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(Camera opens on a bustling street in Old Havana—colorful colonial buildings, classic 1950s cars cruising by, and the rhythmic beats of live salsa music floating through the air. Conan O’Brien stands in the middle of it all, wearing a straw hat that’s slightly too big, sunglasses, and a bright Cuban guayabera shirt, looking both excited and slightly overwhelmed.)
Conan O’Brien: (Grinning at the camera, arms wide open)
“Ladies and gentlemen, welcome to Cuba! That’s right—I have officially made my way to this incredible, beautiful, history-packed country for a 5-day adventure unlike any other. And let me tell you, I am completely unprepared for what’s about to happen.
Cuba is a land of contrasts—it’s where colonial mansions meet salsa-filled streets, where time slows down but the energy never stops, where every single person seems to know how to dance… except me.
So what are we doing here? We’re about to dive headfirst into the chaos, and I’m bringing along a dream team of celebrities, musicians, and complete troublemakers to help me survive.”
Meet the Squad:
(Quick montage of each celebrity arriving, looking way too cool for Conan.)
- Jack Black – Because someone needs to be louder than me.
- Shakira – Our official salsa and empanada expert.
- Carlos Varela – The legend of Cuban music, who will turn everything into a song.
- Matthew McConaughey – He’s here to spiritually guide us… whether we asked for it or not.
- Gordon Ramsay – Because we need someone to aggressively yell about food while secretly loving it.
- Pedro Pascal – The mysterious adventure guy, who will make every moment feel like an HBO series.
- Emma Stone – Who will spend half the time laughing at me and the other half trying to survive my dance moves.
- Ana de Armas – Our Cuban Hollywood royalty, here to help us not look like complete tourists.
- Ryan Reynolds – The only person here more sarcastic than me.
- Megan Thee Stallion – Bringing the energy, the attitude, and the dance moves I will never master.
- Will Smith – Because every trip needs one Hollywood motivational speech.
- Dua Lipa – Who will somehow make every single location look like a high-fashion music video.
And of course, we’ll be joined by Cuba’s best tour guides, storytellers, and—oh yeah—a ghost historian.
What to Expect?
(Cut to fast-paced montage of the trip—dancing in the streets, Conan nearly falling off a horse in Viñales, Gordon Ramsay dramatically throwing a mojito, Megan Thee Stallion leading a salsa party, and Ryan Reynolds smirking at the camera.)
This 5-day adventure is packed with:
✔ Classic car rides through Havana
✔ Dancing until I embarrass myself in Trinidad
✔ Getting lost in underground caves in Viñales
✔ Cuban cigars, pirate legends, and way too many mojitos
✔ Sunburns, salsa, and absolute chaos
(Cut to Conan standing dramatically on the Malecón, the ocean waves crashing behind him.)
So strap in, grab a strong coffee, and get ready for the ultimate Cuban adventure.
LET’S DO THIS! (Cue salsa music, camera zooms out as Conan attempts to dance, while a local Cuban woman shakes her head in disappointment.)
Day 1: Havana Hustle – Classic Cars, Cocktails & Colonial Charms
Setting:
The morning sun casts a golden hue over Old Havana, illuminating the cobblestone streets as the scent of brewing Cuban coffee wafts through the air. The colonial buildings, painted in vibrant blues, yellows, and reds, look like an oil painting come to life. Street musicians strum their guitars, their melodies blending with the distant laughter of locals and the rhythmic beat of Cuban drums. The city buzzes with life—vendors shout about fresh guavas and hand-rolled cigars, while vintage 1950s Chevrolets roll down the street like time machines from a lost era.
Scene 1: Plaza Vieja - A Grand Entrance
Tour Guide (El Fantasma de la Habana): (With a mischievous grin)
“Welcome to Havana, my friends. You may have heard of the plazas, but few know the underground tunnels beneath these streets. Some say they were used by pirates. Others say they lead to hidden treasures.”
