Personally, we have checked a bag with food in it ONCE. And the bag took a couple of days longer to get to SXM than we did. We have a small cooler that we take as carry-on. I personally would never check food again. Your mileage may vary.

Another option, if you want, is you can rent a cooler for $10 a week from Craig at Packlight. He has a medium sized flat top cooler that we often rent. We use it as a table on the beach also.