„What have the Romans ever done for us?“
That is a really classy, classic bike. I know what you mean about the effort on the bars, when I ride my Scrambler after being on my other bikes for a while, I have to be attentive to stay in lane or on my side.
I understand using generations as an aid to statisticians dividing populations but using generations to generalise behaviour is weaponising age in a way that shouldn’t happen (as a test swap out a generation comment for a body type or your homophobic slang of choice)
Haha still a fair question and some nice answers. And you def should plan a trip too.
It’s a fair question and you don’t say what your bike is so it’s hard to answer, but in general your (relatively modern) bike is tougher than you think and it will be fine. I’d say practise your slow speed and tight turns in a car park - that will help going up. Coming down, use engine and both brakes to slow before the corner - take it easy (especially if it’s damp/cold) and you will enjoy it. And you will be fine. Source: rides in mountains sometimes. 
A shake down ride to make sure everything is in order. Needs a little more air in the forks, and I need to add lights to my list, otherwise all good.
I have a 5l kriega tank bag and a mount for each bike. It’s a good size for the important stuff. Straps are a bit fiddly but it’s useful.
You can do a lot with Rok Straps and a decathlon waterproof bag.
Cool cafe Also you are doing all this without suspension. I started a tour in Italy last year on my hardtail, but it was a bit punishing as the trails looked like yours. I’m going back in June. It taking my fully in touring-bike mode (tent on the front, drybag strapped below the saddle bag. I think it’ll be ok)( I just have to carry less)
Good call for the early rest day, and kudos for fessing up to the badass photo (although in truth the whole journey and all the photos are actually badass). Nice report. Please write more while you wait for food - it feels like one of my trips and the story is almost as good as being there. Except the beers.