- Written by Heather Nurfer, Art by Brenda Hickey, Coloring by Heather Breckle
Fluttershy is afraid to return a fish, Gil, back to the ocean after she helped nurse it back to health, and the rest of her friends and Spike decide to help her out, making it a beach trip to Horseshoe Bay. While the others enjoy the fun in the sun, Fluttershy lollies over releasing Gil, until the sudden arrival of a pirate ship washes ashore and sends Gil into the ocean. The ship's captain, Hoofbeard, disembarks and asks the mares about any ready stallions for joining his crew to search for treasure on the mysterious Gallopinghost Islands. Rainbow Dash and the others assert they are just as capable, and Fluttershy is quick to join, hoping to find Gil. Twilight remains skeptical until Hoofbeard points out that only a skilled navigator will be able to meet the challenge of getting to Gallopinghost to find a valuable jewel via the Map of the Wandering X, a challenge Twilight quickly accepts.
Their first stop is an old sea town, where Hoofbeard tells the Mane 7 that they need to recover the map to Gallopinghost from his old crew that abandoned him. With Fluttershy strangely wanting to stay behind, and Spike acting as Hoofbeard's "parrot", AJ offers to stay behind, suspicious of Hoofbeard's motivation, particularly his need to unload numerous messages in bottles into the ocean. While Fluttershy secretly finds and recovers Gil, AJ makes a special pineapple juice truth serum and gets Hoofbeard to explain himself: that the failure to get the treasure at Gallopinghost will be a one-way ticket to Wavy Jones' locker.
The other four head to an old bar and find Hoofbeard's crew. Rainbow Dash is immediately enraptured by real pirates, and gets the group into a scuffle, and the pirates briefly toy with the idea of holding Princess Twilight for ransom before she puts them in their place with her magic. Foiled, the crew explain that when they were part of Hoofbeard's crew, the "X" on the map literally wandered, and Hoofbeard was driven mad to keep chasing it down. The crew thus stole the map, and because it was indestructible, threw it in the pit of a nearby creature. One of the crew leads them there, revealing the map now guarded by a ghost of a giant crab.
It turns out the crab is really just a scavenger that drank too many energy colas, and with Pinkie's friendly help, they calm the beast, long enough to get the map and discover one of Hoofbeard's messages that appear to to vow to meet an unknown agent in the future. Back on the ship, they find Hoofbeard remains secretive of his goals, and worry more when, following the map, they leave themselves in the area of the sea without wind, stranding them. Twilight convinces the Mane 6 mutiny and take control of the ship, with the pegasi helping to provide wind to get them back to Ponyville. Fluttershy talks to Hoofbeard in the brig, finding that he is more despondent than angry.
Suddenly, the ship is attacked, and the ponies find themselves being attacked by mermares who have been slighted by Hoofbeard's ways before. Fluttershy quickly realizes that just as desperate as she was to find Gil, Hoofbeard was to find these mermares, and they all come to find that the treasured "jewel" is really a mermare named Jewel that Hoofbeard loves and tried to take from the mermares, and hence why the "X" wandered on the map and the numerous letters-in-bottles he wrote. Fluttershy demonstrates that nopony can make anyone stay with anypony else by releasing Gil, and the mermares agree to allow Hoofbeard to travel with them on his ship. Twilight uses her magic to give Hoofbeard gills and fins so he can be with Jewel, and the mermares provide the Mane 6 a mantahawk to helps them get back home.
These issues provide examples of:
- Artistic License Biology: Pineapples do not grow on palm-like trees (the plant is short, which the fruit is pulled from its top). However, this does give Applejack some fruit-bucking to do to make delicious drinks for Rarity. Although it wasn't really clarified whether Applejack got the pineapples from the trees or not. We only see her climb up a tree to give Rarity her drinks while carrying one pineapple.
- Aside Glance: Rarity does this at one point to lampshade Rainbow Dash's grasp of pirate-talk.Rarity: Well, I'll be-Our Dashie can speak pirate!
- Authority Equals Asskicking: When the pirates threaten to take Princess Twilight for ransom, a few good zaps of her magic to their flanks puts them in place and makes them agree to help out.
- Beach Episode: It starts off this way until Hoofbeard shows up.
- Beware the Nice Ones: During Fluttershy's reluctance to return Gil, one frame briefly returns her to an obsessive personality:Fluttershy: ...And I'm keeping you with me forever or until I'm sure you don't need need me anymore, whichever comes first.
- Blade Brake: Rainbow Dash makes her way down the sail this way. She doesn't stick the landing, though.
- Break the Haughty: Just a bit; with everything settled, Hoofbeard finally mentions Rainbow Dash by name, which she takes in pride. Until he mentions she was the second-greatest captain after himself and taking back his captain's hat.
- Call-Back: In the second issue there's a few significant nods back to the storybook Under the Sparkling Sea. Mermares and a Mantahawk appear and Twilight is shown to use the same gill/fin spell she learned in that book.
- Chekhov's Gun: Applejack uses the pineapple juice truth serum on Hoofbeard to find out exactly what it is he's after.
- Continuity Nod: This is the first appearance of Princess Twilight Sparkle in the IDW comics, affirming Word of God that all subsequent issues will be considered post-Season 3. Twilight even uses her status to try to peacefully work a deal with the pirates, and when they refuse, she kicks their flanks. (The first issue's release was a few days before the premiere of Season 4 in the United States).
