I remember the day I got the balls to ask my dad this exact question.

I had been trailering since 14yr old, operated heavy machinery since 12 and grew up with quads and dirt bikes. My dad wasn't scared of my judgement but the judgement of others. My first trip wasn't a long weekend either. It was a day trip but I was 18 not 23.

If your kids have the same respect I had (sounds like maybe more) they will do great and keep their friends in line also. Mechanical problems happen. Are they trained enough to wrench on some things with dad on the phone (video calls did not exist in my day)? Could they change a prop if needed and do you have a spare? Could they change a trailer tire? Basic mechanic skills and a socket set goes a long way.

These are things they will remember forever. I know I still do. And 18 with a truck and boat, was a great summer when dad always said yes after I proved myself.