The first step in taking a roadtrip, is planning a roadtrip. And the first step of planning is, of course, choosing your destination. But remember, like life, its not about the destination, its about the journey along the way. Choose a route where you drive through many exciting things and places. You want to look forward to where you end up the next day, not where you'll ultimately end up. Make sure to use a map to plan out your route. And if you want to be even more adventurous, then take a different route on the way back (which should be mapped out too). Roadtripping is about freedom. You don't want to plan yourself a strict schedule. You do, however, want to map out a route. Take your freedom, but be safe and cautious. Don't just take a road and follow it wherever it may lead you. Some people may like that kind of freedom, but I'd rather by safe than sorry. At least try to just map out the cities. You can always skip one, or add a new one, at your hearts desire.
As for the attractions, make a list of what you would like to see, and how long it'll take. Make a note of what is most important to you. That way you won't be too disappointed if you can't find in everything. Make sure to write the prices of the attractions. I would write down the open hours as well. You don't want to show up somewhere and find it already closed. We're trying to save money here, so always keep an eye open for coupons.
Before your trip, always check your vehicle. always. always. Make sure your vehicle is in good shape and repair, give it an oil change and possibly a tune up. Check your tires. Bring with you an emergency car kit and have an emergency backup plan.
Now create a budget. This is important for roadtrips. Plan out how much you will need for gas, accommodations, food, and sightseeing/attractions. I would recommend saving $200 for emergency funds. Make sure to stick to your budget. You don't want to splurge on a luxery hotel when you only have enough money for a hostel; you will short yourself out at some point.
As for what to bring with you, pack light, but don't forget any essentials. Pack clothings is that is right for the season. Choose layers than can adapt. The weather may change on you. When I went to Florida for the first time, it went from bright and sunny to pouring rain in less than two minutes. It definitely was a surprise! A toiletry kit will be useful and easy to carry from place to place.
Good planning will reduce stress. So have fun, but take your time planning.
Here are some great resources to check out:
Also check out this website: http://www.roadsideamerica.com/