The sun-and-fun class trip is derailed by a freak storm of volcanic ash that closes down the intended destination. Every other recreational destination is booked solid; instead, Mr. Barkin takes the group to a living-history village where they end up reliving the life (and chores) of the Colonial Period.
Meanwhile, Dr. Drakken has built an undersea lair, and stumbles upon an old treasure chest. He begins acting oddly (in a different way than usual). Wade shows up in person to inform Kim and Ron (their electronics, Kimmunicator included, have been confiscated in the interest of historical accuracy); they take a quick side trip to trash Drakken's new headquarters.
By this point, Drakken has been fully taken over by the ghost of notorious pirate Blackeye Brown. He reclaims his ghost ship and crew, and launches an attack on the village to fulfill Blackeye's vow of vengeance and seize a magic sword that has been kept there since it was taken from him in life.
This episode includes the following tropes:
- 2D Visuals, 3D Effects: A few shots of the clipper ship that Kim, Ron, Monique, Bonnie, & Mr. Barkin's father are on, especially when the ship turns to "Ye other starboard".
- Continuity Nod: Shego insists that only she's allowed to kill Kim.
- Cool Sword: Blackeye's prized sword has magical powers.
- Even Evil Has Standards: Shego is visibly horrified when it looks like the possessed Drakken is about to murder Kim, either because of Shego's ongoing desire to be the one to beat Kim, that it looks like Drakken is going to stab Kim to death and is thus shocked by such a bloody demise, or that she truly doesn't want Kim dead at all.
- Flowery Insults: Drakken, while under Blackeye's possession, calls Kim and Ron "scurvy dogs" much to their confusion.Blackeye!Drakken: "Kim Possible?! Avast, Shego! Capture these scurvy dogs at once!"
Kim: (taken aback) "Scurvy dogs?"
Ron: "Uh... it has a certain offensiveness to it." - Ghost Pirate: Blackeye Brown's crew.
- Heel–Face Turn: After seemingly siding with Blackeye/Drakken, Remy the parrot saves Kim by taking away Blackeye's sword, revealing that he was just pretending to side with the pirates.
- Hypocritical Humor: For all their talk about making Colonial life in Port Mystic Cove Haven as historically accurate as possible, when Blackeye!Drakken launches his attack on the village during the climax, the citizens end up fleeing in their modern day cars. In fact, this is lampshaded by Kim and Ron when, upon seeing the citizens fleeing the village in their cars, Ron says, "So much for historical accuracy..."
- Identical Stranger: Blackeye Brown's picture when Shego is researching him looks almost identical to Drakken, but with a Beard of Evil.
- If I Had a Nickel...: After Drakken gets possessed and their underwater lair starts flooding:
- Immediate Self-Contradiction: When going to the ships, Ron insists that he's going to stick with the high-tech boat after his failure with antiquated methods. Cue the ship being destroyed by Blackeye's flagship, leaving only a sloop at their disposal.Ron: Like I said Kim, if we're going to save this town, we're gonna do it their way.
- Mistreatment-Induced Betrayal: After being locked up in the stockade, Shego refuses to give Blackeye!Drakken his sword back.Shego: After throwing me in the stockade? Yeah, that'd be a "nay". I'm captain now!
- Never Say That Again: After Blackeye!Drakken addresses Shego as "wench", she tells him that doing it again will lead to "a burial at sea". He prudently heeds the warning.
- A Pirate 400 Years Too Late: Dr. Drakken, after he gets possessed by the ghost of Blackeye Brown.
- Pirate Parrot: Remy the village parrot is said to be a direct descendant of Blackeye Brown's parrot, Roger (not "Jolly" Roger). He spends part of the episode as Blackeye!Drakken's parrot. Ultimately Subverted when he turns against Blackeye!Drakken and saves Kim.Remy: (squawk) Remy's a parrot, not a pirate!
- Punctuated! For! Emphasis!: Barkin's "Move! That! Bus!" Also doubles as a Shout-Out to Extreme Makeover: Home Edition.
- Save the Villain: Kim rescues Drakken when he gets tossed into the ocean.
- Screw This, I'm Out of Here!: When the pirates attack Port Mystic Cove Haven, the citizens flee the town in modern day cars.
- Sealed Evil in a Can: Blackeye's spirit is locked inside his long-lost treasure chest until Drakken opens it.
- Strong Family Resemblance: Mr. Barkin's father looks, sounds, and acts just like him (just older).
- Talk Like a Pirate: Drakken starts to do this after being possessed by Blackeye's spirit.
- Tempting Fate: Ron says that at least they'll be away from Mr. Barkin for a week. Seconds later, the students meet Franklin Barkin, Mr. Barkin's father and mayor of the village.
- Took a Level in Badass: Drakken is a much more dangerous villain while being possessed by Blackeye. This is even Invoked by Shego.
- Two-Teacher School: Mr. Barkin's father seems to run pretty much everything in the living-history village, echoing Barkin's omnipresence at Middleton High.
- Weapon Grip Failure: When boarding Blackeye's flagship, Ron, Monique and Barkin Sr. are all armed with swords. Ron accidentally loses his grip on his mid-draw and it goes flying into the water.
- Ye Olde Butcherede Englishe: Franklin Barkin speaks this way.
- Your Other Left: Ron is instructed to turn hard to starboard and then turns the boat the wrong way, but then is instructed to turn to "Ye other starboard."
