Disclaimer: I do not own Once Upon a Time or the characters.


Regina Mills couldn't help the anxious feeling that entered the pit of her stomach. She didn't want to go on this trip. It was her mother's idea after all and for that reason alone there was no way she could refuse. It felt odd, their first family trip without her father.

The smell of sweet salty air drifted in through the cracked windows of the limousine. They were parked, and currently waiting in line for the drop off zone. Only a few exotic and extravagant cars were lined up before them. With a soft purr, the limo started up again and they inched forward in line, just a few feet from their destination on the harbor.

"Honestly Regina I don't know why you're acting like the world is ending" Cora Mills grunted to her daughter as the limousine came to another screeching halt.

Regina sighed quietly, her lips pursed together and dark eyes glancing at the paper lying in her lap for what seemed like the hundredth time that day.

The Jolly Roger, the worn paper read, its text cutting across a large metallic ship that was displayed in the middle to all its glory. Join us for its maiden voyage on April the 2nd. The brunette's fingernail traced alongside the grooves of the ink that was written on the bottom half of the flyer.

A smeared message and signature resided on the underside of the boat. Mrs. Mills, we are deeply saddened to hear of your loss. To ease your mind of the pain you must be feeling please consider joining our family us on our trip to New Orleans. I will give your names to the VIP listing. Register there if you do consider our offer. Sincerely, The Jones.

That was one of the few perks about being a Mills. They were invited to nearly any luxurious event especially if the Jones were involved. Ever since the Jones hit it rich with their cruise lines Reigina's mother had been attempting to set her up with the Jones only heir, their son, Killian.

A sudden yank of the car door to Regina's right snapped her out of her thoughts.

"Miss Mills?" A voice called out before a cap popped over the side of the door. "The time is 4:55pm and I do believe you've arrived to your destination," his voice monotone like that of a global positioning system device.

A small smile peered through her lips as she took her first steps out of the black vehicle.

Her head nodded slightly in his direction. A quick, "Thank you Sydney" whispered from her lips.

The driver leaned over the side of the door and gave her a smile of his own. A soft chuckle burst through his lips, "Just promise me you'll be back in once piece when this whole cruise is over."

"This isn't the Titanic. Then again, I'm not so sure Mr. Glass, I mean it is the Jones' after all," the brunette rolled her eyes and gave a shrug of her shoulders as she walked around the limousine to meet her mother waiting on the other side.

Sydney Glass slipped in behind her, opening the trunk to the car, and began to pack their luggage onto a cart.

Cora propped open her black sun umbrella and watched her daughter with squinted eyes, another grunt crawling from her lips, "I swear you and your father always speaking to the hired help…Learn your class."

The brunette's fingers immediately curled into fists, her heart silently bursting open the gaping hole that had recently begun repair, but there was no sense in arguing. She'd be confounded to a ship with her mother for the entire trip.

"Yes Mother...please...do not speak ill will of Father...his passing still stings" the crippling truth slipped before she could stop.

"Have I taught you nothing? It's best to not have a heart at all. Honestly Regina it's been a month, toughen your heart before I rip it out of you. Speaking of hearts, Killian will be here as well. Perhaps you can finally get to know him and our families can merge as they rightfully should," With a turn of her neck the older brunette was immediately staring at her daughter.

The brunette bit her lip and kept her eyes to the ground. It seemed as if she'd have to wear her mask here too, playing up her class along with her family name.

A smack of the trunk cut their conversation short. The creaking of wheels slipped up behind them. Once more only Sydney's black cap making itself present, bouncing up and down as he spoke behind the tower of suit cases, "I'm going to wheel this up to storage. Have a pleasant and well deserved cruise Mrs and Miss Mills."

And with that Cora Mills took off, embracing herself in the mist of the crowd before the ship. Regina hot on her tails as to not be swallowed by the vast amount of people that were entering.

