I vaguely recall something about a ship he served on between the Farragut and Enterprise, but can't think of the name. It wouldn't have been mentioned on-screen, though, so maybe I'm thinking of something I read in The Making of Star Trek
But I'm guessing that at one time he must surely have captained sailboats on Earth, or at least in his bathtub.
In "Court Martial", it said Ensign Kirk logged Finney's mistake while serving on the USS Republic. The Farragut, when he was a Lieutenant, was mentioned in "Obsession".
Thanks; I'd forgotten about the events in "Court Martial."
Every officer under Picard was shown to be unbelievably talented, and if their goals were Captaincy, they would have all been plucked. Instead, you've got characters like Riker who remains at the Commander rank for 15 years, or Data who remains at LtCmdr rank for nearly 20. La Forge is a quick-starter who is promoted to Lt Cmdr in 9 years, but remains at that rank for at least the next 14 years (canonically, at least).
All of these characters who ascend to a certain rank and then stay put are essentially roadblocks in the careers of young officers who hope to rise rapidly.
Perhaps they are all related to Harry Kim.
Actually, I think Riker took a look around to see how many Captains were being killed in action and decided he'd rather stay put, thankyouverymuch.
Something nobody has mentioned yet: Kirk participated in a ground assignment among Tyree's people some years before he took command of the Enterprise. Which ships was he between at the time? Or was this an extended landing party assignment? It's been ages since I've seen the episode, and just can't remember.
Also: Kirk states in "The Deadly Years" that he is 34 years old. Was this in the 2nd or 3rd season?