When it's just my family, we leave around 6am from San Jose. For a period of five years or so, we had a small TV and the Dreamcast set up so my little brothers didn't fight/annoy my parents with the incessant question of "Are we there yet?" We always stop three times on the 365 mile journey: first at a McDonald's to get breakfast for my dad the driver and so my mom can go to the bathroom, second at Harris Ranch to fill up the minivan and so my mom can go to the bathroom, third at Valencia for lunch and so my mom can go to the bathroom. As we enter Orange County us three kids try to see who can see the Matterhorn first/spot the Harbor Blvd/Disneyland Drive exit signs first.
When it's me and some friends, I'm usually leaving from Downtown Los Angeles, so it's a bit different. We leave around 8am (as it's a day trip on the weekend) and whoever has shotgun controls the music. We play two games: who can see the Matterhorn first, and when are we in Orange County (it becomes super easy to tell once you've driven in LA County a lot). As we take the exit for Disneyland Drive, I switch my ipod to my playlist of Disneyland ride songs. I always play Splash Mountain as I get to the booth for the Mickey and Friends lot.