Chapter 2
CHAPTER 2
T he interior of Margarita Max's was exactly what Tess had imagined. The wooden beams were draped with string lights, their dim glow mingling with the neon signs advertising every tropical drink known to man. The bar itself stretched across one side of the room, covered in scuffs and dents that told stories of decades of spilled cocktails and overenthusiastic patrons.
Leah's first thought, however, wasn't about the charm of the place but about how sticky the floors were. Her sandals clung to the surface with each step, and she couldn't decide if the sensation was more unsettling or just depressing. The air inside was thick with the competing scents of lime, stale beer, and whatever tropical-scented cleaner they used to mop the floors, presumably between spring break seasons.
"This place has character," Tess said, beaming as she spun slowly to take it all in. Her enthusiasm seemed to brighten even the darkest corners of the bar, where ancient fishing nets and plastic lobsters created shadows on the walls.
"It has something," Leah muttered, glancing toward the bar where a middle-aged woman with a no-nonsense ponytail was wiping down glasses with the efficiency of someone who'd done it a million times. Her nametag read "Connie," though the letters were faded as if they'd been through as many Key West summers as the bar itself.
The walls were a testament to decades of island life, covered in photos of fishing tournaments, hurricane parties, and tourists who'd probably long since forgotten their nights at Margarita Max's. A dusty paddleboard hung from the ceiling, its surface decorated with the bar's logo, a cartoon parrot wearing sunglasses and holding a cocktail glass in its wing.
"Excuse me," Tess said, her tone chipper as she approached the bar. "We heard you're hiring?"
Connie looked up, her sharp blue eyes scanning the sisters with the precision of a drill sergeant sizing up new recruits. The towel in her hands never stopped moving, as if cleaning glasses was as natural as breathing. "You ever worked in a bar before?"
"Well, no," Leah started, but Tess cut her off with a confident laugh. The kind of laugh that had preceded many of their more questionable business ventures.
"Not professionally," Tess said. "But we've spent plenty of time on the other side of the bar, and I'd say that makes us pretty qualified. Plus, we're quick learners." She gestured to the row of bottles behind the counter. "I bet I could name every type of rum you've got back there."
Leah resisted the urge to groan. Tess's charm had gotten them into plenty of situations, but she wasn't convinced it would get them out of this one. Still, she had to admit her sister's ability to turn every situation into an opportunity was almost impressive. Even if that opportunity involved sticky floors and drunk tourists.
Connie arched an eyebrow, setting down the glass she'd been polishing with a soft clink. "You good with drunk tourists? Broken glasses? Karaoke?" Her voice suggested these were merely the tip of a very large, very sticky iceberg.
"Absolutely," Tess said without missing a beat. She leaned against the bar with the confidence of someone who'd never had to clean one. "And Leah here is great with numbers. She'd make an excellent cashier. She used to manage million-dollar accounts in Boston."
Leah gave a tight smile, wondering how her MBA had led her to this moment. "I'm also good at cleaning sticky floors." She demonstrated by lifting her sandal with an audible peeling sound.
Connie's lips twitched, almost a smile. A Jimmy Buffett song played softly in the background, as if providing the soundtrack to their descent into island unemployment.
"Fair enough. You're hired. Part-time for now. Show up tomorrow night at six, dressed in black. Comfortable shoes. And don't show up hungover."
"That's it?" Leah asked, blinking in surprise. In Boston, hiring processes had involved multiple interviews, background checks, and at least one personality assessment.
"This is Margarita Max's," Connie said, returning to her glass polishing. "The bar's low. No pun intended." She handed each of them a napkin with scrawled instructions, her handwriting as efficient as her movements. "Be on time. And remember, tomorrow is Trivia Tuesday. It’ll be crazy in here."
As they stepped back into the blinding Key West sunshine, Tess clapped her hands together, the napkin fluttering in her grip. "See? That was easy. And we didn't even have to beg. Although I was prepared to if necessary. I had a whole speech planned about our extensive experience in customer service."
Leah shielded her eyes with one hand, staring at the napkin in the other. The instructions were simple: wear black, bring a positive attitude, don't be late. Nothing about the complex drink recipes she'd need to learn or how to handle rowdy bachelor parties. "I can't decide if this is a good thing or a sign that we've hit rock bottom. Did you happen to notice that we have no idea how much we’re going to get paid for this adventure?"
"It's not rock bottom," Tess said, looping her arm through Leah's as they navigated the crowded sidewalk. A group of tourists on rented bikes swerved around them, their helmet straps flapping in the breeze. "And I assume it’s more about the tips than anything else. Look at it as a stepping stone. We'll be slinging margaritas and charming tourists in no time. Think of the interesting people we’ll meet."
Leah raised an eyebrow. "Interesting how? Like someone who owns a yacht and needs a crew? Or someone who leaves a $500 tip because they accidentally paid with the wrong card?"
"Either works," Tess said with a grin. "Though I was thinking more along the lines of a mysterious stranger with a business proposition. Or maybe a wealthy widow looking to invest in local talent."
"Your definition of 'local talent' concerns me," Leah said, but she was smiling. Something about Tess's relentless optimism was infectious, even in the face of their current situation.
They walked in silence for a moment, the heat of the sidewalk radiating through their sandals. Just around the corner, a group of cruise ship passengers shuffled past from Mallory Square, their lanyards swinging in perfect synchronization.
