Well, if you look at my mileage report, what happened is that I basically did the equivalent of 2 evening rides, then hit 80 or 90 the third day. The fourth day was actually longer, because I added about 15 miles more when I lost some keys. So yeah ease into it. But that could mean do a 40 and a 40 on thrus fri, then take off on saturday. The body will up the strength very quickly. But where it gets tricky is what if you make 97.5 miles. No problem for me, because I wasn't headed anywhere that day. What if you feel like 100, but I take it you are going with your son? So really it is a problem to the second order of magnitude: Anything that can go wrong twice. I did have fit issues because it was a brand new bike, with a brand new Brooks. I had broken the Brooks in for half an hour, so that was good to go. But I had some knee pain. The moment I felt that I stopped and tweaked my postion. Plus with the injuries I had to rebuilt my pedals several times. And actually on the first few days, I had a situation where my big toe was stubbing the end of my sandal, so I had lost nerve sensation in that toe, which didn't return until about a month after the ride was over. Again, every time, I stopped and sorted the problem out right away. The first two days of 40 miles weren't some magic number, they were pretty much what I felt like doing. So then, with someone else, I would have had all those problems and potential doubts x 2.

Actually a pretty good idea for people doing multi month tours would be to start at your own pace, and then agree to meet at some date give or take, a week or so down the line. A lot of the resentments come into play when stuff gets said in the first few days, as each is driving the other crazy over pace etc...

This is probably just another one of those personal details, but I have never personally found a saddle even in the 100 dollar range, that was comfy day after 80 mile day that wasn't leather. A lot of them are good for 40 a day, but beyond that they are hell for me.