Ponies of the Caribbean

by Shukawarioserfi

Rating: teen
Tags: Main 6, Original Character, My Little Pony: Friendship is Magic, Adventure
Length: 2407

The Mane 6 go on a swashbuckling adventure.

Weigh Anchor! In this exciting tale, the mane 6 set sail on the high seas to combat Equestria's latest threat. Is it aliens? Dragons? The dreaded Care-bears from the far east? Read the story and find out.

This story belongs to The Dread Pirate Pinkie

Published 2015-05-29 19:20:01 UTC
Last updated 2015-06-07 00:55:29 UTC

Chapter 1

On the far end of Equestria, just south of the horseshoe bay lies a seedy port town, home to all manners of foul ponies. Vagrants, pickpockets, cutthroats, and of course, pirates. The greasy black tar that held the town together.

It’s name is Trotuga, and its existence had been a blight on Equestria ever since the Dragons started hiring couriers to move their treasure by sea. Those that could afford the collateral would move treasure for massive payment from the dragons. Those that couldn’t would outfit a ship and steal from those that could.

For a long while, nothing was done about the piracy. The royalty knew that treasure ships were being destroyed, but they assumed it was being done by the Griffins, or possibly other dragons. The idea that their own subjects could be attacking each other was incomprehensible. When Celestia finally discovered the true nature of the attacks, it was too late to do anything about it directly. It was decided that the best course of action would be to send a delegation directly to the dragons to find out why they were moving their hordes and either get them to stop or to change the way they were moving it.

Due to the potential danger and the involvement of dragons, Celestia decided that Twilight and her friends would be best suited for the mission. Since Equestria has no navy to speak of, they would have to charter a ship, and the cheapest place to do that was Trotuga.

Twilight and the girls had prepared for a month’s voyage, packing food, clothing, and other essentials, then removing everything Rarity thought was “necessary” to save space. In the end they had packed it into one cart. One very heavy cart that Applejack had been pulling the entire time.

“Could one of y’all spell me for a bit? Rainbow?”

“Ooh, I really wish I could, Applejack but I’ve got to uh, scout ahead and make sure we aren’t being followed” Dash said before vanishing in a blur.

“Anypony else?” Everypony was suddenly very interested in looking at the road. Everypony except Pinkie Pie.

“I’ll pull the cart Applejack! It’ll be super fun, and you look like you could use a break”

Applejack thought back to the beginning of the trip when Pinkie last tried to pull the cart. Her usual gait of hopping everywhere was less than ideal for pulling the cart. It was more work to run around and catch everything that fell out than it was to pull.

“No, that’s alright Pinkie. Let’s just take a rest by this here pond, it’s almost suppertime anyway.”

The ponies set up around a clear blue pond just a few yards from the road they were traveling and split up to do the necessary chores for a meal on the road. As long as they could manage it, their food would consist of foliage they could find around the road, using the supplies in the cart sparingly. While Applejack rested and the other ponies gathered, Twilight was looking at the map and planning their route. Applejack noticed Twilight’s brow furrowed in concentration.

“How we doin’ on travel time there Twi?” Applejack asked as she found a comfortable rock to lay against.

“Pretty well so far, if we travel until sundown tonight and wake up early, we should arrive at Trotuga around noon tomorrow.”

“That sounds like we’re makin’ great time then. Why’re you frettin’ over the map so much?”

“We are making great time now, but once we reach Trotuga I have no idea what the rest of the Journey is going to look like. We don’t have any good maps of Dragon territory, what we do have is rudimentary at best. If these charts are to be believed, it could take anywhere from 3 to 12 days to get there by boat. We’ll have to rely completely on the captain of the ship we charter.”

“What’s so bad about that?”

“I don’t like having to plan around the trustworthiness of somepony I haven’t even met yet. Especially when they’d have every reason to want our mission to fail. If we can come to an agreement with the Dragons, the livelihood of every pirate there is threatened.”

“Well we knew this was gonna be a tough one going in, but we’ve been through worse,” Applejack yawned. “I’m sure everything’ll ll turn out okay.”

