Well Traveling by plane outside the USA is quite an experience. Its been a while for me, I am sure others possibly do it all the time. But here is a few things I found out by watching others and myself as I crossed into British Territories.
Carry-on, Take the smart phones! & Camera, As the tablets might take over a smart phone is all you need. ATT with an international small additional fee was a clear winner over Verizon. My dad had to get a different chip for his Verizon phone. Take your Snack bars and sandwiches with you on the plane. Do not take any water or liquids. They will be provided for free. There is some strange problem with taking lithium batteries. They do not mean the AA's they mean spare Phone batteries, possibly shorting out and catching fire, tape them up. Make sure you change your message and know your password before you leave - we had no access to our messages - we didn't know a code for voice mail
Backpack - fully loaded and checked as baggage. a small UL pack will make it as carry on, but will trip you up with all the checks. Knifes can be in baggage but not on carry on, so stow it. I watched a few people yanked form the line to explain privately what was in their stowed luggage. I also watched 10 percent of the line diverted to a guy who swabbed QTIPS in womans purses, and mens hands for the cocaine machine.
Coming back into the USA I dumped all metal including coin. I switched to a web belt to speed things up. And accidentally got into that new radar/xray machine that can see you naked... Oh well It was quick easy and got through the line again quickly. Having a stripped wallet of just necessaries and your passport in your pocket and a plastic pen for the forms really speeds things up! I kepted a few Caymen ones and American ones for tipping good baggage handers, and taxi folk. There are two checkpoints now, one for TSA, one for Customs, Bags are dumped and rechecked back onto the destination planes. The lines are long & slow for people that don't pay attention, at one moment the room at the TSA is empty to step into the men's room and come out a couple of minutes and you are 200 people back. ( No kidding )
Above all, before you decide to go hiking in another country, make sure you understand what the current exchange rate is. Understand what is going to be hard to get when you get there. Right now Cayman Islands have $6-7 dollar a gallon rate and a loaf a bread can be $5-6 a dinner a so so restaurant can average $35 - $55 a person. Why ? - in the last two years our buying power internationally has tanked.