Take nothing more than a shorty drytop - if that. You get two check in bags - if you HAVE to take your paddle put it in a surfboard bag. You will not need more than one duffel bag of clothes or anything else. You can normally put two peoples clothes into one duffel bag on the way down, leaving the other persons two bags empty and full of duty free liquour on the way back. Leave anything that you do not want stolen in America, nothing of sentimental or real financial value i.e. jewelery.
One of the biggest mistakes of going "Down South" is people pack too much. It's warm weather, and you can wear the same thing day in day out, except boxers of course, you're not there to impress anyone. As long as you smile, wave, and at least try to speak their language the locals will be impressed with you - dirty/smelly clothes and all , unless you're a prick.
Take any t-shirts that you no longer wear to give to the local kids. No mater the size. And stickers. Ecspecially if the stickers or shirts have any thing to do with surfing or kayaking. It's worth going and spending ten bucks on stickers before going. They eat that shit up. IMHO
Have fun, enjoy, be safe!