Road Trips are a great way to vacation. They let you have a flexible itinerary and cover as much or as little distance as you like.
Road trips can be a relatively inexpensive holiday if you are flexible about the types of hotels and motels you use and don't always go to fancy restaurants. I have had good luck using the hotel discount books from rest stops and visitor's centers to find reasonably priced places to stay. On my most recent one month road trip, my average lodging cost was less than $55 a night. I have had very good luck on getting acceptable place to stay without having reservations.
Modern technology has made road trips even more interesting, safe, and fun. Three of the most important technological breakthroughs for road trips are the Internet, cell phones, and GPS.
If you like offbeat attractions, such as Shoe Trees, Muffler Men, and strange museums and theme parks, then www.roadsideamerica.com is a very useful resource for planning your US or Canadian road trip. There is detailed information about sights which might interest you along your possible route and tools to plan your journey. Particularly useful is the ability to download custom Points of Interest (POIs) to certain GPS units.
I have done two long road trips in the United States. During the first one, I relied on hard copy maps; the second I used a Garmin Nuvi GPS unit. I am now a big believer in GPS, particularly if you will be spending time in or passing through large urban areas.
It is a good idea to phone attractions in advance if you are not sure of the open hours or days. I drove 18 miles out of my way to visit the 'OZ Museum' in Wamego, Kansas only to arrive 5 minutes after it closed.
I think that the best way to plan a road trip is to pick a general direction with 1 to 3 primary destinations, and then find additional minor stops along the way by doing research before you leave.
A few suggestions: 1) Bring a lot of snacks (I like dried fruit, Punjabi Mix, and M&Ms) and fast breakfast items (instant oatmeal, fruit, etc.), 2) Travel light, 3) Service and inspect your car in advance of your trip. There is extensive road trip planning information and a lot of information about my last road trip at my website: Eggyspace.blogspot.com.
I hope that you enjoy this type of vacation as much as I do.