Star Trek's Best Shore Leave Episodes

You can’t have this list without the original shore leave episode! When the knackered Enterprise crew heads to an unknown planet to catalog flora, Kirk decides to give his crew a chance take a rest... only for them all to of course get high on some of that aforementioned flora, which affects their minds and makes imaginations become distressingly real. Oh, and Doctor McCoy briefly seemingly dies but then comes back alive and with two attractive women dangling off each arm at the end of the episode. It’s very silly.

Sure, it just aired this week, but Strange New Worlds’ homage to shore leave episodes is a lot a fun. The campy main plot of Spock and T’Pring’s attempt at getting to know each other accidentally leading to an awkward body swap is a delight, but the real joys are the snippets of crew life beyond the Enterprise we get see here—especially for La’an and Number One, two stick-in-the-mud rule lovers who try to learn how to have fun.

The NX-01 crew gives us something of an origin story for the pleasure planet Risa—a name you will be seeing again in this list!—as the Enterprise crew draws lots for which half of the ship is going to get to go down and enjoy a vacation. Those that do go there however find that not everything is as relaxing as they dreamed it to be. Kidnappings, rock-climbing accidents, secret agents... turns out Risa’s got a lot more than just nice beaches.

Voyager is a weird show for shore leave—the crew is exploring a previously unknown quadrant of space and trying to get home, so they can’t really just kick their feet up and relax on a nice planet somewhere. Instead, the series gave its crew digital hideways in the form of several holodeck programs throughout the show. Early on we had Chez Sandrine, a French pool bar, and we eventually got Neelix’s take on the Paxau Resort, a tropical hotel. But perhaps the most infamous and fun of all is the short lived 19th-century Irish village of Fair Haven.

I’ve previously said that “Fair Haven” was a bad episode, because Captain Janeway gets very horny for one of the holo-townspeople and alters his subroutines to be the ideal paramour, including the iconic line of her telling the holodeck to “delete the wife,” but I have grown and matured as a Star Trek fan since then, and can happily declare: this is extremely good, actually.

Not all shore leave episodes are a gag, however—sometimes the catharsis is much more serious and emotional instead of “I’m a Starfleet officer who needs a vacation, oh no!”

Picard’s homecoming in La Barre after his assimilation as Locutus in “Family” is one such serious example of times we got to see our heroes step aside from their job for rest. It might not feature the outward fun many of the other episodes mentioned here do, but it’s an important and emotional moment for the character that shines an alternate spotlight on what these kinds of episodes can be.

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.

There are maybe two ultimate shore leave Star Trek episodes: one of them is, of course, “Shore Leave,” the other is this TNG icon. This time, it’s Picard visiting Risa, to settle down for a break with a good book and very little clothing, only to find himself thrust into an adventure of archaeological drama, Ferengi double dealings, and a liaison with the fantastic con artist/artifact hunter/superflirt that is Vash, played to perfection by Jennifer Hetrick. Picard may not have the relaxing time he thought he might, but we get to have a lot of fun.