Here are things that it is difficult to imagine not packing:

Toiletries (Toothpaste, toothbrush, soap, shampoo, razor...)
Hair care equipment (brushes, comb, blow dryer) Contact lens equipment and spare glasses (You might also wish to consider disposable contact lenses)
Makeup
Condoms

Towels and clean sheets will be provided.
If you will be looking at ceilings (like on a castle or church crawl), bring a small mirror so that you won't strain your neck.

Clothes
(Try to take different colors of shirts/blouses; mixing and matching might fool people into thinking you brought more clothes than you did).

If you are going on an extended trip, pick one color and stick with it. If you are part of Generation X, rejoice, as black travels very well. You can get horse slobber all over your black jeans, and as long as nobody stands too close, you'll look fine.

Plan on inclement weather. It will happen, and everybody there will say, "Oh, it almost never rains/snows/hails/blows/floods like this! This is very unusual weather." In particular, be prepared for it being colder than you expect. I also recommend bringing a pair of flip-flops (also called thongs or shower slippers). If your shoes get wet, this gives you something that you can wear while they dry.

Miscellaneous

Day pack/Duffel bag
(If you are doing any sort of sightseeing, take some sort of small backpack or fanny pack. You will want to carry maps and perhaps phrase books, guidebooks, water bottles, sunglasses, and so on).

Neck wallet or money belt
This is especially important on the hostel/train circuit. Keep most of your money hidden away underneath your clothes. If you are as paranoid as I am, you might even want to go to a two or three-level system: keep passport, airline tickets, and the bulk of your money in a money belt, about US $50-100 in a neck wallet, and about US $5-10 in your jeans pockets.

Earplugs, water bottle (with water!), chewing gum, food
These can make your plane trip much more enjoyable. Aside from being noisy and prone to pressure changes, airplane cabins are very dry, and you will tend to dehydrate if left in one long enough. The gum helps with depressurization, and airline food is, well, about as good as airline food.

Passport
(Even if you are inside the country, it is a good idea to take your passport with you).

Watch with alarm
(A cheap digital watch with an alarm is small, light, and very useful).

Electrical transformers/plug adapters
(Most places in the world have different plugs and different power supplies. If you want to use your computer/modem/electric razor/alarm clock abroad, you will need to get equipment to translate from "your power" to "their power").

It is a very good idea to avoid controlled substances. You probably do not want an extended vacation in another country's jail system, even if room and board is free.

If you are traveling internationally, be very hesitant to take anything for anyone else, especially if you do not know them well. At best, the airlines will ask you lots of questions about what you are taking. At worst, the airplane will explode and you will die. (The Lockerbie crash, if I recall correctly, was caused by an explosive device carried on by a passenger for her fiancée. Nice guy.)

How To Put Your Stuff In Your Luggage
Whatever you pack your gear in, be sure to clearly label your luggage on the outside with your name, address, and phone number. (You might want to use a business address or PO Box instead of your home address.) Also put a piece of paper inside with the same information, in case the tag gets stripped off.

If you are traveling internationally, you should pack your own gear, then either lock it or keep it close to you at all times. If someone else packs your gear or you are separated from it, the best that could happen is that the airline will grill you about your luggage and possibly go through it. The worst that can happen is your airplane exploding from a bomb you inadvertently brought on.

Organizing The Space
You will undoubtedly want to organize the space in your luggage so that items are easily accessibly once you get to your destination. Plastic bags are Your Friends when it comes to this. You can pack your undies in one bag, your socks in another, your toiletries in another, and so on. (Don't forget to pack an extra bag for your dirty laundry!)

Avoiding Breakage
If you are traveling with anything breakable, surround it with soft and squishy items. Put your CD player inside a plastic bag, then put it inside a plastic bag filled with your socks. Put your Listerine bottle inside your one of your boots. You might also want to put your breakable item inside a cardboard box stuffed with foam or packing "peanuts", then putting that box inside your suitcase. The best way to avoid breakage is to take the item as carry-on, if possible.

Maximizing Space Utilization
If you are having trouble fitting everything in, look for ways to use nooks and crannies. Fill the area around books with socks. Put your modem cables inside your shoes. Also, you can cheat a little bit on the carry-on. Wear your jacket on the plane instead of putting it in your suitcase. (This is not a bad idea anyway, since airplanes are frequently cold.) Put your toothpaste, earrings, modem, or even a few pairs of underwear in your coat pockets.

Selecting Luggage
Having appropriate luggage can make a world of difference. It may mean the difference between carry-on and stowed (which may mean the difference between lost and not lost!), health or a hurting back, and damaged vs. undamaged belongings.

Note: This article assumes that you are packing for a plane flight; traveling by train, bus, or car may be slightly different.

Garment Bags
Garment bags can be exceptionally nice for short business trips. Most airplanes have little compartments with a bar that you can hang them on. Be advised, however, that those compartments fill up pretty quickly, and you may have to jam it into an overhead bin, wrinkling your suits and dresses.

However, garment bags are not particularly easy to carry if very full or for a great distance. (Note: I have never been a broad-shouldered, narrow-hipped, tall, strong man, so perhaps there is a class of people for whom this assertion is not true.)

Wheeled Luggage
If must take heavy items (like, for example, six computer manuals and a replacement power supply), seriously consider some sort of wheeled contraption. One can purchase carts that can fold up and go inside the suitcase or suitcases that have wheels and a handle built in.

Suitcases with stiff, center-mounted racks are much more manageable than suitcases with "leashes". The leashed suitcases have a tendency to wobble, tip, get stuck, fall over, etc. The leash is always too short for your height, so you end up walking hunched over anyway. Leashed luggage is exceptionally ill-suited for those lovely, picturesque cobbled streets that your charming little pension with no elevator is on.

A good, hard-sided suitcase with a rack can be a bit pricey - up to $300. However, consider that this is much, much, MUCH cheaper than back surgery.

Cheap Luggage
On the opposite end of the spectrum, you should remember that it is not mandatory to purchase a special valise for carry-on items. A few sturdy garbage bags can work just fine.

You can also put things in boxes. Be sure to wrap them extremely securely with glass-reinforced tape, and recognize that they will get very rough handling. Furthermore, the airlines will not take responsibility for damaging anything in a cardboard box. You take your chances.

Duffel Bags
For long-term, low-end travels (e.g. the Grand Eurail Tour of Europe), my personal luggage of choice is an old, beat up, blue nylon duffel bag. It is large enough to take a week's worth of clothes (if I am not too fussy) and small enough that I can't fill it fuller than I can easily carry. It fits in the overhead compartment and it weighs practically nothing.

Furthermore, it does not scream "Wealthy Tourist!!"; I could just be returning from figure-skating practice or something like that.

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