Conan O’Brien: (Eyes widening, adjusting his sunglasses)
“Oh great, we’ve been here for five minutes, and we’re already in a real-life escape room.”
Jack Black: (Throws his arms up theatrically)
“ARRR, me hearties! Let’s go loot some Spanish gold!” (He twirls around and nearly knocks over a tray of empanadas from a nearby vendor.)
Vendor: (Laughing)
“Señor, you already have the treasure… it’s in the food!”
Shakira: (Grabbing an empanada, taking a bite, then dramatically closing her eyes)
“Mmhh! He’s right. This is gold.”
Carlos Varela: (Smirking, strumming his guitar)
“Ah, but do you know the secret of Plaza Vieja? Beneath our feet, the ghosts of revolutionaries still whisper. Some say if you walk here at midnight, you hear their footsteps…”
Conan: (Mock serious, whispering to Jack Black)
“I’m pretty sure those footsteps are just drunk tourists looking for their Airbnbs.”
Scene 2: El Capitolio & The Mystery of the Golden Diamond
The group strolls toward El Capitolio, Havana’s grand neoclassical building, its dome glistening under the Caribbean sun. Inside, a tour guide points to the gigantic 24-karat diamond embedded in the floor.
Tour Guide (El Fantasma):
“This is the zero-kilometer marker of Cuba. But the real mystery? The diamond was stolen in 1946 and mysteriously returned… no one knows how.”
Jack Black: (Leans in, whispers to Conan)
“Do we tell them I stole it? Or do we keep that between us?”
Conan: (Nods solemnly)
“We keep it. But if we ever need quick cash, we revisit this conversation.”
Shakira: (Pretending to investigate)
“You know, I bet the diamond whispered to someone in a dream and asked to be returned.”
Carlos Varela: (Plucks a few haunting notes on his guitar, then sings in a deep, mysterious tone)
“The lost diamond… it spoke of revolution… and in the night… it returned…”
Conan: (Looking directly at the camera, deadpan like in a late-night monologue)
“Ladies and gentlemen, you just witnessed a spontaneous Cuban folk song being born.”
Scene 3: La Bodeguita del Medio – Hemingway’s Favorite Spot
The group steps into the dimly lit bar, its walls covered in handwritten messages and signatures from past visitors. The air is thick with the scent of mint and lime as bartenders muddle mojitos with an effortless rhythm.
Tour Guide (El Fantasma):
“Hemingway once wrote, ‘My mojito in La Bodeguita, my daiquiri in El Floridita.’”
Conan: (Taking a sip of his mojito, eyes narrowing in exaggerated judgment)
“Alright, Hemingway, I’ll admit it… you knew what you were talking about.”
Jack Black: (Holding up his glass like a dramatic Shakespearean actor)
“To Papa Hemingway! The only man who could drink twelve of these and still write a literary masterpiece.”
Shakira: (Laughing, raising her glass)
“To the spirit of adventure!”
Carlos Varela: (Toasting in Spanish, then smirking at Conan)
“Welcome to Havana, my friend. But be warned: the city changes you.”
Scene 4: Revolution Square – The Iconic Moment
As the sun begins to set, the group arrives at Plaza de la Revolución, where Che Guevara’s massive mural looms over the square, casting a long shadow. The air feels charged with history, as if the very ground remembers every speech ever given here.
Conan: (Looking at Che Guevara’s face, arms crossed)
“I mean, this guy has one of the most iconic faces in history. He’s like the Elvis of revolutions.”
Jack Black: (Raising an imaginary microphone, belting out in an over-the-top rock voice)
“Viva la revoLUUUCIOOOOOON!!” (Nearby tourists actually start clapping.)
Shakira: (Nods, smiling)
“There’s something powerful about this place. You can feel the weight of history here.”
Carlos Varela: (Gesturing around him)
“It’s not just history. It’s our story. Every Cuban carries this square in their heart.”
