Several days of blind sailing have passed since Twilight and her friends have last seen Korsan’s ship. Now with a fully cloudy sky above their heads, the ten meet up at the galley to discuss their situation.

“That’s it,” Rainbow Dash complains, “we lost Korsan.”

“Don’t be so glum,” Applejack replies, “We’ll find Thieves’ Hold in time. Right Twilight? You know where we’re going directly to it.”

“Well…” Twilight hesitantly answers, “To be honest, I only know the general area of Thieves’ Hold.”

“And we are heading to that general direction right?”

“Well… I don’t know.”

“Are you saying we’re lost?”

“Everything looks the same! We’re surrounded by ocean. Despite all of my navigational gear, the ocean will still be the ocean.”

“Then why don’t we just go in one direction until we hit land?” Rarity asks.

“That might not be a good idea. What if we sail into the Ley Lines again or something equally as dangerous?”

Fluttershy replies, “Yeah, maybe we shouldn’t take the risk.”

“We’re going to have to take some risk in order to get anywhere.” Rarity retorts.

“Maybe we all just need to calm down and think about this more.” Spike suggests.

“If only some old pony with a raft came along who understood this ocean like the back of his hoof and helped us.” Pinkie says.

“Now that’s just ridiculous,” Rainbow retorts, “now we’ve been through a lot of weird things, but this might take the cake.”

“Uh… Dashy,” Fluttershy mumbles.

“What?”

“I wouldn’t tempt fate.”

“What fate? The chances of something like that happening are zilch.” A subtle knocking at the port side of the hull is then heard below the mares. “What’s that?”

“Let’s go check it out.” Applejack proclaims, “You three fillies stay in here.” Quickly, the six older mares and Spike charge out to the main deck and look over the side where the knocking is coming from. To their surprise, they see a small wooden platform with a large chest and a small sail in the middle of it. Even more surprising, they see an old Earth pony stallion with a very desaturated green coat of fur and a very white and short mane and tail hitting their ship with a wooden staff.

“Excuse me,” Rainbow Dash calls down to the stranger, “can we help you?”

“Darn kids,” the old stallion shouts in a withered voice, “keep your darn noise down. I’m trying to take a nap here.”

“We weren’t making all that much noise-”

“That’s what they all say these days. Listening to that mess of racket they call music.”

“Are you lost sir?” Twilight replies.

“Do I look lost?”

“Uh…”

“If anything, you whippersnappers are lost. What were you kids doing messing around in the Ley Lines?”

“We were following a pirate named Korsan. Have you seen him?”

“He drives this massive floating pirate ship with black sails,” Dash adds, “you can’t miss it.”

“That’s a boat?” The old pony mutters, “I thought it was that Discord villain stirring up trouble.”

“Discord?” Fluttershy asks, “You know him?”

“Everypony does, he’s bringing everything to chaos. You kids would know if your faces weren’t into all of those magazines.”

“How old are you even?” Dash rudely asks, having grown tired of his indirect insults.

“That’s none of your business. Rude kids…”

“Sorry for my friend’s disrespect,” Applejack responds, “you are right. This generation’s going to the dogs.”

“You said it. At least somepony’s wise enough around here,”

“Yep,”

“Applejack,” Twilight whispers to her, “What are you doing?”

“I’m trying to get on his good side by using some words that Granny Smith says in her sleep. He knows those Ley Lines we were in, maybe he can help us get to Thieves’ Hold.”

“Now if you’ll excuse me,” the stallion speaks, “I’m going back to sleep.”

“Actually, can we use your help?”

“What is it?”

“We’re trying to get to a place called Thieves’ Hold and-”

“Thieves’ Hold?!”

“Yeah, do you know where it is?”

“I do, but I’m not taking you there.”

“Why?”

“Thieves’ Hold, you will never find a more wretched hive of scum and villainy. You kids must be cautious out here at sea. I have a bounty put on my head at that place, ten bits!”

“Just ten?” Rainbow interrupts.

“Darn kid, quit interrupting me!”

“We’re adults by the way.”

“Not when I’m through with you.”

“What does that even mean?”

“Just watch and I’ll take my stick here and put it up-”

“Sorry,” Applejack interjects before the stallion could get into the details of his threat, “but it’s a very urgent matter. We’re lost and we need your help sir.”

“…”

“Please. We won’t let anything bad happen to you when we get to Thieves’ Hold.”

“…Fine. Take me up to your steering.”

“Thank you mister, uh… What’s your name?”

“Craig Y’ol Timber, just call me Craig.” Gently, Twilight grabs the small log raft with her telekinetic magic and hovers it over to the poop deck with her and the others following. Upon landing, Craig slowly walks off his raft with his cane in hoof and approaches the girls walking up the stairs to him. As Rainbow Dash draws within a metre of him, Craig quickly hits her on the head with the end of his cane.

