A couple successes: Rode coast-to-coast with my then-10 year old daughter on a Santana steel frame tandem pulling a BOB trailer with our gear. Took 80-days and was a great bonding experience.
Several years later, on a Co-Motion triplet completed the "Hotter n' Hell Hundred" with my then 13-year old and 10-year old daughters as stokers. It gave a great sense of accomplishment to all three of us.