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Episode 165 Once Upon a Zepplin Aired:
October 7 2017
We find Twilight inside her castle hard at work but bored to tears as her workload is nowhere near done. Worse still, she breaks her quill, leaving her to get one from Spike's stash of quills. However, a letter breaks their concentration. It entails a cruise by zepplin airship with her entire family but it's not an option to Twilight with her workload piled high. Spike notes Celestia's regularly scheduled vacations, even with her duties but when that doesn't convince her, he physically shoves her toward the door as extra incentive.
Spike even agrees to tackle the paperwork and eventually Twilight gives in but Spike is already aware of Twilight's habit of schedules and correctly predicts her using one for the trip. Some time later, Twilight and her parents are among others boarding the zepplin airship as the trio discuss the matter of a "relaxing vacation". Feet away, Shining Armor is eager to board, assuring his air sickness has long since passed but they all get an earful welcome from the captain. With everyone on board, the ship departs (and reveals its awful design in full).
Once inside their lobby of sorts, Twilight learns that their so-called prize seemed rather ambiguous (and that should've been a red flag to all of them, including YOU Twilight). Sure enough, Twilight's mom assures that signing paperwork and not asking questions is the way to go. As for what to do, Twilight shows her schedule of activities taken from the zepplin itself and organized by interest. The schedule also manages to work out perfectly for Twilight's activity, seeing the Northern Stars, which is right along their flight path.
The only problem is they don't have anything to do at the moment but the captain chimes in with an idea of his own that the group are willing to take part in. Back on deck, while Shining Armor attends to Baby Flurry Heart down below, the captain begins his tour, leaving Twilight to wonder how they know about Cloudsdale and the Weather Factory it contains. As the tour progresses, ponies are finding themselves more and more interested in Twilight and her family. The group move to the other side but the captain is quick to point out another landmark and this time some incorrect info.
Her mom and dad appreciate the tree anyway but Twilight continues to get bombarded with excited passengers. They pass over the Crystal Empire where the captain makes a complete nonsensical statement (perhaps running out of convincing things to say but most of the crowd eats it up anyway and it's not like I'd know all the info either). However, none of that compares to what Twilight and Cadence see next, as the passengers cross the line to being obsessed over Twilight with mock horns, wings and t-shirts.  It's enough for Twilight to try and put an end to it and asks where the captain is.
Luckily, passengers point the way and she finds it's Iron Will that's behind all this, having changed careers after his previous failure. Unfortunately, the cruise is all about the princesses of Equestria, leaving Twilight fearful. They meet in the lobby of the airship where Iron Will notes the fine print that was clearly not read. Should Twilight not want the cruise, Iron Will will cancel it and leave everyone on board disapointed. As a compromise, Twilight proposes a deal to Iron Will whereby she'll take part in activities requested by the passengers while her family goes off and does what they want.
Iron Will accepts and escorts Twilight to the top of the Deck where a prize is to be awarded. The award goes to Star Tracker, whom is rather nervous to accept it but Iron Will notes that Star Tracker will spend the day with Twilight and her family as an honorary member of the family. Now it's time for Bingo and Twilight is in charge of calling out the numbers. Later, Shining Armor is taking part in the tiny boat race despite still being air sick but he tries to assure he's fine. Twilight is about to put a lifejacket on Shining Armor but is put on being the race official, leaving Iron Will to do that and her mom joins in the race.
While Twilight's mom enjoys the one-sided race, Shining Armor never took part so her joy fades away. However, once Shining Armor is out of the water and being escorted back inside, Iron Will notes that it's race 1 out of 10, leaving Twilight to attend to the additional races. She finishes up in time to see Princess Cadence with Baby Flurry Heart at Peewee Playtime and learns the good news there. There's still more for Twilight to do and she hopes she doesn't miss her mom's barrel ride attempt or the Northern Stars that night.
Unfortunately, Star Tracker reminds her of her duties and off she goes.  Furthermore, Cadence takes Baby Flurry Heart away for her nap. Twilight finishes up and races to catch her mom at Neighagra Falls for the barrel ride, only to find that she's already too late. Her mom sees her disappointment and suggests taking a break from the activities but Twilight plays it off and gets them to accept her ways. Iron Will gives Twilight one last job and lets everyone know they have a final chance to get an autograph from Twilight.
By the time she's just about done, the Northern Stars have begun and her parents are already taking in the moment. It brings her to tears, then anger as she takes it out on Star Tracker, whom ends up with an injured hoof as a result. Twilight storms off, leaving Cadence concerned enough to comfort her. In fact, Cadence reminds Twilight that she'll always have duties as a princess and Twilight heads off to not only set boundaries but apologize to Star Tracker, whom is under the care of the others in the family. When Twilight emerges, Star Tracker panics and wants to leave but obeys Twilight's order to stay.
Twilight apologizes to him and shares her realizations. Once she gives her idea of what to do off-schedule, the others are in shock but it's something they can all enjoy, even honorary members of the family like Star Tracker. They're taken on Deck where ice cream is being served. Star Tracker agrees to also back off but Iron Will does not as he brings their attention to the ice cream cart. Star Tracker doesn't approve and has to face Iron Will's angry eyes. Luckily, Twilight sticks up for him and takes the headset away from Iron Will to provide a speech of sorts to share her feelings and true intent for taking the cruise.
The passengers then wonder why it was advertised as a cruise about the princesses when clearly that's not what the cruise was supposed to be about. Iron Will makes the stipulations clear before jumping ship and using a parachute part-way down. Later that night, Twilgiht has her own idea for what to do next but is treated to a family version of the Northern Stars. The event touches Twilight's heart but she's surprised Shining Armor is participating despite being air sick. Shining Armor promptly gets down and everyone hugs as Twilight has confirmed that family is the only thing she ever needed.