Polarsteps easily tracks stops on roadtrips and flights - the trip tracker is awesome. Also love the profile page, especially the overall map view that has the red dots to show all trip stops - the only thing I'd want to see improved would be being able to see that map up close.

Make sure your route is broken down into doable driving segments both to and from your final destination. Your plan should also include a list of attractions you want to see along the way. Tip: Ahead of your road trip, research attractions' hours and visitor guidelines. Reservations may be required.