3RD Place: InRoute
InRoute has a free and a premium version, and the premium is good enough that your dad might splurge for it. Essentially, it’s your standard app, only with the ability to add stops — up to 5 stops for the free version, and 25 for the premium version. The premium version also lets you map out how much time you want to spend at each stop. It’s basically an app designed to encourage your dad to take the family on a Road Trip.