In December I spent two weeks traveling around Costa Rica, from Guanacaste to the Osa Peninsula and places in between. Except for the Kelty Station daypack holding my laptop, camera, pens, etc., I did it all out of a 22-inch wheelie carry-0n.

I’m getting ready to get on a plane and head to the Outdoor Retailer Winter Market in Salt Lake City to check out all the new gear coming down the pike we may want to review over at Practical Travel Gear. So it seems like an appropriate time to run down what helps me pack in such a compact and light manner for a two-week trip.

Take a Lightweight Bag

First the bag. Normally I bring something without wheels, like a backpack, but this was a work trip where I knew I would be mostly in airports, taxis, and hotels. So I used the Eagle Creek ORV 22 wheelie suitcase pictured here. It’s not super-light at 7.5 pounds, but light enough. It holds 43 liters (2,600 cubic inches). You can cram more than this into a carry-on if you ditch the wheels, but keep in mind some airlines also restrict the weight. That includes Nature Air where I was in Costa Rica, but also many budget airlines in Europe and Asia. The heavier your bag, the more you’ll pay.

Go Easy on the Shoes

Speaking of weight, shoes are the big killer, so I usually only travel with two pairs of travel shoes, wearing the heaviest pair on the flights and bus rides. Sometimes I’ll break down and bring a third if I need water sandals or dress shoes for some reason, but at least one pair has to be really flat. If you must carry sneakers for a workout, these New Balance WT100 travel sneakers pack down to nothing and are wispy light: they’re all mesh at the top and have a thin footbed.

Leave the Jeans at Home

The weight of your clothing can add up surprisingly fast as well, especially if you’re packing blue jeans, normal corduroys, or khakis. I’m a huge fan of lightweight, quick-dry travel clothing from the likes of ExOfficio and Columbia Sportswear. I find life so much easier on the road with a wardrobe of this stuff in my bag: the clothing weighs very little, it stays relatively wrinkle-free, and it looks nice enough that you can look respectable at a restaurant or meeting. Sure, it’s not all that cheap, but I’ve got ExOfficio shirts I’ve been wearing for years that still look like new. And hung in the sun, they dry in 15 minutes. Heck, I even pack their travel underwear for the same reason.

Carry Only the Cosmetics You Need for That Period

Too many travelers play the “what if” and “just in case” games when packing their toiletries and end up bringing half the medicine cabinet. With reusable plastic bottles and sample sizes you can bring enough for two weeks and still stay under the TSA carry-on requirements. Plus you can buy whatever you really end up needing locally—usually for the same price or less. Sure, there are exceptions that are a bit tougher, like sunscreen, but not many.

Pack Double-duty Travel Gear

If an item you’re packing only does one thing, it had better do it really well—like a SteriPen or a solar gadget charger. Part of the way I pack lighter is to carry double-duty gear that can perform multiple functions. A belt that holds money, pants that can also be shorts, long-sleeve shirts with button-up sleeves, a coat that converts to a neck pillow, a keychain that’s a corkscrew or bottle cap opener, or a watch that’s also an altimeter and compass.

I love to rag on the Apple hype machine, but I have to admit the iPod Touch is the ultimate double-duty item. The electronic equivalent of a Swiss Army Knife. Carry one of those tiny packages and you’ve got all kinds of apps and e-mail access, yes, but you also have more mundane helpers travelers needed even before the Internet Age, things like a calculator, currency converter, language translator, alarm clock, music player, and (Skype) phone. Put SugarSync on there and you’ve got all your home files with you at all times as well.

Do you travel two weeks or more with a carry-on? Put your tips in the comments!