I'm not a lad but I cycle with LO in the nicer weather. Just locally, not out into town or anything.
We bought a highbacked padded cycle seat for LO to go in, made sure he's got a sensible helmet and his own little bell so he can ding ding it while were going along....not been out on it in ages though. We had looked at one of those tent things you tow along but they kinda permanantly attach to the frame, need spanners etc to get it on/off and for storage and going out on my own with LO it wasn't ideal.