That evening, Twilight stood with her forehooves hooked over the rear railing of the main deck, looking up at the stars overhead, and downward at the clouds passing below.
She sighed unhappily.
Then she heard her friends approaching, chatting excitedly amongst themselves.
Spotting Twilight, Rainbow swooped over. "Hey, Twilight! Great first few days, huh? We launched the school without anypony stopping us. We got all of Equestria's allies to send their students here. And the students really like me! I'm not just Professor Egghead to them! Hah! This is awesome! We're a real pirate school now, huh?"
"More precisely," Twilight replied, "we're an extra-territorial, extra-legal, unaccredited, international educational facility."
"Eee-yeah," Rainbow replied. "So, like I said... pirate school!"
Pinkie popped up beside Twilight wearing a pirate's hat and eyepatch. "Arrr! Shiver me test plans and gimme a number two pencil, matey!" Then she giggled. "I've never had so much fun! And the students love my classes!"
"I really like how the students themselves are getting along so well," Fluttershy said. "They're all so excited to be here, we're not having any problems."
"Absolutely, dahling," Rarity said. "We just need to be sure to keep them busy, and having fun learning. Idle hooves, you know."
"It's definitely workin' all raight so far," Applejack agreed. "Better than we could'a hoped!" Then she looked concernedly at Twilight. "So why the long face, sugarcube?"
Twilight sighed again. "I'm sorry to be so gloomy. You're all doing your very best, and I couldn't wish for better. I just wish... I wish we didn't have to operate the School outside the rules, outside the EEA's guidelines. The guidelines themselves aren't wrong. In coming up with rules and procedures for the School, I pretty much reinvented a lot of what they consider standard practice. It's just the EEA's approach that's wrong... their resistance to sharing what we know of Friendship with other cultures."
"I hear ya, Twi. And it's a darn shame things have to be this way. But even so, we're doin' a great job."
"Exactly!" Twilight gestured around at the Friendship School itself. "I look at the progress we've made so far, just in getting the School up and running, and I can tell that we're doing something that's right, something that's necessary... so why does it have to feel so wrong?"
"It's not easy," Rarity agreed. "It never is when you're a trend-setter. You just have to grit your teeth and do what's needful. Show the critics what they've been missing, help them see what they haven't seen up to now."
Spike reached up to touch Twilight's shoulder. "We're all with you, Twi! We all want to make it work as much as you do."
"Thanks, Spike! And thanks to all the rest of you as well."
She paused, and looked up at the stars again. "I wish Princess Celestia could see this place, see what we're doing here. Not being able to talk with her about it, not being able to share our accomplishments with her, that's hurt more than anything else."
"I know she'd be proud of ya, hon," Applejack said. "Don't ever think otherwise"
Twilight nodded. And then she drew herself up, her face set determinedly.
"We're going to make this work, everypony!" she said. "And when we get back to Ponyville, we'll have something to show the Princesses -- to show to all of them. Something that proves that what we're doing is right!"
"Now you're talking, Twi!" Spike said, pumping a claw.
"That's the spirit, dahling!" Rarity said.
"Yeah!" Rainbow punched the air with a hoof. "No guts, no glory!"
"All for one, an' one for all!" Applejack shouted.
"And a cupcake in every hoof!" Pinkie cried, giggling.
"Yay!" whispered Fluttershy.
The seven of them grabbed each other in a crushing group-hug, laughing uncontrollably...
... and completely unaware that they were being observed.
In the gloom of the foredeck, beside the helm wheel, Tempest Shadow stood watching them, silent and unseen.
Grubber was standing next to her, messily devouring a cupcake.
"Look at them," Tempest finally said. "So happy all the time, no matter what troubles they're facing." She snorted. "I'm a pony too, and I'm still getting used to it."
"Yeah," Grubber said. "Kinda nice though, while it lasts. And hey, great job, boss... gettin' Twilight to put you in charge of everything. Just like the Storm King all over again, huh?"
"It wasn't all that hard." She glanced at him. "The head of state always wants someone to manage all the troublesome little details. Speaking of which, did you get that kitchen supply list from Pinkie?"
"Sure did," Grubber replied. "Bright and early tomorrow, I'll grab one of the skiffs and go shopping. Heh, heh! Kinda nice bein' on an expense account again!"
"Don't get carried away." Tempest glanced at Twilight and her friends, then leaned closer and lowered her voice. "And while you're at it, you can make a side-trip. I'll want you to take a message to our friends... tell them to be ready in a couple days, to lend a claw..."
"Seriously, boss?" Grubber's eyes went wide. "We're gonna do it? Ohhh, yeah! I can't wait to see the looks on their faces!"
"Keep it to yourself for now... loose lips, you know."
"Gotcha, boss!" Grubber finished the cupcake in one gulp, and then grinned nastily, rubbing his paws in anticipation.
Tempest smiled as well, looking across the Friendship's deck at Twilight and her friends. They were so trusting, so unsuspecting. Such easy targets for those who might wish them harm. Tempest knew a thing or two about that.
She thought back to the curious message-scroll that Grubber had brought to her room in Twilight's castle, shortly before they'd all left to board the Friendship:
To Commander Tempest Shadow:
It has come to the attention of certain highly-placed and influential authorities that the Princess Twilight Sparkle has been engaged in an ill-advised venture, which is both highly unorthodox and illegal. This venture will likely take the Princess outside of the relative safety of Canterlot and Ponyville for substantial periods of time. And it has also come to their attention that you, as the Princess's nominal bodyguard, are in a unique position to see to both the Princess's safety and security, as well as to the overall success of this venture.
Should anything happen that might threaten the Princess's safety, and expose the illegality of this venture and her lack of judgement in organizing and supporting it, these authorities would like to assure you that an appropriate response would be made. And that the Royal Guard always has a place for those who are loyal to Equestria, and respectful of its well-considered, approved guidelines for the operation of its educational facilities.
Sincerely,
A Mutual Patriot
Tempest had read the letter twice, just to be sure she hadn't missed anything. And then she'd laughed delightedly. And burned it to avoid incriminating evidence.
She grinned, looking at Twilight and her friends.
The letter had given her an idea. And now that all the international students were aboard, she could finally move forward with it. She had a surprise in store for all of them, a real wake-up call.
Tempest loved surprises.
They always worked in her favor...