Tour Guide (El Fantasma): (Suddenly lowering his voice, eyes darting left and right)
“…And now, let me show you something not in the history books. Follow me.”
Scene 5: The Malecón – Sunset & Classic Cars
The group walks along the Malecón, the salty sea breeze tousling their hair. Classic 1950s cars, painted in bubblegum pinks, deep blues, and fiery reds, cruise by as couples dance to the sounds of a live street band. The sky is a blend of fiery orange and dusky purple.
Conan: (Hands on hips, dramatically gazing at the ocean)
“Well, Jack, we survived Day 1. No pirate ghosts, no stolen diamonds, and we only embarrassed ourselves twelve times.”
Jack Black: (Nods thoughtfully)
“That’s what I call… a successful day.” (Pause) “Now, who wants to race vintage cars down the Malecón?”
Shakira: (Laughs, shaking her head)
“This is either the best idea… or the worst.”
Carlos Varela: (Strumming his guitar one last time)
“In Cuba… there is no wrong answer.”
Day 2: Viñales Vibes – Caves, Cigars & Countryside Magic
Setting:
The morning mist still lingers over Viñales Valley, where limestone mogotes (karst formations) tower over endless fields of tobacco and sugarcane. The scent of fresh earth and morning dew fills the air as the group’s vintage 1950s Chevy convertible rumbles along a dirt road, kicking up light dust as it moves through one of Cuba’s most picturesque rural landscapes.
Today is all about adventure, mystery, and Gordon Ramsay losing his patience.
Scene 1: Sunrise Over Viñales Valley
The group arrives at Los Jazmines Viewpoint, where the golden sunrise spreads over the valley, illuminating the rolling green fields below. A few farmers, or guajiros, ride past on horseback, tipping their hats as the smell of fresh-brewed Cuban coffee drifts from a nearby stall.
Tour Guide (Don Pepe – a rugged Cuban cowboy in his 60s, tipping his straw hat): (Grinning, hands on his hips)
“Señores, welcome to *Viñales Valley—land of the best cigars, the best coffee, and the slowest WiFi in the world.”
Conan O’Brien: (Sipping coffee, coughing violently)
“Oh my god, this coffee is like drinking molten lava.”
Matthew McConaughey: (Holding his cup, staring at the valley like a philosopher)
“This… this is what you call soul-healing scenery.”
Gordon Ramsay: (Taking a sip, nodding)
“Finally. A coffee that actually wakes you up instead of tasting like dishwater.”
Alexander Abreu: (Playing a soft melody on his trumpet, looking out over the valley)
“This is music, but in landscape form.”
Conan: (Nodding, adjusting his sunglasses)
“Great, I love that. But can we do music in sandwich form next? Because I’m starving.”
Scene 2: The Cueva del Indio – Underground River Adventure
The group steps into Cueva del Indio, where the temperature drops, and the sound of dripping water echoes through the massive rock formations. The air is thick with moisture and the scent of ancient stone. A small wooden boat awaits to take them through the underground river.
Tour Guide (Don Pepe): (Lighting a lantern, whispering dramatically)
“Many say this cave was used by runaway slaves and smugglers. Some say… it still holds secrets.”
Conan: (Leaning in, mock whispering to McConaughey)
“I think we’re the secret now. If we don’t make it out, tell my fans I was cool.”
McConaughey: (Stepping into the boat, smirking)
“Nah, brother. You’d haunt this place forever, making fun of the stalactites.”
Gordon Ramsay: (Crossing his arms, unimpressed as the boat floats into darkness)
“Brilliant. A floating cave tour, and no one even packed snacks.”
As the boat glides through the eerie underground river, torchlight flickers on ancient cave walls covered in prehistoric Taíno carvings.
Alexander Abreu: (Softly playing a melody on his trumpet, the sound bouncing off the cavern walls)
“Even the stones remember the music.”
