I know this is technically a cruise forum, but I thought that having just taken a roadtrip (probably my first sans parents) I would write an article on how to plan one out, so here goes nothing.
Step 1: Picking a Destination
First figure out where you want to go. Make sure you have what you want to do in mind while you're picking out a place to go. Check out a variety of places, and also have a Plan A. and Plan B. Make sure you consider all the different amenities available in the particular place you are going and what may be en-route as well, because making a pitstop can also be beneficial to the driver (whether it be you or someone else).
I highly recommend traveling somewhere that you have someone you know that can show you the area and is at least somewhat familiar with the area to which you are traveling. Road trips are also an excellent opportunity to connect with old friends, or meet some new ones.
Also to consider is PRICE, especially if you're doing it as a solo trip, or if you are thinking about going somewhere pricey (e.g. New York, Miami, Orlando, Los Angeles, etc... you get the point). Make sure to establish a budget early.
City of Philadelphia
Step 2: Establish a Budget - Determine How Much You Want to Spend
Step two is to determine a budget. Set yourself a budget - I am going to spend X amount of dollars on this trip. And while you are on the trip STICK TO YOUR BUDGET. You don't want to come home to an empty or overdrawn bank account because that would suck. Make sure to account for hotel(s), gasoline, tolls, and food. Also consider setting aside money for parking, nightclubs, and other discretionary expenses. If you're looking for something cheap and easy, set a low budget, but keep in mind that the further you go from home and the bigger the city and more amenities, the pricier the cost of the trip is going to be.
A budget is extremely important
Step 3: Bring a Friend or Travel Solo?
A big decision to make in taking a road trip is whether to bring a friend or friends or to travel solo. Personally, I think having a friend or girlfriend or boyfriend or someone you're close to with you makes a HUGE difference. If you're good enough friends, you can split the cost of the trip (less pain on your wallet). Also, having a friend definitely makes the driving a lot easier, especially if it is a longer distance trip - you have someone to talk to, someone to entertain and be entertained by, and someone to take pictures of all those lovely sights you'll be seeing. Keep in mind that you have to be really comfortable with whomever you're traveling with...you'll be sharing a hotel room if you're sleeping over.
Step 4: Make Reservations
Make your reservations for your accommodations if you are sleeping over 1 or more nights. Book your hotel, make dinner plans if you are making it a romantic trip as well as road trip. Keep copies of anything and everything you reserve, whether on your phone or a laptop or a printed copy; you'll be using them in the future during your trip. I recommend using Kayak (
http://www.kayak.com) to search for reservations. Keep in mind that most hotels have varying age limits. Call ahead of time BEFORE you reserve a room.
Step 5: Plan the Traveling, Stops, and Timing
Plan out your pitstops, the route you'll be traveling (use a GPS unit - it helps so much especially when you feel lost in the middle of nowhere or when you want to find points of interest), and where you would be interested in stopping. This would be a good step to sit down and do with the person(s) you'll be traveling with.
Check out what there is to do along the route. I recommend using Google Maps (
http://maps.google.com) if you are looking for specific things around a city or town. I recommend beach hopping if you can; a lot of the time this can be a lot of fun, but don't forget to bring the sunscreen, towels, and a change of clothes or you'll be very uncomfortable along the way. Check out historical cities and landmarks if you can - these make awesome picture spots, even if its just to make fun of the "wacky looking Indian statue (no pun intended)".
Establish a timetable. Remember that you are trying to get somewhere. Don't dwell on one place along the way too long, because the best is yet to come. Get to your destination at a decent time - if you are staying at a hotel, generally after 3 p.m. (check in time). Keep in mind the total drive time too. You don't want to stretch it out too long or it won't be any fun.
Use a MAP!
Step 6: Pack Accordingly
If you are traveling with more people, then keep in mind the trunk space of the car you're traveling in (my small Scion Tc won't hold much baggage, but a Chevy Suburban will). Also, remember toiletries, sleeping clothes, and a change of clothes if you're staying over in the city. Bathing suits, and a change of clothes if you're going to the beach, and SNACKS for the ride. Water/drinks, and a cooler are also very good to have, particularly in the summertime.
Don't forget the iPods, chargers, CDs, and other forms of entertainment (DVDs/Players, etc...) I would also recommend a laptop in case you need to make reservations on the run, or if you need to look something up while on your trip. Don't forget the camera, batteries/charger, SD Cards/memory, and the cable to unload pictures if necessary.
Step 7: Enjoy Yourself
Enjoy yourself - relax. If things don't go as planned, who cares! You're on vacation. Meet up with friends, do whatever you'd like. It is, as they say, your party.
My Road Trip to Tampa with the Girlfriend. Thanks to Lauren (I_Live_4_Cruises) for coming out to hang with us. 
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Guide to Planning the Perfect Road Trip (Pics included)
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