“Ow!” Rainbow cries out, backing away and rubbing her head after the hit, “What was that for?”

“I don’t like you lot of kids. Dying your hair all sorts of whacky and not brushing, listening to that garbage yous call music, not respecting your elders,”

“First off, this is my natural mane and tail. Second, maybe I would respect you if you’d quit being an old fart that smells like-” Before she can finish she is stuck again by the end of the stick. “Stop it!”

“Darn kid. Now where’s the rudder?”

“Right here sir,” Twilight answers, walking towards the wooden steering wheel.

“That’s no rudder, that looks like some oversized toy. Where are the oars even on this thing?”

“No, this controls the rudder at the back of this ship. And we don’t need oars, it’s all wind powered.”

“You don’t say? That sounds like some newfangled technology.”

“It’s been around for centuries.”

“How do you steer it?”

“Simple, you turn it left to go left and right to go right. I’ll get this thing moving and you can point us in the right direction. Come on Fluttershy, Rainbow Dash. Rainbow Dash?” Looking back towards Craig positioning himself at the wheel, she sees Rainbow Dash blowing a raspberry behind him. However, Dash’s taunt is promptly interrupted by the old stallion grabbing his stick from the ground and bonking her head again.

“Blasted kids…”

“Come on Rainbow, don’t make it worse.” A small growling can be heard from the blue pegasus as she flies up behind the white sails and begins flapping her wings. With the three winged ponies pushing wind into the sails, the galleon starts to move forward quickly and dart across the sea.

“Whoa! Slow down! We’re about to miss the turn.”

“What?” Applejack asks in confusion, “Thieves’ Hold’s a fair distance away. You have plenty of time to aim this thing strait at it.”

“We’re not going the long way. I may not be in my prime, but I still know a thing or two about speed. Also, can you hit that Rainblow Darn kid with my stick?”

“Where are you going?” Rarity worryingly asks.

“Open your eyes, we’re taking a shortcut.”

“A what?” The three mares with Craig look around the sails and over the bow to see a large whirlpool ahead of them, swirling violently as waves wash over onto the deck. “You mean that spiraling vortex of death?!”

“Don’t be ridiculous. I’ve done this plenty of times.”

“Are you sure it’s safe?” Applejack nervously questions the driver.

“Sure as that Crystal Empire garbage is nothing more than a myth.”

“Oh dear…” Spike groans.

“What? It is.”

“Adventure is out there!” Pinkie screams in excitement as the ship enters into the circling water.

“Hey you flying ponies up there, yous might want to hang onto something!”

“What?” Twilight, Rainbow Dash, and Fluttershy ask, oblivious to what’s going on. However, as the galleon starts to dive down to the black hole of the whirlpool, the three are able to see over the top of the sail and see the spiraling water in front of them. “What the-”

“Please keep your hooves, legs, manes, and tails inside the boat at all times!” Frantically, the three fliers dart down to the deck and clutch onto the wooden floor as the entire ship plummets into the abyss. Inside the center of the whirlpool and below the seafloor, the large galleon plummets into a large underground cavern. Landing on a river facing towards the flow of water, the ship pounces forwards into the dark caverns with most of the mares and Spike onboard screaming in terror while the three fillies and Pinkie are instead screaming in joy.

“What is this?!” Applejack cries in panic.

“Super-fast rivers that flow through an underground system carved out by erosion and pressure. Very round as well. After traveling through these throughout my years at sea, I can go anywhere in the world as I please. Duck,”

“Wha-” A large stone spike then appears in the darkness poking from the wall and is heading towards the orange mare. Applejack fanatically ducks as it swipes over her body and shattering the edge railing at her side.

“Hm, this ship might be too big. Oh well.” As the vessel continues to speedily careen through the pitch black cave, more stalagmites and stalactites are rammed into, breaking apart the galleon bit by bit.

“I regret everything!” Rainbow Dash squeals as she’s tightly hugging Fluttershy, “I regret everything I have ever done! I should’ve never tempted fate!”

“Turn it down ya noisy brat, I’m trying to concentrate.” With a sudden turn of the wheel, the boat sharply turns left, grinding it’s keel against the side of the unseen cavern walls as if defying gravity.

“I hope you enjoy the loopy-loops.”

“The what?!” With another jerk of the steering, the ship then swings over to the other side of the tube-like cave before flipping upside down and grinding against the ceiling of the cave. Eventually however, gravity makes itself known once more as the ship completes the spiral and lands back into the raging current at the bottom. “All I see is black and my life flashing before my eyes!”