Conan: (Looking around, eyes wide)
“Okay, that was way too poetic for a cave trip.”
As they reach the cave exit, a sudden burst of daylight blinds them, revealing a stunning jungle waterfall pouring into a crystal-clear pool.
Gordon Ramsay: (Finally impressed, sighing deeply)
“Alright. Now that’s a view.”
Scene 3: The Tobacco Farm – Rolling Cigars with Masters
The group arrives at a traditional tobacco farm, where golden leaves hang drying in a wooden barn. The earthy aroma of fresh tobacco fills the air as an elderly farmer, Don Rafael, expertly rolls a cigar with slow, precise movements.
Don Rafael (smiling, holding up a finished cigar):
“Making a Cuban cigar is like making a great song—it takes patience, tradition, and a little bit of soul.”
McConaughey: (Rolling a cigar, nodding seriously)
“This… this is an art form.”
Gordon Ramsay: (Inspecting his own cigar, shaking his head)
“Well, mine looks like a rolled-up piece of disappointment.”
Conan: (Holding up his cigar, completely uneven and misshapen)
“Mine looks like a 3-year-old tried to make a burrito.”
Alexander Abreu: (Laughing, lighting his cigar, exhaling slowly)
“Doesn’t matter how it looks. Only how it smokes.”
Conan: (Taking a puff, coughing dramatically)
“Oh god. I think I just aged 10 years.”
Scene 4: The Mural de la Prehistoria – Cuba’s Strangest Artwork
The group stands before the massive, brightly painted rock mural, where dinosaurs, giant snails, and ancient humans are splashed across a limestone cliff.
Conan: (Squinting, confused)
“So, someone looked at a perfectly good mountain and thought… you know what this needs? A NEON GREEN T-REX.”
McConaughey: (Admiring it, arms crossed)
“I respect it. Bold choices, no hesitation.”
Gordon Ramsay: (Shaking his head, frustrated)
“This is the worst color palette I’ve ever seen. It looks like a melted bag of Skittles.”
Alexander Abreu: (Grinning, leaning on his trumpet)
“But it’s Cuba, my friends. We don’t do boring.”
Scene 5: Sunset Horseback Ride Through Viñales
As the sun dips behind the limestone cliffs, the group rides horseback through endless green fields, the air thick with the scent of mango trees and wildflowers. The only sounds are hoofbeats, the distant song of crickets, and the occasional laugh from Conan struggling to stay on his horse.
Conan: (Holding onto the reins for dear life)
“This is NOT like riding a rental scooter in LA.”
Gordon Ramsay: (Riding smoothly, looking over at Conan, smirking)
“I didn’t know horses could sense fear.”
McConaughey: (Riding effortlessly, looking at the sunset)
“You know, there’s something about this moment… a man, his horse, the open land…”
Conan: (Rolling his eyes, mock dramatic)
“Oh no. He’s about to give a speech.”
Alexander Abreu: (Playing a final, slow tune on his trumpet as the sun sets)
“Viñales doesn’t speak. It sings.”
As the last golden light disappears behind the mogotes, the group rides off toward the horizon, the sound of laughter, music, and Conan yelling at his horse echoing into the Cuban night.
Day 3: Colonial Cuba – Cienfuegos Elegance & Trinidad Rhythms
Setting:
The group sets off from Viñales at dawn, driving through the lush countryside in a vintage sky-blue 1950s Chevrolet. As they approach Cienfuegos, the scenery shifts—wide coastal boulevards, elegant French-style mansions, and the tranquil blue of Cienfuegos Bay.
Later, they head south to Trinidad, where time seems frozen in the 18th century—cobblestone streets, pastel-colored colonial houses, and horse-drawn carts clattering down narrow alleys. The golden afternoon light bathes Plaza Mayor, where locals sip coffee on their balconies, watching the day unfold.
Today, the group will encounter ghosts, pirates, questionable dance moves, and an unexpected romantic revelation.