Tess and Leah walked several blocks before Leah pointed toward a large house on the corner. A simple sign out front read "Paradise Harbor House," offering no explanation of its purpose. A woman sat on the porch, radiating a quiet authority that lingered in Leah’s mind. There was something about her.
"What do you think that place is?" Leah asked, breaking the silence. A pelican swooped overhead.
Tess glanced at her, adjusting her sunglasses. "What place?"
"The house with the blue sign, Paradise Harbor House."
Tess shrugged, her attention caught by a window display of handmade jewelry. "Probably a bed and breakfast or something. Everything here is either a bed and breakfast or a bar.”
Leah frowned, her curiosity piqued. "I don't think it's a bed and breakfast." She remembered the neat rows of chairs on the porch, the professional signage, the way the woman had studied her clipboard with such focus.
"Why not?"
"Because the woman on the porch looked…serious. Like she was running something important. Not like someone recommending breakfast spots to tourists."
Tess waved a hand dismissively, her bracelets jingling. "Maybe she was just bossing around the cleaning staff. Don't overthink it. We've got bigger things to worry about, like what we're going to wear tomorrow night."
But Leah couldn't shake the feeling that there was more to Paradise Harbor House than Tess's casual explanation. And for the first time in weeks, she felt a spark of curiosity that had nothing to do with bills or finances.
Leah sat at the tiny kitchen table, her laptop open to a half-finished spreadsheet of their expenses. Tess was curled up on the sofa with a glass of wine, scrolling through Instagram. The kitchen was quiet except for the faint hum of the air conditioner.
Through the windows, Leah could hear the distant sounds of Duval Street coming alive for the night. Music drifted in from multiple directions. Soon, they'd be part of that nightly ritual, serving drinks to people living out their vacation fantasies while trying to keep their own dreams afloat.
"What are you looking at?" Leah asked, not looking up from the screen where numbers refused to add up to anything promising.
"Just ideas," Tess said, the sofa creaking as she shifted position. "You know, fun stuff we could do to spice up our social media. Maybe drum up some side income. Our follower count isn't terrible."
"Spice it up how?"
"Oh, you know," Tess said vaguely, her voice taking on that dreamy quality that usually preceded an expensive idea. "Something trendy. Maybe we make videos of us trying weird Key West foods or giving margarita tutorials. We could start a series called 'Sunset Sisters' Tips and Sips.'"
Leah gave her a sidelong glance. "You want to be influencers now?" She thought of their previous attempts at social media stardom, including the disastrous "Keys to Fashion" blog that had resulted in maxed-out credit cards and a closet full of tropical print dresses they'd never worn.
"Why not? Everyone else is doing it. And we've got personality. Plus, now that we'll be working at Margarita Max's, we'll have insider content. People love behind-the-scenes stuff."
"We've got bills." Leah highlighted another row in her spreadsheet, watching the numbers flash red. "And I'm not sure Connie will appreciate us turning her bar into content."
Tess waved a hand, nearly spilling her wine. "Details. Besides, this could be our breakthrough moment. Picture it: 'From Corporate Life to Island Time: Two Sisters' Journey to Paradise.' It's practically a ready-made reality show."
"More like a cautionary tale," Leah muttered, but she couldn't help smiling. Even their failures had style thanks to Tess.
"Anyway, I'm calling it a night. Big day tomorrow." Tess stood, stretching like a cat. "Should we practice making margaritas? I think we still have some tequila from the 'Cocktails and Crafts' phase."
"I think we should save the tequila for after our first shift," Leah said wisely. "Something tells me we're going to need it."
“By the way, tell me again what Kaitlyn said about coming here,” Tess asked.
Leah shrugged, “Not much, only that she needed a place to stay and that she couldn’t wait to see us. It’s not the best timing now that we’ve got jobs.”
“She’s young, Leah. She doesn’t need us hovering to have a good time in Key West. She’ll be fine.”
As Tess disappeared into her room, Leah stared at the spreadsheet, her mind drifting back to Paradise Harbor House. Something about that house seemed more like an important Key West establishment than just a bed and breakfast. The woman's purposeful movements, the neat rows of chairs, the sense of order amidst the chaos of Key West—it all meant something. She just wasn't sure what.
She typed in the name online and found more about the building.
Paradise Harbor House: Hope and Shelter for Southern Florida Families. Leah wondered why she didn’t notice the proper name when she saw the building earlier, but now, it made sense why it didn’t look like a bed and breakfast to her.
She closed the laptop and stood, stretching her stiff shoulders. The kitchen walls seemed to close in around her, yellow paint glowing softly in the evening light. Their "Life's Better in Flip Flops" sign hung slightly crooked above the sink, a testament to their early days of decorating with more enthusiasm than skill.
Maybe tomorrow would bring answers—or at least a distraction from the ever-present weight of their dwindling funds. Either way, it would be an adventure. And with Tess around, adventures were never in short supply. The trick was surviving them with their dignity—and their bank account—intact.
Through the window, she could see Ernest the rooster walking away, no doubt going off to his nesting spot for the night.
For a brief moment she thought about calling their older sisters, Chelsea and Gretchen. It pained her to think that she and Tess would have to go crawling back to their sisters on Captiva Island looking for help. But, in time, if things didn’t improve, they’d have little choice.
Tomorrow, they'd start their new jobs as bartenders, adding another chapter to their increasingly complicated Key West story. But tonight, in the quiet of their tiny kitchen, Leah allowed herself to feel hope once again and put any thought of failure out of her mind.