“Quit your crying you pansy. Just a few more minutes,” Several more minutes pass of the ship darting around in pitch black before being suddenly slowed down by an unseen force. “Almost there, hold your breath.” With Twilight practically glued to the middle mast of the ship, she looks ahead and sees a small light beaming down from ahead, an exit. As they speedily draw closer, the purple alicorn sees that they’re fighting against the current now and that the exit is surrounded by a large waterfall.

How will we able to get out? Twilight rapidly thinks to herself, if it’s a whirlpool that got us in here, then it’s going to be another at this point.

“Nearly there, hopefully this thing floats like my raft.” As the tip of the bowsprit then pieces the edge of the thick waterfall, the entire front of the vessel jerks down a small bit, but still pushes forwards. Slowly, the ship’s entire front is bathed in water and starts to lift upwards instead. With more and more of the large watercraft entering the thick column of rushing water, the more it leans upwards towards the surface, smacking the ponies onboard with tons of water continuously, yet they continue to hold on with all of their might. Eventually, the entire ship becomes entirely enclosed in water and starts to slowly move upwards against the waterfall and towards the sunlit surface. The onboard crew holds their breath for as long as they can whilst still holding onto the boat in any way conceivable to them. A minute passes before the galleon bursts from the water with an enormous splash and resumes its sailing position on the surface. The mares, Craig, and Spike promptly gasp out for air and relief from their fast-paced travel through the caves, not noticing how the cloud-covered sky has grown increasingly thicker and darker.

“Never again,” Dash whimpers, still tightly clutching onto Fluttershy.

”Heh,” Rarity giggles from the poop deck before coughing, “this maybe the first and last time I’ve seen you not want to go fast.”

“Oh bug off, you were screaming your head off the entire time.”

“And you weren’t?”

“Can somepony please remove Dash off of me,” Fluttershy groans as the large weight continues to tightly hold on her side, “she’s getting heavy.”

“I feel sick,” Spike moans with his face planted into the wet deck.

“That was awesome!” Pinkie loudly cheers, making the old stallion beside her cringe. “Let’s do it again!”

“Yeah!” The voices of the three fillies call out from below.

“No, we’re not doing it again.” Twilight stridently replies, “I need to check around and see how much damage has been done. From first glances alone, Princess Celestia’s going to be furious.”

“She won’t be if she’s still dating that mutant guard.” Craig Y’ol Timber responds as he slowly descends from the wheel.

“What are you-” Applejack responds before realizing what the answer will most likely be, “Never mind. Craig, how come nopony’s ever known about that cave system other than you?”

“Meh, most ponies actively avoid the whirlpools. And those who do, well, you know the answer.”

“I under-”

“They die.”

“…stand…”

“Big, red, dead,”

“Well,” Twilight yells out, circling around the ship in the air, “A snapped mast, most of our remaining sails torn, large holes in the upperparts of the hull, two thirds of our cannons gone, a missing keel, a busted rudder, the bowsprit broken halfway through, most of the paint competently gone, nearly all of the railing broken, and I don’t even want to know how much has broken inside. Thieves’ Hold better be real close.”

“Behold, Thieves’ Hold. Tartarus on Earth,” Slowly, everypony on board turns to starboard and sees Thieves’ Hold only a kilometre away from them. Covered in a thin veil of fog, it is a large collection of tall stone stacks clustered together in a vast area of water. Small wooden buildings with faint lights can be seen elevated high above the water, built into the large rock towers, connected to each other by tiny rope bridges swaying in the cold breeze. At sea level at each of the columns of stone is a small ring of sharp rocks jutting out, ready to pierce anything that gets to close, with some rings already having several small, decrepit ships trapped inside them.

“There it is,”

“Well, I better get going, help me get this thing into the water.” Gently, the old Earth pony grabs his staff and hops onto his raft, unscaved after all it has been through.

As Twilight lifts the raft and sends it back down onto the ocean, she speaks, “Thank you Craig, we’ll never forget what you did for us.”

“You’re welcome. Now how about a little push towards the whirlpool?”

“Yes sir.” With a flick of her horn, Craig’s raft immediately starts to drift towards the swirling water behind the galleon. Pinkie Pie, Fluttershy, Applejack, Spike, Twilight, and Rarity walk towards the railless edge of the deck and wave goodbye. Rainbow Dash however flies down and hovers over the raft, rudely blowing a raspberry at Craig, only to get hit in the air by his staff being thrown at her and immediately retreat back to the safety of her ship.

“Darn kid!” Soon, the old stallion’s raft sinks down into the black hole of the whirlwind, leaving the team to enter Thieves’ Hold as the night soon arrives.