I don't really consider myself to be that adventurous. Compared to some of the people I've met on the road - round the worlders shoestringing it (you know you're hardcore if 3 or 4 bucks a night for a room in India is too much and you sleep in a dorm for a buck) or the woman I met in Iceland who went on a road trip with friends in a small car from London to Mongolia - my exploits feel pretty tame. Those people are adventurous. Me? I just wander about sometimes.
I have, however, wandered about a fair bit, both in and out of Canada. In that time, I've developed an unwritten list of tools and tips that make the trip easier, things I make sure to take along. It wasn't until I started thinking about it that I realized how long a list it actually is.
1. The luggage - While my backpack collects more and more dust in my closet, I have not switched to suitcases. Instead, I usually pack a black duffel bag from Mountain Equipment Co-op. I have two sizes - one for weekend trips and one for anything longer. A lot of times I will take the larger one with me on short trips because it gives me enough room so I can pack my camera bag in it. I like duffel bags. I can sling them over my shoulder and carry them for fairly long distances without too much strain. Unlike backpacks, I can pack things a little better so I'm not always walking around with wrinkled clothes. Unlike suitcases, they can take lots of abuse. You can toss them under buses, drag them for short distances and generally give them a beating without worry. If your stuck in the middle of nowhere waiting for a ride, I'd much rather sit on or lean back against a duffel than a suitcase.
As for suitcases with wheels? I think they are great for the elderly or the infirm. Other than that, if you feel the need for wheels, you're likely carrying too much stuff. Don't worry, I know I'm out in the lunatic fringe on this one. Any trip to an airport or train station tells me it's a lost cause. In spite of this, I can't bring myself to buy a bag that rolls.
2. Camera strap - Want to know a secret tip about taking good travel photos? It's quite easy, though not without some sacrifice. First, take your camera out of your backpack or suitcase. Second, hang the camera around your neck. You'll start taking better photos almost instantly. Why? Simple. You no longer have an excuse to pass on this shot or that shot because you couldn't be bothered digging out your camera. The more shots you take, the better you get at composing them, finding the image that resonates rather than the image that was easy.
The sacrifice? You look like a tourist. The secret? You probably look like a tourist anyways, so you're not giving up much.
3. Memory, lots of it - It's the digital age. For the cost of a couple of plastic squares, you can take far more pictures than you would have with film. Even better, you don't have to change the cards that often. I was thinking of this on a cold, wet day on a crowded amphibious boat/bus thingee in Iceland. If I'd been shooting 35mm, I would've missed most of the good shots.
Just make sure to edit for content later. Just because you can take 53 shots of the same iceberg, it doesn't mean your friends or family want to see all 53 shots.
4. Travel alarm clock - Yes, there are places out there that don't do wake up calls or room service. A small alarm clock solves one of those problems.
5. A stuff sack - The same type that backpackers and outdoorsy folks use for their long treks in the wilderness. I take an empty one along for dirty laundry, mostly socks and underwear. While I will reuse shirts and pants with reckless abandon, I don't often do the same with the aforementioned socks and underwear. A stuff sack is a great place to put them.
6. Ipod, folding headphones and travel speaker - Not only will having your own pair of comfortable folding headphones (my ears were not made for earbuds) save you a few bucks on the plane when you want to watch a movie, travel speakers and an ipod make hotel rooms much more enjoyable. There's only so much french or spanish or icelandic tv I can watch before it all starts sounding greek to me.
7. Pocketknife - A million uses, most related to impromptu picnics (ones with corkscrew and/or bottle opener are best).
8. The US dollar - It really is the universal language. Take a small stash with you and keep it for emergencies. I remember getting to the Nepali border at night and all the Brits scrambling because the border officials only wanted greenbacks, not British Pounds.
9. Converters and adapters for electrical devices - It pays to do your research. Ipods and most laptops will work on 120v or 240v, so all you need is the proper plug adapter. Other items (Nintendo DS, for example) only operate on 120v, so you need a plug adapter and a power converter. Personally, I'm fine with carrying a plug adapter but not much more. Anything requiring a converter gets left behind.
10. A yahoo/hotmail/whatever web based email account - You can find internet almost anywhere. On my trip to India and Nepal that was the main way I communicated with friends and family. Same with Iceland. Set up an account before you leave. Perhaps make it a different one from your everyday account in case anything happens to it (I've never had any issues, but it's worth it to be safe).
11. Guidebooks - I generally use Rough Guide or Lonely Planet. Buy the book well before you leave and browse through it. Find the things you would like to see. Get a basic understanding of the cultural differences. It can be mildly disconcerting having an Indian tell you yes while shaking his head no (in India, the head shake - sort of reminds me of a figure 8 - is a sign of agreement). Take the book with you and use it but don't be afraid to try something that isn't in the book - guidebook writers can't get everywhere and, besides, things change. The books are worth it for the maps alone.
12. A money belt - Nothing beats simple awareness and common sense for keeping thieves at bay, but a moneybelt does help. After a while you get used to wearing it.
13. A decent toiletries kit / a first aid kit (for more adventurous destinations) - Be strict but don't skimp too much. Buy a pack of plastic containers from a drug store and use them for soaps and shampoos. Pack some tylenol and immodium (Moctezuma's revenge can strike you anywhere, not just Mexico and it can make travelling suck). Make sure you have enough of what ever medications you take so you can handle being delayed for a couple of days. If you are taking prescription meds, take a list of them along and keep a copy in your daypack and in your toiletries kit in case something happens.
14. Travel insurance - Buy it for any trip outside of Canada, even / especially to the States. It's fairly cheap, but gives you that peace of mind you need. Leave a copy of the info. with someone at home and take copies with you (perhaps on the same sheet you use for listing meds).
15. A good book - You knew this one was coming. Leave the portable dvd players and ds's at home. Take a book and enjoy it. You're on vacation.