My first solo trip was when I bought my 71 hondo flat w/ a 400 SBC in it...Went out there, broke the boat, fixed the boat, broke the boat, fixed the boat...you get the idea. I was 19 at the time. I sold the boat when I got home.
My folks used to give me more and more responsibility as the years went on...first it was sitting on dad's lap steering, then he'd let me drive out of the no wake zones, then drive the boat at speed, then pull skiers...I eventually, I think at 12 or so would take the boat to and from the ramp solo. That was with the old 16' regatta w/ a 100hp evinrude on it. Once pop's bought the Nordic w/ a 200hp merc, I only drove that boat once, and it died on me. I think it's a POS, and I'm scared of it...mostly becuase I don't want to pay to fix a blowed up Merc...
Then I got my Mako and started doing trips with the better half last year after 10 years of being away from the river....It's too much fun to give up again.