“I hope you’re right Applejack. I’d hate for this mission to be dead in the water before we even start.”

Chapter 2

As Twilight and her friends drew closer to their destination, the road turned from brick to dirt and finally to swampy mud. As the road changed, so too did the weather. Gone were the breezy meadows of Ponyville, the heat and humidity here were a drastic change from their hometown.

Rainbow Dash, who had been convinced to help pull the cart when they got into the wetlands, was the most affected by it.
“Why would anypony ever want to build a town in this horrible place? We may as well be on the surface of the sun.”

“It’s the perfect place for ruffians and criminals to congregate, if you ask me.” Rarity responded. “No civilized pony would ever dream of stepping foot here, and they know it.”

“They may do bad things, but I don’t think you need to speak so harshly about them.” Fluttershy said.

“Fluttershy’s right girls. Whether or not we agree with what these ponies are doing, we’re going to need one of them to help us. You never know who’s listening, so let’s try to keep it civil.” Twilight said. “Get ready everypony, we’re coming up on the city.”

As soon as the words left her mouth, they came across an older stallion sprawled out in the mud. The four of them that weren't tethered to a cart went to his side. Twilight was the first one to speak.

"Oh my gosh, are you alright?"

No response from the old pony.

"Um, Mister..?" Twilight prodded him with her hoof.

"Agh, what's that? who's there?" he muttered as he escaped unconsciousness.

"I'm Twilight and these are my friends. We saw you laying on the side of the road and thought something was wrong. You're not hurt are you?"

"Hurt? Heh heh, no. Nothing a little hair o’ the dog won't fix, anyhow. You're not from around here, are ya? Locals don't pay no mind when yer passed out in the gutters."

"As a matter of fact, we're not," Rarity responded. "We're here on behalf of Princess Celestia, and we need to charter a ship. I don't suppose you'd be willing to help us with that?" She flashed the most manipulative puppy-dog eyes she could muster.

"Well of course I'd be honored to help out on royal business, but you see, I still need that spot of rum. I seem to have spent all my money last night paying taxes-"

"I get it, I get it." Rarity rolled her eyes and floated a bit to him. "Here's your alchohol money, now would you please be ever so kind as to point us in the right direction?"

"Thank you kindly, I certainly would. Down at the end of the main road through town by the pier there's a tavern called 'The Broken Horseshoe.' Great big sign out front, you can't miss it. That's where most of the captains go to drown their sorrows." He nodded and muttered something in farewell before stumbling away.

With those directions in mind, they walked into the town. While passing the first few poorly constructed wooden houses, they assumed that they were just in a less developed area of the town. They soon discovered, however, that the entire town was constructed similarly, the only difference between the buildings was size. Small shacks for living in and larger huts for social gatherings. It made Pinkie wonder,

"If these pirates are supposed to be getting super-duper rich from stealing Dragon treasure, why does their entire town look Applebloom's treehouse?"

"Something tells me the captains aren't keen on investing that money in the betterment of the town." Twilight said while eyeing the multitude of vagrants lying in the streets. "Anyway, I think this is the place we're looking for."

She took a deep breath. "Alright girls, be on guard. There's no telling what could happen in there. These ponies make a living off of fighting and stealing. Stay cool and be ready for anything. They all braced themselves and entered the bar.

Author's Note

This is the official finished version.

Chapter 3

"Well I don't know about you all but I'm pretty disappointed by this seedy pirate bar." Rainbow Dash complained. "I thought there'd be like, knife fights, and dart games, and bottles being thrown at walls. There's just a bunch of dirty ponies passed out at their tables. It's like an old pony's home."

The girls picked a seat at one of the many empty tables in the bar.

"Well, I wouldn't say I'm disappointed," Fluttershy answered. "But it is pretty strange that it's so quiet. Everything I've heard about these places made it sound much scarier than this. How are we supposed to find a captain to help us here?"

"This isn't exactly what we expected, but we can't give up here. Pinkie, you look around and see if you can find somepony who's awake. I'll talk to the bartender and see if he knows anything that can help us."

