wearing cycling shorts. An important detail is getting your butt ready to spend 8 hrs in the saddle.
As someone else has pointed out, this is a big thing. I can happily spend 12 hours in the saddle on one ride with no pain the backside.
Going from 10 hrs a week to 12 hrs at one time is a big jump. Whenever I exceed my normal mileage or saddle time by a factor of two, I start to get small skin wounds, or abrasions. It takes time and conditioning for many people to go longer than double or triple the saddle time all at once and then be able to do it again the next day. Often in multi day rides they report doing well on day one or most of day two.
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The physical effort is one thing. I felt fine but tired after my first 140 mile ride. The second long ride (150 miles) I felt absolutely shattered, barely able to cycle the last few miles home. But you should consider the mental side of it as well. All that time alone on a bike can do strange things to your brain!
Yeah, I think it would be best done with a partner. In addition learn to time your peaks and do those rides when you're on the upswing. Timing and tapering.
