Have you considered doing the "untethered" thing? I think it involves giving your basal as an injection once a day, and then hooking up the pump to bolus. That way you can unhook the pump whenever you want, but still only have to give one injection a day instead of multiple ones.
What pump are you using? Maybe as he gets older it might be worth looking into one that is waterproof so you can avoid this all together? I think the Animas ping is waterproof (not sure) and I know that's one reason my son loves the Omnipod - he doesn't ever have to unhook it to swim or do anything else. But I know there are lots of considerations when picking a pump - but if this is a major one for you, then waterproof might help.