The two made their way up the ramp that contained the fewest amount of people, making an educated guess that it was contained for the very important people the Jones must have invited.

"Name and age?" the voice was soft and higher pitched like that of a child.

Regina slightly leaned to the side and glanced around her mother to catch a glimpse of who was citing their registration.

Standing at the end of the ramp, before the Mills, was a blonde woman dressed in a white tank top, navy blue skinny jeans and a pair of dark brown boots. Two scuffed up sneakers wrapped around her golden mane, connected to a small brown haired boy draped across her neck and shoulders.

The body of the boy bounced as the woman holding him readjusted her feet, "Hey what did you forget to say kid?"

"Oh! Name and age please" the child restated, clipboard gently tapped the back of her head as he leaned forward a bit.

Cora scoffed, rolling her eyes at the pair before her. The black umbrella that she had been carrying above her head was now withdrawn and collapsed her side as she spoke, "Cora Mills, twenty six years of age."

The blonde once again shifted her weight, gripping onto the ankles of the boy as he leaned over her golden tresses, his eyes roaming over the woman.

"Mom it says that she's fift-" the brown haired boy began but was cut off short when the woman shifted him up.

"Nope! Not a day over twenty six Henry" the blonde shot a forced smile at the woman dressed in black before her. She quickly dug into her pocket and pulled out a small key with a metal dog tag on it.

"How adorable," Cora rolled her eyes and drew her umbrella. She quickly yanked the key from the blonde's grasp and pushed the two to the side as she made her way on board the Jolly Roger.

Henry fidgeted again on his mothers shoulders, "Can I go play with the other kids now?"

The blonde gave a quick sigh and plucked the child from her shoulders. With a quick exchange of the clipboard, a pat on the head, and a quick reminder to be safe and to play nice, she sent him off.

"You are going to ask me the same aren't you?" Regina questioned drawing the green eyes of the woman before her.

"Yes..Sorry about that. Kid's gotta learn his manners" the blonde began as she ran her free hand through her hair. "Right so, name and age please."

"Regina Mills, twenty five, miss..?" the brunette questioned back.

"Mills…M-I-L-L-S," the blonde scanned on the clipboard, tossing a set of keys at Regina her green eyes glanced back up. "Emma Swan, Ma'am"

Out of the corner of her dark eye she saw her mother watching.

"It appears your son does a better job than you do. Or at least has a higher brain capacity for how to spell" the brunette's eyebrow rose in amusement of each letter that fell from the blonde's lips.

Emma rolled her eyes in annoyance handing Regina a small map of the deck plans, "Make a left and head down past the crow's nest and you'll hit double doors. There will be an elevator to your right, and stairs to your left. Take them and head to any deck you want."

Regina eyed the key's dog tag, "I'm here with my mother."

A small smirk appeared on the corner of Emma's lips. "Apparently they think you're responsible enough to leave dear old mom behind."

The brunette's brow rose once more this time in a bit of shock.

Their challenging glaze cut short when a group of four children raced between the women chasing a soccer ball, Henry leading the pack.

"Hm..I wish I could say the same about your son," a bright smile appeared on Regina's ruby red lips.

The blonde sighed and handed the clipboard to a passerby and then darted after her son, "Henry I swear if you get us kicked off!"

With a smirk the brunette took her first step onto the Jolly Roger.

"Finally now that you're done wasting time with the peasants," Cora said gently tapping Regina on the calf with her umbrella tip, "Let's find our rooms."

Regina glanced around the ship once more, a bundle of blonde hair catching her attention.

Emma came rushing back the way she left. This time dribbling a soccer ball between her feet, Henry now slinging off her shoulder as she carried him one handed. Three other children followed bursting with laughter as they chased the woman on the deck.

"Ugh I will never understand why the Jones agreed to let children on this cruise ship" Cora grumbled following her daughter's gaze, "Children and unprofessional peasants."

