Anyone know of any trip/routing programs for Mac?

[CaliforniaMini]

I'm going to be starting a new gig soon and need something to help with routing. I'm envisioning something where I can input, say 50 addresses, all within close proximity. The software then plans out the best route between them then sends that to the iPhone so I can use it as GPS in the car. But I don't know if something like this even exists, especially for Mac. I see some options that were made for hiking or running, and others for Windows that do some of this. Anyone know if this exists anywhere?

Thanks!!!
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Mini 2.0GHz (Early 2009), 4GB RAM, 320GB 72k RPM HD

[Rightondamark]

No first hand experience, but I've read about RouteBuddy being a good trip planner. It also ties in with the iPad and iPhone.

http://www.routebuddy.com/