If you're a gear nut you're going to dig this- I give a play-by-play description of what I bring and why. If you're the kind of guy who jams it all into a duffel and sleeps in your board bag you'll be bored to tears. The best part of this whole deal? By the time you see this I'll be 30,000' in the air sinking in to my second beer... enjoy!

1. FCS Leashes: I'm not sponsored by these guys- in fact I pay full retail (well close to full retail- SurfHut, the local surf shop helps me out on equipment) so I've got no bias when I say that these are the BEST stand up leashes that I've used. Check out the yellowing one with the black core, it's survived two trips down to mainland- that's almost a month of continuous (three session a day) use.
That particular leash is battle tested. I've trusted it in double overhead surf where it's been stretched to twice it's length. I've treated it bad, it lives in the open bed of my truck- I just chuck it in the back after each surf. And still, like Old Yeller (pre-rabies) it's never let me down. I've used the others and have reached a verdict: FCS leashes win hands down.
Here's a tip: Buy a new leash before each trip, be sure to switch out your old leash string with new one that comes with your fresh leash- when it gets gnarly, you'll be happy- and so will your board.
2. Patagonia Paddler Trunks: These are basically the only trunks that I own- I've got five pairs of them. If you're like me, meaning you possess a basically square, Torso-Man physique, these are your trunks. They are the most comfortable, durable, best-fitting trunks I've ever had. The inseams are cut a little bit shorter than normal so you don't look like some gangster-vato with your trunks hanging down to mid-shin. The best part is that the trunks have a hanging inner polyester liner (no, it's not a mesh brief-type liner like the shorts you wore in fifth grade) that allows the shorts to slide over your upper leg when your moving around.
Hot tip: Buy the solid black or the dark blue patterned trunks- the dark colors hides guacamole stains, beer dribbles and fish blood. The light green ones look good (I've got a pair) but they get dirty fast and don't stand up to the trunks-as-a-napkin for all meals test. On my two week trip I brought just two pairs of these (and one pair of "go home" shorts but we'll deal with that later)... and wore them the whole time- they're that good.
3. Short sleeve button up shirts: In the tropics, tee-shirts turn into sweat soaked, clingy layers of cotton insulation. If you want to stay cool you need to take advantage of evaporative cooling- and for that function, shirtsleeves are the way to go. Standard wear for me is my white Guayabera- this one's a total crack up. Think more Ernie McCracken (Bill Murray's excellent King Pin character) than Don Johnson; it's got embroidered roses, white on white, running down the front of the thing. Cheesy? Completely. But totally comfortable and there's no better way to fade into the back ground than to sport one while chugging a Ballena at the taco stand.
Hot tip: Throw in a long sleeve version to keep the sun off your arms and the mozzies off your back.
Check back for more (I'm hoping to update from the road).