The brunette nodded at her mother slightly before leading them in the direction that Emma had given her. The two women made their way through the double doors, immediately hit with the smell of warm apple pie.

"Dining deck," Regina said glancing down at the map before checking her key tags. "Suite 108 for me and what of you Mother?"

The older brunette checked her tags as she called for the elevator, "107."

The elevator opened with a pop and the two women stepped in, ascended as they chose the top deck. Neither of them spoke during the short trip upward.

Once they arrived they traveled down the hallway until they reached their rooms. Doors to both rooms were hanging wide open, a small cart just emerging from the doorframe. The luggage attendant nodded toward the two and began his way to another room along the same hall.

Upon entrance into her room Regina couldn't suppress the smallest grin. It was truly beautiful and fit for a queen. A large, white, king sized bed decorated with rose petals greeted her, with a small note standing on the middle pillow. To her right was a fairly large dresser and beside that were her bags of luggage. Behind the bed was a row of windows gleaming with the view of the ocean. A small sliding glass door was in the far corner of her room, next to her private bathroom.

"So the rooms come with a nice little balcony and a small mini bar" Cora said as she stepped into her daughter's room, umbrella tapping on the cabinets of the dresser. A wicked grin pierced her thin lips, "Rose petals..it appears as if you have a suitor."

The grin on Regina's lips was wiped clean immediately knowing the hidden meaning behind her mother's words.

With a rattle and a loud creaking sound the ship pushed from the dock and began to move. Both woman staring out the window as the crowds of people began to shrink in size as they headed onto their journey into the ocean.

"I'm assuming you want to go say hello to the Jones, Mother. Allow me to unpack and I'm sure to meet you all in the dining hall" the younger brunette began as she crouched down and unzipped her largest bag.

"Of course," Cora replied as she slowly made her leave, pulling her daughter's door shut.

Regina ran a hand through her short hair and walked up to the glass sliding door, watching the waves crash against one another for a few minutes before taking a closer examination of the note on her pillow.

I hope you find your room to be accommodating – Killian. Her dark eyes rolled in annoyance and tore the note in two. She tossed it into the small trashcan in the corner of her room before getting back to unpacking her clothes.

With a quick change into a short black dress she left her room and descended the elevator. Her black stiletto just barely made it out of the elevator before someone nearly tripped on it.

"Ah sorry!" the bundle of blonde hair apologized darting off into the dining hall.

Regina's eyebrows bunched in anger. Gripping onto both sides of the elevator and she thrust her head out to get a glimpse of the familiar blonde, a grumble rising from her lips, "Swan."

Following the blonde's path the brunette walked through diners, dives, and restaurants. No doors enclosing the dining areas until she reached another set of double doors. A small bit of surprise danced in her eyes as she was greeted with the hostess.

"Oh, uh Ms. Mills," Emma began readjusting her red tie.

She smirked at the woman before her, "Late for your shift Miss Swan?"

"You could say that. A friend of mine called out so here I am," an unexpected laugh bubbled through the blonde's lips.

"Should I assume you'll be dining with your mother?" Emma spoke up as she scanned the table listings before her.

"And your son is?" the brunette questioned.

Emma faltered for a second, her gaze zoning in on the dark eyes before her, "He's on deck eight, children's section until I get out."

Regina nodded toward the hostess, resting her hand upon her hip, waiting for the blonde to show the way. "I must say the waitress look is a step up from your civilian clothes," she teased, hand gesturing to the white button up blouse and fitted black slacks, as the two headed down rows of tables.

The dining room was composed of glass windows so the diners could examine the night. Two magnificent chandlers hung on the high ceilings, gently dangling to and fro with the force of each wave knocking into the ship.

Emma stepped to the slide and bowed slightly, extending her hand to the group of people seated at the small round table.

"Regina Mills," Leliana Jones gushed from her seat next to Cora, "Why I haven't seen you since you were a child."

The brunette took the seat next to her mother and smiled politely at the older woman.

