... This is all gearing up to cycle touring with him in a few years
Just a thought? The cycle touring bit is possibly the easy way in?
I took a 12-year-old across the Pennines from Skipton to wild camp somewhere in the Forest of Bowland. Yeah, I know - that's the easy way. But coming home again, we went by Nelson and Widdup to Hebden Bridge
. [We took the train Leeds-Skipton, and Hebden Bridge-Leeds.]
When he was 14, we rode 200 miles to Edinburgh - and he proved to be far and away the tougher, and immeasurably more resilient, cyclist between us two.
However ... would I have let him on the road in Leeds on his own at that time? Nope - except in the very quiet residential streets around his home. [Actually - would I let him on the road alone now, at 25? Not from choice, but some silly DVLA dogsbody has given him a driving licence - be warned
.]
I herded the gaggle of my kids (3-4 of 'em) cycle-camping - across the N York Moors; the Yorkshire Dales; Derby-to-Glossop-across-the-Pennines-to-bypass-Wakefield-and-back-to-Leeds; Alnmouth to Berwick; and all sorts of other shorter day-trips, in the sticks. The first trip? My youngest was 6, I think.
Bottom line - they learned SO much about enjoying the freedom of cycling for what it can be, about roadcraft, about reading traffic, and (damn it!) about repairing punctures on the road. Cycling on their own on city streets in Leeds (or for two of them, in Sheffield where they were students) ... came later?
Not a recommendation!
Just how it turned out for us ... with no planning, beyond careful preparation and route-planning for the next challenge. And all four kids are still cycling, in their different ways
.