"You got it Twilight!" Pinkie replied while bouncing away.

Twilight approached the grey bartender pony who was lazily scrubbing glasses and whistling a shanty tune. He cut it short when he saw her approaching.

"Well what a milestone this is. My first customer who didn't come in the door already drunk. What can I get you miss?"

She explained their mission to hire a captain to the bartender. "We were told by one of the locals that we might be able to find somepony here."

The bartender burst into laughter. "Are you kidding? Look around you! The only 'captains' here are the ones that are either too incompetent to rally a crew or too lazy to even try. Take my advice, you'd be much better off going back to Canterlot and admitting failure than you would be throwing your lot in with one of these scoundrels."

"You're telling me there isn't one well qualified captain here?"

"I'm afraid not. Any captain worth their salt is working for the Dragons, and good luck hiring any of them. The way they get paid moving treasure, you'd have to pay your weight in bits to get them to do anything else."

"Is there anypony at all you could point me to? They don't have to be any good, they just have to have a ship that can hold six of us plus cargo.

"If you really must hire someone from here, I suppose I could help you out. I know a captain, not much of a pirate. More of a scavenger really. He sails a Cog, medium sized vessel more suited for cargo than fighting. He follows the raiding parties and loots from them when they get destroyed, then comes back and sells it here. He just got back from his last voyage a couple weeks ago, he's probably looking for another job about now."

"That sounds like it'll work. Where can I find him?"

"That's him right over there." He gestured to the far corner of the bar.

Twilight looked over and saw that Pinkie was talking to the mystery stallion, blocking her view of him. She walked over to see if she was having any luck with him.

“Hey Twilight! You’re just in time, our problems are solved, thanks to Pinkie! This is Captain Monorail.”

Monorail was a brown earth pony with a purple mane and tail. He was a classic pirate, wearing a golden hoop earring in his right ear along with two eyepatches and three peglegs.

“Actually,” he spoke up with a deep gravelly voice that told of a great many nights surrounded by canonfire. “the name’s mono-”

“Yeah I heard, it’s Monorail. Can you captain a ship that can take us to Dragon territory?”

"As I was telling your cotton candy colored friend here, I can. Probably. But the six of you will have to work as me crew. My last crew complained to Pony Resources, something about…” he mumbled something “...harrassment. Anyway. You help run the ship, 500 bits a head, plus 250 for the cart and you got yourself a deal.”

“You expect me to pay over 3000 bits for a blind captain who probably can’t even walk?”

“Well now, you don’t have to hire me. There’s the door.” He said, pointing at the bartender.

“Alright, bye then.”

“Wait wait wait.” Monorail nearly shouted, his voice going up several octaves and losing its gravelly quality. He tried to run after her, falling out of his chair flat onto his face. “Alright you got me, I really need this job to cover the likely upcoming court fees. Please don’t leave. I’ll only charge 1000 bits. No, 500! Please hire me for this. If I had most of my knees I’d be on them right now.”

“Alright, geez, fine. Please stop crying.”

“Oh thank you, thank you so much you won’t regret this.”

The three of them walked, bounced, and hobbled back to the table where the rest of them were waiting.

“Alright girls I’ve found us a captain. This is Monocycle, he’s gonna take us on as his crew for the voyage.”

“Uhh, is nobody gonna bring up that he’s blind and severely crippled?”

“Great observation, Applejack. He is indeed extremely physically handicapped. He also probably molested someone on his previous crew.

“Allegedly molested, and my names mono-” Monocycle coughed.

“Yeah yeah yeah, Monocycle, I heard you the first time. Right, so anyway, this is the best that money could buy here, and I mean that in the worst way possible.” Twilight sighed. “Look everypony, I know this isn’t exactly what we were expecting when we set out, but it’s the only way forward. I’m not willing to go back to Canterlot and say we failed. Not when we had a chance to continue.”

The rest of them nodded in agreement, including Monocycle. “Alright lads,” He said in a pretty terrible pirate accent. “We set sail at dawn.”