Scene 1: Cienfuegos’ Palacio de Valle – The Haunted Mansion by the Bay
The group stands before Palacio de Valle, an opulent Moorish-style mansion with intricate archways, a rooftop terrace, and whispers of pirate legends. The breeze from the bay carries the scent of salt and mystery.
Tour Guide (Captain Miguel – a dramatic storyteller who may or may not be an actual pirate): (Grinning, lowering his voice for effect)
“This palace… it holds secrets. Built by a sugar baron, but some say, his fortune was cursed. Ghosts walk these halls, my friends.”
Conan O’Brien: (Glancing around, mock serious)
“Well, if I see a ghost, I’m charging them for an interview.”
Emma Stone: (Shivering exaggeratedly, rubbing her arms)
“I don’t know, guys… This place definitely has haunted mansion vibes.”
Pedro Pascal: (Smirking, leaning against a pillar)
“So what’s the over-under on Conan screaming first?”
As they step inside, the temperature seems to drop. The walls are covered in intricate carvings, gold trim, and mirrors that reflect the candlelight in eerie ways.
Ana de Armas: (Looking into one of the mirrors, tilting her head)
“I swear… I just saw something move behind me.”
Conan: (Turning abruptly, eyes wide)
“Okay, NOPE. I am not getting possessed today.”
A gust of wind suddenly slams a door shut behind them. The room falls silent.
Pedro Pascal: (Looking at Conan, deadpan)
“I think it’s too late.”
Scene 2: Plaza José Martí – Cienfuegos’ Timeless Elegance
Escaping the “haunted” palace, the group finds themselves in Plaza José Martí, a grand colonial square framed by neoclassical architecture and shady palm trees. A local street musician strums a guitar, his voice drifting through the warm afternoon air.
Tour Guide (Captain Miguel, now smiling warmly):
“This, my friends, is the heart of Cienfuegos. Built with French elegance, it has been called 'The Paris of the Caribbean.’”
Emma Stone: (Looking around, nodding approvingly)
“I mean, yeah. I get it. If I had to be stuck in one era forever, I’d pick this one.”
Ana de Armas: (Smirking, playfully nudging Conan)
“So, Conan, when are you buying a mansion here?”
Conan: (Nodding dramatically, hands on hips)
“Oh, I already made an offer. Just waiting for the ghosts to accept.”
Scene 3: Trinidad – The City Where Time Stands Still
Arriving in Trinidad, the group steps into what feels like a movie set—Spanish colonial buildings with wrought-iron balconies, brightly painted facades, and cobblestone streets that have existed for centuries.
A horse-drawn cart rattles past as they reach Plaza Mayor, the town’s most picturesque square. Sunlight filters through bougainvillea-covered archways, casting long golden shadows.
Tour Guide (a Trinidad local, Señora Isabel, elegantly dressed in a flowing white dress, speaking in a melodic voice):
“Ah, welcome to Trinidad. Here, the past and present are one. The music, the people… the stories never leave.”
Pedro Pascal: (Taking a deep breath, admiring the view)
“This place is ridiculously cinematic. I feel like I’m in a period drama.”
Emma Stone: (Gesturing at the cobblestone streets, wobbling slightly in her shoes)
“Okay, but how did people survive in heels back then?”
Scene 4: Museo Romántico – Love & Scandal in Colonial Cuba
Inside Museo Romántico, an opulent mansion filled with 18th-century furniture, chandeliers, and old love letters, the group listens as Señora Isabel recounts a story.
Señora Isabel: (Smiling mysteriously)
“This house belonged to a noblewoman whose love was forbidden. They say, on some nights, you can still hear her… waiting for him.”
Ana de Armas: (Smirking, crossing her arms)
“Classic. Nothing like a tragic love story to keep a place interesting.”
Conan: (Looking at Pedro, mock serious)
“Alright, who’s falling in love today?”
