Unfortunately, I don’t have flexibility unless I’m doing a long weekend from or close to home and could conceivably take Monday off if something were to go awry. And close to home there are usually very limited legal camping options. Otherwise, I usually have a flight to catch. Thus, I plan each day and often have a backup plan for each day that may entail a shorter or longer day. But in the end, I ultimately have to be back at my departure city the day before my flight, at the latest.
Wasn’t always like that. I started touring when I volunteered to be downsized back in 1999. First trip was ACA’s unsupported Northern Tier. Daily mileages were usually kept on the easily manageable side. But then I rode home to Philadelphia solo with only a drop dead date that was far off for the distance, so I could make daily decisions about mileage. My next two trips the following year were like that. Although I had to catch a flight home from Spain after the second one, I had seven weeks to play with. Did a lot of original plan altering during that one. The third trip involved no flight home. I just had to arrive at Mesa Verde NP some time in the month of July. Took several unplanned rest days and some unplanned short days. IIRC, I finished a week later than I thought I would. A week after my arrival the park caught fire and I and the interns I was hanging with had to evacuate the campground, But that’s another story.