The blonde before the table cleared her throat, gaining everyone's attention before reciting her normal waitress routine. "Thank you for joining us for our early dinner service. I will get your server immediately but before you begin is there anything you'd wish to drink?"

"Make mine a Captain and Coke" A dark haired man with stubble announced as he took a seat at the table, winking at Emma then at Regina.

Mother Jones giggled softly before bringing her hand up to fix her son's head of hair, "How clever you are. I'll take red wine, the same for my guest here" she motioned to Cora.

"And you Ms. Mills?" Emma nodded turning her direction to the youngest at the table.

"Apple cider if you have it" Regina announced as she placed a napkin on her lap.

Once more Emma nodded, her blonde curls bouncing in contrast against her white blouse, and with that she headed off to find their waiter.

Cora gently prodded her elbow into her daughter's side, a wide grin on her face as Leliana spewed meaningless conversation in her direction.

With an inward and silent groan Regina made eye contact with Killian. The man made his best grin, eye again winking in her direction.

"So Captain Killian Jones hm?" the brunette asked.

His grin got wider if possible as he replied, "Well it seems that I am love. What have you been up to with your dear old dad's business?"

Silently shooting the waiter a look of thanks when he delivered their drinks, she took a sip of her cider.

She kept her face straight, never faltering under his gaze, "It's not the same without him, but we are managing."

"That's good then," Killian reached for his drink taking a sip before the waiter asked for their orders.

Leliana Jones ordered for the group, a famous seafood feast filled with grilled fish and eloquently cooked lobster.

Halfway through the meal the conversation became few and far between for the youngest at the table.

Gazing at the windows Regina suddenly spoke, "Excuse me. I'd like to get a bit of fresh air."

The brunette made her way to the giant wall of windows. Her head tilted back slightly to examine the stars in the sky. An attendant standing near her quietly asked if she would like to go out on the deck.

She tilted her head and nodded slightly. Just a few steps away he turned a handle and opened a glass door, the salty breeze instantly hitting her nostrils.

With a polite smile she slipped outside, a motion detecting light turning on and shining above her head, as she walked over to the golden railing. Her fingers danced along its cold surface before gently grasping it in her hands, as she continued to gaze at the night time wonders.

"Oh..I thought I'd be out here alone" a voice called from behind her, gently shutting the door as they stepped out onto the bare deck.

Regina swiftly turned her head and peered through the light until the person came up beside her.

"Miss Swan I'm beginning to think you have a slight stalking problem," the brunette stated before turning back and looking at the stars.

"Hey if you want to play that game I was on the ship first," the blonde laughed softly, unwrapping two cookies from her palm, "Or maybe you're just picking my favorite spots on the ship."

For the first time that day Regina quietly laughed. The weight of the situation in the dining room seemed to lift from her back and into the pitch black night.

A sudden breeze past through the air, coating and freezing Regina to the bone.

The silent shiver did not go unnoticed and the blonde quickly unzipped her leather jacket, handing it to the other woman.

"You really expect me to wear leather?" Regina questioned her eyebrows down as she examined the red piece of clothing. She gently flicked it with her finger acting as if it was covered with disease.

Emma shrugged, pulling it back to her side, bringing a chocolate chip cooking to her lips to nibble.

"Why are you out here?" Regina questioned.

With another shrug the blonde replied, "Probably the same as you. Just needed some air and some time to myself."

A few more moments passed and another breeze came barreling through. This time instead of offering Emma opened the jacket and rested it softly on the brunette's shoulders.

Regina pulled it closely to her body; a soft whisper of a thank you was lost in the wind.

"So the Captain huh?" the green eyed woman curled her arms over her chest and rocked on her heals. "You Mills must be pretty big shots."

"Already asking personal information are we?" The brunette teased her eyes bouncing from star to star.

Emma raised her hand and dismissed the comment. Her blonde locks bouncing as she began walking a few more feet down the deck, with each step another motor sensor light turning on above her.

