In 25 years I have yet to bother bringing food. But am considering it this year... basics like frozen burgers/brats/steaks and maybe a few premade/frozen casserole-type things. Looking at pickup up a Polar Bear 12 or 24 for this... I'm guessing carry-on is the thing to do with these?

What kind of pain am I in for when I get to C&I at Road Town (taking RT fast ferry this time) if I have a cooler full of food?