Start with a self-assessment. How do you feel about road trips? Do you just want to get there fast or do you want to stop in at roadside attractions? If you just want to get the drive over with, you probably want to use an online map tool such as MapQuest.com or Maps.Yahoo.com to find the quickest interstate routes. These maps also often have the latest road conditions or construction information.
Visit the official websites of the states through which you will be traveling for interesting diversions. If some famous diner and its monster-sized pie or the world's largest petting zoo appeal to you, decide how much time you are willing to add to your trip. Online mapping tools often allow you to click on the line drawn between your destinations and drag it to include a different highway. The tools will also tell you how much time you are adding to your trip.
Decide on the types of hotels and restaurants you prefer. If you are more comfortable with large hotel chains and restaurants and their more predictable quality standards, you should stick to interstates where those establishments are located. If, however, you prefer local restaurants and bed and breakfasts, you should include some small towns along the way. Check the quality of accommodations by reading reviews on websites such as TripAdvisor.com.
Decide on the number of hours you do not mind driving, and then factor in the amount of time it may take to visit an off-the-path museum, for example. Only spend an hour or two at the museum in order to keep your schedule. Doing so will also help you stick to your budget.
Make sure your automobile can manage the route you have chosen. If you do not have four-wheel drive, you might want to avoid mountainous back roads, unless it is summer, as snow can linger around for nine months of the year in higher elevations. Think of other conditions you might encounter, such as muddy or sandy roads.