Anyone have preferences for mapping and route planning software? I’d prefer linux or osx based, but I know better than to expect anything useful.

I’d love to be able to add a bunch of intended waypoints and have something calculate the best route to get though them. Bonus points if it has options for suggesting particular roads or types of roads. If there is a web based site that allows that, even better.

Microsoft Streets & Maps? Delorme? Rand MacNally Atlas? Others?