"Good news, men!" Killian announces, jumping aboard his ship the next morning. "We found ourselves amid a war in this land, a grand Civil War, and I found us a way to use our resources to help out those in need. As you are all abundantly aware, Captain Hook does night back down from a fight against tyranny!" He pumps his hook in the air, and the crew cheers. "But I, of course, will give you all the option to stay aboard the Roger, because what we are about to embark in is extremely dangerous, and if you choose not to stay with us, I'll give you what you need to stay here in Baltimore, but you must leave now."
He gives the crew a few moments to make up their minds, but is pleasantly surprised when every single one of them stays on the deck of the ship. It's a proud moment for him as a captain, and he flashes them a smile to show them. He then looks around, sees all the men on the docks around them, and leads his crew into their below-deck quarters.
"Aye, boys, then this is what's going to go down. The Jolly Roger has been commissioned to be a secret slave runner for the United States. These men are fighting and dying in a war that started because tyrants wouldn't acknowledge them as people, so we are going to save them. We will be leaving midday tomorrow to make port down south under the cover of darkness. That gives our friend enough time to get word down there and have everyone organized by the time we make port. So, for tonight, we are all staying on the ship, no questions asked. I'll make sure everyone is fed well as the day goes on; the tavern is not far from here, and they fully support what we are doing. But - I cannot be more serious about this matter, boys - you cannot speak of this to anyone outside of the Green Dragon." He dismisses them, giving them the day to themselves to spend in the town, doing whatever their hearts desire.
Once the crew clears off the ship, only the three of them remain: Killian, Emma, and August. Killian busies himself around the ship, doing all he can on his own to prepare them for their journey, obviously filled with adrenaline. This, however, leaves Emma and August alone in the crew quarters, able to pick up their conversation where it was left in the dust of the tavern.
But as soon as August opens his mouth to speak, Emma is already halfway up the steps to the deck, locking herself away in Killian's cabin, just as August locked himself in his.
She lays down on the hard bunk, unable to stop herself from thinking over all that has happened, just in the past day: finding themselves amidst a battle - a war - meeting someone so much like her pirate that Killian then offers his help to them, sacrificing his ship, his men, his life to this cause he has just learned of - a sacrifice she is not sure she is ready to make.
She dozes off, lost in her mind, rocked to sleep by the rough waters churning in the harbor. Her dreams are full of storms, cannons, gunfire, tyranny, and death, not a solid, story-like dream, but instead a collection of snippets. When she finally awakes, she finds Killian sitting at the foot of the bed, keeping watch over her; then notices the darkness of the room, which she quickly fills by lighting the candles with her magic, not giving it a second thought. At first, she wonders how she seems to have slept all day; then she sees the flash of lightning outside the window, hears the crash of the thunder and the roar of the wind, and realizes that it is not nighttime, simply storming.
It takes her a few moments to fully awake before she realizes what she has just done, which Killian noticed right away: conjured fire. Used her magic, here, in the Land Without Magic. She looks up at him, still sitting at the foot of the bed, his eyes now the same stormy grey she sees through the window, and together, they come up with a plan.
The storm has not faltered by the time they set sail the next day, a storm more violent than Emma ever remembers home in Misthaven. But unlike the other storms Killian has had to sail through, he now possesses his secret weapon aboard the Roger, which gives him a new shot of confidence: the magic-wielding princess, able to calm the seas around them while the rest of the ocean rages, keeping them safe, a trick Killian insisted Emma practice the night before. He has always seemed to have luck on his side, but he never imagined that his luck would come in the form of Emma Swan. He can't help but watch her as she concentrates, her silver-blonde hair billowing around her from the winds beyond her control.
She has bewitched him, drawn him out from under the hard shell of Captain Hook that he created for himself, something that he had feared from the moment he began creating it; but with her, none of it mattered. For her, he could let down his guard and not be afraid of what would happen to him.
Their first journey is by far the rockiest: Killian is unsure of exactly where to make port, though the storm has ceased, until he sees a group of torches on the shore. Once all the men are aboard, ten of them total, he steers the ship in the other direction, and has just gotten the wind to take to the sails when he notices a ship behind them, just out of the reach of the cannons. Though he knows she is exhausted, she is his only choice, and she uses the rest of her energy to summon a storm above their unwanted guest, creating a wall of water so thick they cannot see far from the edge of the ship, losing their course and running ashore. She continues the storm, though, until they are on the horizon, completely unable to follow; then she gives Killian the clear to release the sails and make way up the coast to their destination, a small coastal town further north than Baltimore called Dover.
A friend of Floyd's is on the dock to meet them, matching the description given to him down to the color of his shirt, and while this man insists that the Roger will be safe and sound in the harbor, Killian refuses to leave the ship. Up at the very break of dawn the next morning, they are off again to rendezvous in Baltimore with Floyd before sailing farther south again.
They do this four more times scot-free, thankfully avoiding any storms like the one on their first day, bringing nearly fifty previously-enslaved men, women, and children - and four dogs - to safety in different northern towns.
It is the sixth time that they arrive in the Chesapeake Bay area beyond Charleston when something is very wrong: instead of the hustle and bustle of a regular day in the port town, the sky is filled with the flashes and deafening booms of a battle, happening just beyond the limits of the town. .
Killian sounds his battle cry as soon as they are docked:
"I would never force a man to fight a battle that is not his, for it is simply not good form. I, however, am not privy to running from fights when a man's freedom is on the line. I have always allowed you all to choose your own fates aboard this vessel, and I will do the same thing today. I will choose to go to battle here, but you are each free to choose for yourselves, knowing no judgement will come from me, nor any man on my crew!"
With this, he flashes a smile and a sly wink at Emma, standing at the helm, and jumps down off the ship onto the dock, heading straight towards the battle - and every single man aboard the Jolly Roger follows suit, with August bringing up the rear, after silently looking back to Emma, sadness in his pale blue eyes.