"Emma just a couple more minutes before they're gonna be looking for you," another blonde head of hair poked out of the glass door and called to the Swan girl.

She shot the girl a thumbs up and pulled a cell phone out of her slacks, the door closing with a click.

"Ah crap" Emma mumbled quietly, marching up to the door, "Henry why do you always fall asleep during story time?"

"My father passed recently. And my mother thought it would be a great idea to set me up with someone just as rich" the words flowed from the brunette's lips.

The sound of the blonde's boots clicking against the deck suddenly stopped.

"The Jones' own a cruise line and we own a travel agency," the shorter woman began before recalling her father's famous slogan, "Magical Portals, we take you where you want to go."

Emma came up next to her and hesitantly placed a hand on the stranger's lower back, her green eyes meeting brown. The actions were more than words itself. She didn't have to say that she was deeply sorry for the loss that the Mills family experienced. She simply expressed it.

"Whatever you're looking for here...whether it be love or just time to grieve I'm sure you'll find it. Everyone finds their happy ending. At least that's what Henry preaches about," the blonde said softly, a blue haze emerging from her lips as she spoke, before showing Regina a simple smile.

The brunette only stared back at the green eyes next to her. Tan fingers gripped the leather jacket and handed it back to the hostess. Her lips pursed, no voice coming out any time soon.

Emma accepted her jacket and took a few steps away before turning back. Her hand outstretched with her last chocolate chip cookie in between her fingers, not moving until the treat was taken.

"Whenever Henry is feeling down, or gets hurt I give him something sweet just to sooth the pain," she softly announced.

"You need to stop giving your child so many sweets or you'll send him to fat camp or through sugar shock" the brunette teased unable to help her smug grin.

The hostess smiled at the teasing comment, gripped the glass door handle and entered the dining room.

Quietly gazing at the moon over head Regina nibbled on her cookie. Once the cold began to penetrate her skin once more she headed back inside. Her stomach fully satisfied after the delicious sweet.

"We were just about to send Killian to get you. So how are you fairing the sea dear?" Mrs. Jones asked glancing up from her lobster before dipping a piece of its tail into a dish of butter.

Regina flashed the older woman a charming smile, "I think I'm beginning to take a liking to it. Thank you."

"Well they do say after the first night you either get sick or you get your sea legs" Killian interjected chugging the last of his beverage.

"Hm..well this is her first cruise so I wouldn't be surprised if she does fall ill. Perhaps you can give her a hand with those sea legs" Cora spoke up, her knife sharply cutting through a salmon steak.

The younger brunette bit her lip, glancing at the clock, seeing that it was now nine at night. She inhaled deeply and smiled innocently at Mother Jones as the older woman laughed.

"I actually am feeling a bit under the weather. The trip from Storybrooke to here was a very bumping ride in the back woods" Regina replied nodding her thanks to the Jones before standing up and taking her leave.

The Jones said their goodbyes with Cora giving her daughter a small wave, "Do head to bed dear. We don't want you sick for long."

The second she exited the double doors and pressed the button to the elevator a wave of relief hit her. One day over with the Jones and one day done with her mother. She just needed to head to bed and prepare for tomorrow's battle.

When the elevator opened she again found herself in the company of the blonde haired woman and the brown haired boy from before. His body finding what seemed to be his favorite spot draped over his mother's shoulder.

Emma made a quick notion to her lips to keep quiet as Henry softly snored against her neck.

Regina nodded slightly and went to select her floor, brows furrowing together finding that it was already selected. She sighed inwardly. It seems as if she would be seeing a lot of Miss Emma Swan during this cruise.


AN: Hey guys, sorry it was a short chapter but I wanted to get a feel on how well you guys enjoyed the story. Based on how well Set Sail does will probably end up deciding how many chapters this story gets. Don't forget to review if you think it deserves it.