basis.  With the price of things these days to bring things on a plane it could get expensive, and dog food can also expire.   As far as your Heartgard and Frontline (or whichever flea preventative you use), I would also suggest purchasing a years worth of  each.  You can also take his bed (if he has one), and a few of his favorite toys to make the move easier.

Hope this helps and good luck.