1. Food. I always pack at least one protein bar, and maybe some raw almonds. If you wait until getting to the airport, and through security, to purchase your munchies, be prepared to fork over your wallet for a usually-not-too-good selection.
2. Water. Buy the biggest bottle you can find once you get past the security checkpoint. Buy two. You can never have too much water.
3. My iPhone. While I may still be rockin' the iPhone 4S, it still can't be beat for its camera, guidebooks, maps, travel apps, games, communication, and music.
4. Travel documents in a pouch (or two). Although I tend to also keep these items digitally, it's sometimes good to print out your various reservations and tickets to bring along. I use a large Tom Bihn clear/Dyneema organizer pouch. I'll also use a Tom Bihn RFID Blocking Passport Pouch for my passport and credit cards.
5. Toiletries. Even if I'm only going for a long weekend in Florida, I still bring, at a minimum, any prescriptions, a toothbrush, small toothpaste, small deodorant, dental floss, lip balm, gum, moisturizer, a few individual wipes. In case of a delay, I know that I can at least keep fresh. All of this fits nicely in my Tom Bihn 3D Clear Organizer Cube.
6. Spare undies. I don't think I need to explain. I swear by ExOfficio's.
7. Noise-canceling headphones. Expensive? Yes. But if you travel frequently, you'll appreciate the way they block out engine noise, as well as your chatty seat mate.
8. Kindle Paperwhite. This wasn't on my last list, because it didn't exist yet. Never again do I agonize over what reading materials to choose. Now I can bring everything!
9. iPad. I purchased my iPad 3 with Retina Display over a year ago, and it has practically replaced my MacBook. I realize that the iPhone can do almost everything the iPad and Kindle do, but I like the screen real estate.
10. Evernote Moleskine. While I've had an Evernote account since almost Day 1, I haven't used it to its fullest until now. I just recently purchased this notebook which allows me to capture all sorts of things into Evernote - travel writings, plans, recipes, contact info - you name it, I can put pen to paper, then capture it all electronically into my Evernote account. The bonus is that the notebook comes with 3 months of Evernote Premium.
All of the above now goes into my Tom Bihn Synapse 19. I cannot stress how much I absolutely LOVE this bag. I've been using it every day, even when not travelling, because it is so well thought out and sleek looking. It holds WAY more than it looks like it should. It's durable. Did I mention it looks great? If I don't want to use a backpack, I'll grab my Tom Bihn (are you noticing a theme here?) Co-Pilot for my carry-on. It makes a great day bag, and it fits beautifully under the seat, leaving plenty of room for your feet.
Other than these 10 essential items, and depending on my destination and time of year, I'll often also carry a rain jacket, extra shirt, and maybe a really thin fleece top.
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