When it comes to you and your stuff, there is no telling how or when you might be separated, whether briefly or permanently, in your trek from your car seat to your airplane seat and back again.
How safe are your belongings when you fly? In just the past few years, TSA employees have been caught running robbery rings and enabling drug trade. If security agents are robbing travelers, imagine what is going on among baggage handlers, gate agents or anyone alone with your stuff for the very brief moment it takes to steal something. Even fellow travelers have been caught nicking stuff from overhead bins during flight. You don't have to be paranoid and suspicious every moment of your trip; start out by trusting everyone, but don't make it easy for anyone.
Thousands of airline and airport employees do their jobs every day without even thinking of pilfering your bags. I have flown frequently for the past 30 years, and have been ripped off only once -- clearly I have encountered a true heap of honest, hard-working people. But it's not those normal folks you need to guard against; it's the one person (or group) who has figured out how vulnerable we are while traveling.
Perhaps the most important thing to know to protect your belongings from that one person along the way is this: the best thieves know not to steal stuff that will be missed any time soon. They want you to figure it out when you get to your hotel room a few time zones away. I've come up with a few simple rules that, while they won't protect everything you take with you, will protect the things that matter most.
All in One Place
Before you leave the house, put the important stuff in one place, and never lose track of it. A friend of mine has taken to putting her most critical and valuable items (identification, wallet, cash, jewelry) in a clear plastic bag that is obvious to everyone. "I 'hide it in plain sight,'" she says. "Then everyone knows what is in there, they have no incentive to open it to find out what is inside and I can see immediately when I get to the other side of the security machines if anything is missing."
You may not want to go the full Ziploc route, but a workable alternative is to reserve an obvious pocket of your carry-on bag to hold all the stuff you need in the airport and on the plane but can't take through a security machine. The benefit of having a single, dedicated location for valuables becomes obvious when you don't have to rifle your bags to figure out if your wallet is missing, or your boarding pass, or your driver's license, or your medication, etc. -- that 30 seconds before you finally find something in the bottom of a bag can take minutes off your life, oof. If you know exactly where everything should be, you won't fail to miss it the moment it disappears.
Say It Loud
I have also found it useful to state out loud what I am handing over to a security or gate person. When you say, "This has my wallet, my ID and my watch," and they hear you say it and see you put it down, they may be less likely to try to take something.
Two (or Three) Things to Have on Your Person on the Plane
There are really only two things you need to have on your person on the plane: your ID and a credit card (a third, which does not apply to everyone, is any essential prescription medications -- more on that below). If someone steals every single thing you brought with you, these are really the only things you cannot replace quickly and easily, and that you will absolutely need to get you out of pretty much any jam upon landing.
Almost everything else you can replace -- there are grocery and clothing stores everywhere -- but without both your ID and credit card, you can't rent a car, check into the airport hotel, buy food or, critically, get on a plane to take you back home.
Some folks would add their cell phone to this list, and they would have a point; if you are in a jam, having all your numbers and an easy way to call them (try to find a phone booth that works these days) could really make a difference.
Having the credit card easily available on the plane has an added benefit beyond the safety factor: it's usually the only way to buy a snack, a drink, headphones or an in-flight movie. Don't be the person dumping the contents of the overhead bin into the aisle just to buy a turkey sandwich; keep your card in your pocket.
Finally, the third thing to keep very close is any prescription medications; these can be difficult to replace quickly, and being without them could create potentially dire problems for folks with serious medical conditions.
Bury Your Wallet and Cash in Your Carry-On
Once you board the plane, you will have no need for your wallet and cash, as few airlines still accept cash payment for things like food, drinks or (unbelievably) pillows and blankets. My recommendation is to bury these so deeply in your carry-on bag that the only way someone would ever find them would be to take your entire bag and overturn it on the floor back at their own home.
Bag Inside a Bag
Anyone who has traveled extensively since airlines began charging for the first checked bag knows that the gate area of a full flight today looks like the baggage claim area of a full flight several months ago. Everyone has at least one huge bag that would barely fit in a bathtub, let alone into the little metal cages indicating proper carry-on size.
When the overhead bins fill up almost inevitably about halfway through the boarding process, gate agents are forced to check the bags of anyone unlucky enough not to have boarded already, almost irrespective of the size and contents of the bags. (It's gotten almost to be a joke; on a cross-country flight this long and cold winter, the gate agent announced, "We know it is very cold, but do not put your coats in the overhead bins, or we will check your bags.")
You never know if they're going to start taking your stuff from you at the end of the gangway, so my recommendation is to pack a small bag inside your larger bag in case you are forced to check your carry-on. This way you can take your most valuable (and most easily stolen) items, and put them in a small bag you can keep at your feet if necessary.
Anything You Really Care About, Wear It
You've heard the saying "You'll get it when you pry it from my dead hands" -- we all hope and pray it doesn't come to that, but for your most valuable things, this should be a phrase to, well, live by. If you don't want to lose it, wear it.
For more tips on keeping your valuables safe, see Money Safety.
What to Let Go
Unless you are going to a truly remote location, you can pretty much buy socks, a toothbrush, a pair of reading glasses, a raincoat, a book or breakfast anywhere. My feeling is that if you can buy it at your destination relatively cheaply, don't go out of your way to protect it -- especially at the risk of distracting yourself from protecting the things you really need. If it's cheap and ubiquitous, don't sweat it during your travels.
Beyond the Airport: At the Hotel and in the Car
The airport is not the only place folks have opportunity to rifle through your stuff when you are not looking. Every time you leave your hotel room, you should remember that a large number of people have keys to the room. Read our Hotel Safety Tips to learn how to protect yourself.
Of course, travelers also rely heavily on the meager security measures of their rental cars. An alarm is great, but it's a lot more effective if you don't have any valuable stuff in the car. And often enough you are forced to hand over your keys to underpaid strangers at restaurants, city parking lots, hotels with valet-only parking and more. Most of these folks are honest, but eventually your luck will run out unless you take some simple precautions. Check out Nine Ways to Keep Your Car Safe on the Road.