- Cutlass Between the Teeth: This is more out of necessity than any coolness factor though, since as ponies, they lack hands necessary to wield swords normally. Rarity and Twilight, however, can use telekinesis to wield theirs.
- Doppelgänger: When the crew reach the Gallopinghost Islands, they encounter Hoofbeard's old crew. There are also ponies who bear a striking resemblance to the CMC as well as Granny Smith and Big Macintosh.
- Dressed to Plunder: Hoofbeard and his crew, obviously, but the Mane 6 all get into pirate-themed apparel once they join Hoofbeard. Even Spike dons an eyepatch despite playing parrot.
- Drunk on Malts: Fluttershy can't hold her pineapple juice.
- Exactly What It Says on the Tin: The Map of the Wandering X literally has a wandering "X", which is enchanted to track the migration patterns of merponies.
- Fair Play Whodunit: The signs that Hoofbeard was looking for Jewel the mermare were there for the reader to spot and put together - the wandering "x" on a map, the crew claiming their Captain had been driven crazy, the numerous messages in bottles sent out, and Hoofbeard's vague notion of what the treasure would be.
- Fence Painting: Hoofbeard convinces Twilight to join the others by describing the difficult task of navigating to the Gallopinghost Islands, stroking her ego a bit to assert only the brightest of navigators can get them there.
- Funny Background Event: Prior to Hoofbeard's arrival, Rainbow is throwing a boomerang to herself. When Hoofbeard arrives, after she's thrown it, Rainbow is in awe of Hoofbeard — and barely notices when the boomerang smacks her in the back of the head.
- Giant Enemy Crab: A ghostly one at that. It guards the map. The "ghost" part turns out to be too much energy drinks.
- Horsemen of the Apocalypse: When challenged by the pirate crew to prove who they are, Rainbow Dash calls herself, Twilight, Rarity, and Pinkie the "four ponies of the apocalypse". Pinkie later sings a song about it.
- Hurricane of Excuses: Fluttershy tries to reason with the others as to why she can't release her fish Gil back to the sea.
- Identical Stranger: A couple of the ponies in the bar eerily resemble Granny Smith, Big Mac, and the CMC.
- Interspecies Romance: It turns out Hoofbeard's "treasure" was a mermare named Jewel, and the two had fallen in love.
- In Vino Veritas: The pineapple juice. It's heavily implied to be alcoholic.
- Jumped at the Call: Hoofbeard barely manages to introduce himself before Rainbow Dash volunteers the Mane 6 to become his crew.
- Made of Indestructium: The Map of the Wandering X cannot be destroyed or lost, so Hoofbeard's crew stole it and threw it down a hole guarded by a Giant Enemy Crab.
- Mythology Gag: One of the crab's treasures appears to be a G1 pony.
- Our Hippocamps Are Different: The story's second half prominently features mermares, equines with fish scales and fins for tails and forelimbs.
- Pirate: The heroes appear to be taking this as Type 2.
- Pirate Booty: The girls believe Hoofbeard is searching for a valuable jewel. He is in fact searching for a mermare named Jewel.
- Pirate Parrot: Spike gets to take on this role. Hoofbeard even insists on keeping him nearby since he looks more "regal" with Spike there.
- Plot Parallel: Hoofbeard's desire to be with Jewel mirrors Fluttershy's own desire to keep Gil with her, and when she realizes this, provides the inspiration to revolve the troubles of the Hoofbeard/Jewel plot.
- Punctuated! For! Emphasis!: Rainbow Dash gets a few of these, finally being around real-life pirates.
- Ragtag Bunch of Misfits: And they're entirely self aware of it.Pirate: Look at the lot of ya — a princess, a fancy frock, a pink thing, and a wannabe pirate — it's the only crew he could get.
- Sarashi: Rainbow Dash has cloth wraps on her chest and arms.
- Swashbuckler: Rainbow Dash proves surprisingly adept at swordfighting when she confronts pirates about the Map of the Wandering X, complete with a Chandelier Swing.Rainbow Dash: Hey, yoou guuuys!!
- Take That!: Rainbow Dash takes a shot at energy drinks in #14.
- Talk Like a Pirate: Obviously, but Rainbow Dash is surprisingly competent at it. Fluttershy, on the other hand, not so much.Fluttershy: Um, silver me tubers! Is that right?
- Talking Is a Free Action: Just like Roronoa Zoro, Rainbow Dash has no trouble speaking while holding a sword in her mouth. None of the ponies can understand Pinkie, though.
- Toilet Humor: As Twilight and the pegasi are about to try to help the ship catch a breeze...Rainbow Dash: Cool! I'll make the wind!
Pinkie Pie: He-he! She sometimes breaks it too!
- Trailers Always Spoil: See those mermares on the covers of both issues? Yeah, no prizes for guessing what Hoofbeard is really chasing after.
- Treasure Map: Known as the Map of the Wandering X; Hoofbeard is after it.
- Truth Serum: The pineapple juice. It's heavily implied to be alcoholic.
- Umbrella Drink: In issue #13, Rarity professes twice her love for "little umbrella drinks" before being seen drinking one (with three umbrellas) on the beach.
- Wingding Eyes: Upon learning Twilight is a princess, Hoofbeard's old crew immediately agree to help with dollar signs in their eyes.