This is slightly cheating—unlike “Shore Leave,” this iconic original series episode isn’t entirely about the crew taking a break. Kirk is actually on a diplomatic mission when he finds that the Federation undersectretary at station K-7 to deal with a territory dispute with the Klingons is willing to allow him to give his crew shore leave aboard the station.
Naturally, Tribble outbreak in the main plot aside, this also leads to shenanigans, when Scotty, Chekov, and a bunch of other Enterprise crew get into a bar brawl with some Klingons also having shore leave on the station. Hey, some vacations are rowdy! Bonus opportunity: Deep Space Nine’s wonderful anniversary homage, “Trials and Tribble-ations,” gives us some extra insight into this aforementioned brawl thanks to a shenanigan even more fun than shore leave to Star Trek: time travel.