Pedro Pascal: (Leaning casually against a velvet chair, smirking)
“I mean… we’re in the perfect setting.”
Emma Stone: (Dramatically clutching her chest, gasping)
“Pedro, no! We mustn’t! Society won’t allow it!”
Conan: (Pretending to wipe away a tear)
“This love story is already better than most movies.”
Scene 5: Casa de la Música – A Salsa-Fueled Farewell
As night falls, the group finds themselves at Casa de la Música, an open-air courtyard where a live Cuban band plays rhythmic salsa beats. The air is thick with laughter, clinking mojito glasses, and the infectious sound of drums and trumpets.
Emma Stone: (Looking around nervously)
“Okay, I have a confession… I cannot dance.”
Ana de Armas: (Grinning, grabbing her hand)
“Then tonight, you learn.”
Pedro Pascal is already on the dance floor, spinning a local dancer with ease, while Conan… struggles.
Conan: (Trying to follow the rhythm, wildly flailing his arms)
“This is an athletic event!”
Emma Stone: (Laughing hysterically)
“Conan, you look like a malfunctioning robot!”
The night spirals into joyful chaos—drinks flow, laughter fills the air, and the group finds themselves completely lost in the magic of Cuba.
As the music swells, they raise their glasses for one final toast in Trinidad.
Conan: (Smiling, raising his glass high)
“To **Cuba—the land where time slows down, music never stops, and apparently, I am the worst dancer in history.”
Day 4: Varadero Bliss – Sun, Sand & Snorkeling in Paradise
Setting:
The group leaves the cobblestone streets of Trinidad behind, trading history for pure beach paradise. As they approach Varadero, the landscape transforms—crystal-clear turquoise waters, powdery white sand, and palm trees swaying lazily in the warm Caribbean breeze. The air is thick with the scent of salt, coconut sunscreen, and freshly grilled seafood.
Today’s mission? Relax, swim, drink, and create total chaos on Cuba’s most famous beach.
Scene 1: Playa Varadero – A Grand (Chaotic) Arrival
A bright yellow 1950s convertible pulls up to the beach entrance. Ryan Reynolds is in the driver’s seat, wearing sunglasses and smirking like he’s filming a car commercial.
Ryan Reynolds: (Looking at the ocean, nodding approvingly)
“Alright. I’ll admit it… this is paradise.”
Conan O’Brien: (Stepping out, instantly sinking ankle-deep in the sand)
“Oh wow, so soft! It’s like stepping on a cloud… that burns your feet.”
Megan Thee Stallion: (Adjusting her sunglasses, grinning)
“This is the kinda place where I’m never leaving.”
Leoni Torres: (Looking out at the waves, nodding)
“Cuba’s beaches… they don’t just exist. They sing.”
Ryan Reynolds: (Turning to Conan, mock serious)
“So what’s the over-under on you getting sunburned in the next hour?”
Conan: (Rolling up his sleeves, exposing shockingly pale skin)
“Oh, buddy, I give it ten minutes.”
They grab hammocks under a thatched-roof cabana, sip on coconut cocktails, and take in the unbelievable beauty of the beach.
Scene 2: Catamaran Cruise & Snorkeling Adventure
The group boards a sleek white catamaran, sailing across glass-like turquoise water. A warm breeze whips through their hair, and a crew member hands out snorkeling gear as they head toward a hidden coral reef.
Ryan Reynolds: (Holding up his snorkel, shaking his head)
“I just want to be clear—if I see a shark, I’m using Conan as bait.”
Conan O’Brien: (Scoffing, adjusting his snorkel mask)
“Wow, the betrayal.”
Megan Thee Stallion: (Laughing, pulling on her flippers)
“Conan, you better learn to swim like your life depends on it.”
Leoni Torres: (Smiling, strumming a few notes on his guitar before setting it down)
“In Cuba, the ocean is not just water. It’s a world of music below the waves.”
