I plan meticulously. As we don't have decades of riding behind us, I know pretty much what the physical limits are for the 3 of us who ride together, and how much driving to trailheads we can do in one day. We only ride the trails, but I've added mapmyride to my "tool kit" because it's so good at showing elevation changes. My goal is to put tread marks on every decent trail in my state, and at least one or two other states every year. Last year it was the GAP in Pennsylvania, not sure where it will be yet for this year. Fortunately for us there's a section of the Ohio to Erie trail right outside our door we use for fitness rides.