I do it a lot as I travel to local bridleways that there's no option to ride to. So I can do 5-10 miles in the box, but then there's nowhere to park when I get there other than on the road. To tack up there would mean either tying up to the box in the road or leaving the box ramp down while I get sorted (box has a side ramp and I can't get to the horses easily through the back door). I don't think that either option is fair to other people on the road, so he travels saddled and with all his fluorescent gear on. He's travelled bridled as well before now, but I find that easy enough to put on out of the way when I arrive, but if he was silly I wouldn't risk it and that would be on before leaving home as well.