- Any Bill Bryson travel book (In a Sunburned Country being an excellent option) - Bill Bryson's writing taught me two key travel lessons: (1) when things go wrong (and eventually they will go very, very, wrong) you have a choice - get upset or laugh. Bryson taught me to do the latter. (2) Bryson has a knack for seeing and appreciating the small things about travel. By learning to do this, every place, no matter how mundane, becomes a joy to travel to. (Cost: Free - rent it at the library.)
- A Blogger account - It's amazing how quickly a vivid day of travel fades from memory. After a few months, a week long vacation packed with adventures seems like a hazy collection of just a few memories. The best fix I've found for this to to keep an online travel journal. A few photos and notes from a days adventure goes along way towards making your vacation memories permanent. Do this for yourself. Do it for your children and your children's children. Could you imagine reading your Grandmother's travel journal from when she was 18? Don't do it to become popular on the Internet. Oh, and be careful, journaling can get addictive. I often need to remind myself to not try to record every experience, if I do, I just go nuts. (Cost: Free)
- A Fordors guide to the area I'm visiting - I suppose any travel guide will do, though, through the years, I've always depended on Fodors. Travel can be a surprisingly difficult activity - being in an unknown city, with an unknown language, can be both exciting and overwhelming. A Fodors guide becomes my security blanket. I helps me find a place to eat when I seem to be in a part of the city that has no restaurants, things to do when everything seems closed, and side trips when we've exhausted all the local attractions. Heck, it'll tell you when to tip and how much. My general rule is to scan the guide before I leave, really delve into it on the airplane ride over, and then use it as needed when I'm traveling. I don't let the guide dictate what I do and don't do. (Cost: Varies - usually around $15.00)
- A sleep mask, head phones and chill music - This is my sleep-on-the-plane system, and I've found it to be amazingly effective. The sleep mask I use was a free one I've picked up along the way. The headphones can be nothing special, though I like my Etymotic Research ones and chill music can come from a variety of sources: a cell phone app, mp3 player or even the XM radio offered by certain airlines. I just know that combining these three items means that long flights with noisy children become totally bareable. (Cost: Varies - less than $30.00 if you're clever)
- A Google Reader Account - By using Google Reader you can easily read other traveler's blogs and generally get tips on how to travel better. As they say, the more you know, the less you need. (Cost: Free)
Interestingly, while writing up this blog post I found addressed a similar question some time back. Without realizing it, I've basically written up the same answer - though with some slight variation. I guess I still feel pretty strongly about these items.