How long is the tour in terms of days?
For most tours of a week or longer, I have a budget, not a schedule. In other words, I wake up in the morning and have a rough assessment of the possibilities for that day. It might be going 45 miles, 65 miles, 95 miles or staying where I am. Depending on the weather (including wind) and other factors, I'll figure it out as I go along. If that headwind kicked in, I might take what was I expected to be a 65-mile day and turn it into a 45 mile. On other hand if everything is going extra well and I have a tailwind, the 65 miles might turn into 95 miles.
Sometimes there might be a synchronization point (e.g. cycling through a sparsely populated area, really want to get to a town), at which point I'll push a little harder if necessary - but that isn't the usual case. A good example is recent trip I took over Christmas break in South Texas:
Brownsville to Austin I drove to Brownsville and a direct route back to Austin would have been ~330 miles. I took it day by day and ended up swinging further west to go by way of Laredo and make it 484 miles instead. If the weather hadn't looked unfavorable [strong NW wind], I might have swung further west via Eagle Pass, but instead that day went NE to avoid that wind. By time I got to San Antonio, a cold front with temperatures near freezing but more importantly possibility of icy roads came through, so stayed in San Antonio for two days before cycling back.
On even longer trips, I'll have even more flexibility to adjust and keep my overall budget realistic so I don't get into a trap where I'm feeling more behind and somehow "behind schedule". The only situations where this sortof applies is in the shortest tours, e.g. on a weekend out and back - where if it looks good on Saturday, I might have headwinds on Sunday. However, even then for a lot of the country you can predict this weather by Friday and adjust accordingly.