Set your budget. This is particularly important on a road trip as your spending can easily run out of control if you're not careful. You'll be paying out for rooms, meals, gas, admission to tourist sites and plenty more every day, so decide how much you want to spend--and stick to it.
Decide if you want to take your trip at home or away. There are lots of great options across the United States, while if you decide to go abroad you can be sure of having loads of memorable experiences.
Avoid being too ambitious. If you go to Europe you'll find you can explore much of what a smaller country such as Portugal or Ireland has to offer in a two-week break, while in larger countries such as France or Spain you'll need to confine yourself to a particular route or region.
Choose what kind of trip you want. You could stick to the coast, stopping off at seaside resorts and secluded beaches along the way. Or you might prefer to go across country and lose yourself amid beautiful scenery. Or you could pick a classic city-to-city route such as Los Angeles to San Francisco. The possibilities are endless.
Book only the things you have to. The joy of a road trip is that you can be flexible so you won't want to plan every detail of your vacation. If you're flying then obviously you'll need to book your air tickets, car rental and perhaps a hotel for the first night or two in advance. Otherwise keep your options open so you can really enjoy the freedom of the open road.