This is how I typically plan my trip:
1. http://skyvector.com/ to check initial distance. This will tell me how many flying days should be planned.
2. http://airnav.com/plan/fuel/ Break trip down into 200 mile legs. Find 6 routes (or so). Provides rough idea of intermediate stops.
3. Check airport comments and nearby alternates. Eliminate poor reviews. Elevate those with interesting comments. I'll also check comments on AOPA. I prefer places I've never been...adds to the adventure for me.
4. I plan 600 miles a day for travel (2 fuel stops before an overnight) Consider "on airport" dinners/restaurants. Check on accommodations, for me AND Sally. (I like to actually talk to someone at the FBO if I plan to spend the night.)
a. 600 miles ~ 6 hours. That's enough time for me to be flying a small airplane each day. Add in preflight, fueling and securing the airplane it easily turns into 8 or 9 hours. If the weather is good and my energy level is good I can skip a stop. But I'm usually ready for a break after a 2 hour leg. Reference here
b. What do I talk to the FBO about? Hangar or tie down. Services available. Transportation options (crew car?). Any preferred hotel (discounts?) etc. Do they sound like good people?
5. Review for hazards (SUA, terrain, TFR, etc)
6. Break the trip into day trips.
7. Enter plan into Pilot (or Foreflight) Check NOTAMS. Adjust and finalize.
After a GO decision I enter the plan into my 696 and put my tablet in the bag. The tablet goes into the FBO with me if I need to change the plan.