First boat was a 00 Trophy 23'
Went to a 50' 2002 Viking

- sold in 2006 because our captain kept taking it out of his own free time and charging people for private charters (heh, we always would swear that it burnt gas while it was in its slip). After that my father swore off hiring crews, and insisted we could maneuver the boat by ourselves. It only took 2 nice gashes in a matter of a month before we sold it.
Downsized to a 2006 Grady 33 Express - which was sold last year after only using it maybe 8 times.