First one I owned was a strange beast, I believe it was a Springbok, it was a twelve foot aluminium bath tub.  I did some very crazy things in that canoe, and even took three of us on couple of overnight trips with gear and the works. 
When I was around 19, it got stolen, so the insurance company asked me to get a valuation.  I went to the place where I bought it, and he wrote me a note assigning a ridiculously high value to it, with the understanding that I would come back and spend the money at his shop.
I did just that, but now comes the part of my life i like to keep hidden....I bought a kayak.  First time I used it I almost drowned, it had a very small cockpit that made underwater extraction quite difficult.  I can't remember what happened to the kayak, I probably traded it for a case of beer, something I did a lot of in those days.
There's a lot to be said for those old aluminium canoes that many of us cut our teeth on. I'm on the lookout right now for one with the right price, so I can use it as a loaner, since my poly canoe got destroyed by a snow plow.