When did Kirk really violate the PD? Maybe with Vaal and Landru, but that's a maybe.
I really don't think either of those qualify as Prime Directive violations(at least by 23rd century standards). Both posed dangers to orbital traffic, Kirk tried to leave when it became obvious they weren't welcomed on Gamma Trianguli VI yet was stopped by Vaal.
Did any of the 24th century shows put their crews in a similar situation?