Begin by creating a word processing document so you can type your planned trip out. This is not mandatory, but highly recommended. You don't want to miss the tour of the Eiffel Tower because you couldn't read your own handwriting!
Use a structure that appeals to you visually and organizationally. Create a header at the top of your itinerary with the destination and the full dates of travel. Every time you look at the itinerary before you leave, you will see those dates and they will imprint in to your brain. You will be much more comfortable on a trip if you feel like you know the plan like the back of your hand.
Divide the itinerary by day or time of day. It is easier to divide your itinerary by day, but if you have a ton of activities planned, you will benefit from dividing your trip by sections of the day. For example, "Thursday, May 31, 2007 - Morning".
Use start times (or approximate times) to organize each day. If you are traveling independently or with family, these start times do not have to be as strict as they might be on a business trip or on a group tour. Having a rundown of the day's events will help you tremendously. For example, "9 a.m. - Breakfast. 10am - St. Paul's Cathedral. 1p.m. - Lunch." Some people hate having an hour by hour guide controlling their travel. If you are that person, at least write down what activities and sights you are interested in so you can take full advantage of your trip.
Space out your events on the page for easy reading. If you are taking the time to plan a trip, the last thing you want is a hard-to-read guide. Create a structure so that your eyes will go to the most logical places (dates, times, vital info). A good way to do this is to left align all of your start times for activities and use tabs to space out the text.
Include as much information as possible. Phone numbers, addresses, email addresses, bus or train routes, flight confirmations--anything you can think of! Even if it's something that seems trivial, having all the info on your itinerary will be a lifesaver. Think about everything you do in a typical day...something as simple as getting dressed. If you live in Florida and are planning a trip to Alaska, include the weather forecast in your itinerary!