+1, to this approach. We started with a trail-a-bike when our first son was 4, nice for an hr or so. Not comfortable for either rider after a couple hrs. We found a lightly used tandem when he was 7, did lots of local riding. Then our first tour was the 5 Boro - which went well - but. It was a single day ride. Then we did a week long sagged tour, it is really hard for an 8 yo to sit on a bike that length of time. We stopped every hour, walked a few minutes, explored our surroundings. He went solo after a year on the tandem, he did not like the scenery from the navtgator's seat. The ride at that age, is really your kid's ride. The oldest is now in his twenties and still riding. Our soon to be 15 yo son has done 7 tours with us and looking forward to next summer's tour.