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I’m not a 100,000 mile/year traveler. But I do travel enough to get the basic elite status on most airlines (somewhere between 25,000 and 49,999 miles/year.) I refresh the tech I bring along relatively frequently, so here’s a snapshot of what I’ve been lugging around.

Apple MacBook Air ($1699)
No, I didn’t spring for the SSD. I just picked up the basic 1.6GHz model, spinning platters and all. The MBA is quite light and carrying it as the only thing in my bag would be awesome. However, since there’s no replaceable battery, forget about using it for anything longer than a US transcontinental flight. I also bring along the charger.

Western Digital Passport 250GB
I use the Passport to load up all of the entertainment that won’t fit on my MBA. Usually will try to keep a few DVDs from home that I’ve ripped stored on here for some in-flight entertainment. It’s great because it’s small, sleek, and is USB bus-powered (meaning I don’t have to carry-on a power adaptor for the drive.) Just make sure that your computer can send power through the USB ports (most newish laptops can). 

Nintendo DS Lite ($149)
As much as I love staring ahead at the tray table, sometimes I need something a little more stimulating. And when I’m not noshing on the banana/Twix combination I usually pick out for myself on the shorter NWA flights, I’ve got my trusty DS Lite. I usually leave the charger at home because the battery life is solid. I’ve beat a majority of the Phoenix Wright series while on the plane. Currently working on Professor Layton. It’s always nice to have the NYT crosswords handy, too. If you wanted to be bold, you could grab an R4DS or CycloDS Evolution and load up as many games as your heart (or micro SD card) desired, so long as you don’t mind wandering into legally ambiguous territory.

iPhone (3G)
So I’ve been carrying around the original iPhone until recently when I switched to the black 16GB 3G. It’s a must. I have most of my music and podcasts stored on here. Maybe some videos just in case I use all the juice of my MacBook Air.

Jawbone 2 Bluetooth headset
Friends don’t have to hear annoying gate announcements when I call them during a layover. The new Jawbone is sleeker than the original fatty version.

Bose QuietComfort 2 Headphones
Say what you will about the dubious Bose price/performance combination, but these are great to have on the plane. The only problem is that they add a bit of bulk to my messenger bag.

Future:
I’m looking at possibly picking up a netbook of some type now that there are a gajillion of them running around with that Intel Atom 1.6GHz proc. I’ll have to weigh (ho ho!) the differences between the netbook and the MacBook Air and see if it’s worth sacrificing some processing power and screen real estate for miniaturization.