I don't see any reason it shouldn't work!
Never thought about doing that...EXCEPT....don't you have to key in to talk?
The ones we used to carry at the Poboy Store were simpler, but we had problems with durability issues with the Dixie cups and string tangling....so we discontinued them.

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Yeah, I think some of them have a voice activation feature, but I would be willing to bet it doesn't work that well. I think pushing a button to talk would be manageable if there isn't a way around it. Just have to put the handset in a pocket or something you can reach with your hands while driving.
The main thing Im thinking will be a problem is volume. I don't know if those headsets would get nearly loud enough to be heard with the engines running, wind, etc. I don't need it to be super loud, but it would sure be nice to not have to stop, kill the engine, take off helmets, etc. just to tell my son to stay behind me or wait up for me, or things like that.
Guess Ill just have to try it and see. I'll let yall know if it works worth a crap.