They jump into the crystal-clear water, where the coral reefs are alive with neon-colored fish, swaying sea fans, and an occasional sea turtle gliding by.
Conan: (Muffled through his snorkel, gesturing wildly at a massive school of fish)
“MMMMPHMMM!!!” (Translation: “OH MY GOD, LOOK AT THIS!”)
Ryan Reynolds: (Calmly floating, staring at a stingray swimming past)
“I feel like this is what peace looks like.”
Megan Thee Stallion: (Spinning underwater, grinning through her mask)
“This is the most beautiful thing I’ve ever seen.”
Scene 3: Lunch at Xanadu Mansion – Ocean Views & Fine Dining
Back on land, they arrive at Xanadu Mansion, a historic estate built on a cliff overlooking the ocean. The scent of freshly grilled lobster, garlic butter, and Cuban spices fills the air.
Waiter: (Setting down a platter of fresh seafood and chilled mojitos)
“Señores, welcome to the best ocean view in Cuba.”
Conan: (Sipping his mojito, sighing dramatically)
“I don’t even need a house. I’ll just live right here.”
Ryan Reynolds: (Cutting into his grilled lobster, nodding)
“This is actually… unfairly good.”
Megan Thee Stallion: (Taking a bite, closing her eyes in bliss)
“I need this chef in my life.”
Leoni Torres: (Taking a sip of rum, smiling)
“You see, my friends… Cuba is not just a place. It is a rhythm.”
Scene 4: Parque Josone – Lazy Lagoon & Paddle Boats
After lunch, they head to Parque Josone, a lush green oasis with a scenic lagoon, where flamingos stand in shallow waters and small paddle boats float by.
Ryan Reynolds: (Looking at the paddle boats, smirking)
“Alright, I challenge you all to a boat race.”
Conan: (Stretching dramatically)
“Oh, it’s ON.”
The race begins—Ryan and Megan vs. Conan and Leoni. Chaos ensues.
Megan Thee Stallion: (Laughing, paddling furiously)
“Ryan, you BETTER keep up!”
Conan: (Sweating, dramatically paddling in the wrong direction)
“HOW AM I LOSING?! Leoni, DO SOMETHING!”
Leoni Torres: (Casually strumming a song on his guitar instead of paddling)
“I am doing something… I’m making this moment poetic.”
Ryan and Megan win by a mile, while Conan and Leoni drift into some reeds.
Conan: (Slumped in his boat, panting)
“This was the worst idea.”
Scene 5: Beachfront Nightlife – Fire Dancers & Farewell Drinks
As night falls, the group gathers at a beachfront bar, where torches glow, a live Cuban band plays salsa rhythms, and fire dancers perform under the stars.
Bartender: (Handing out rum cocktails, smiling)
“Tonight, we toast to Cuba.”
Conan: (Raising his glass, grinning)
“To Cuba—the place where I lost a boat race, got sunburned, and nearly became shark bait… but also had the best time of my life.”
Megan Thee Stallion: (Clinking glasses with everyone)
“To the craziest, most beautiful adventure.”
Ryan Reynolds: (Smirking, sipping his drink)
“To Cuba, where even Conan found happiness.”
Leoni Torres: (Smiling, strumming his guitar one last time)
“And to the music that never stops.”
As the waves crash against the shore and the fire dancers twirl under the moonlight, the group laughs, dances, and drinks the night away, lost in the magic of Cuba.
Day 5: Havana Farewell – Art, History & One Last Mojito
Setting:
The final day in Cuba begins in Havana, where the streets are alive with the sounds of rumba music, morning markets, and the distant hum of classic cars rolling past colorful colonial buildings. The scent of strong Cuban coffee and freshly baked pastries fills the air as the group sets off for one last day of adventure.
Today’s mission? Art, history, and one last unforgettable night in Havana.
Scene 1: Fusterlandia – A Surreal Mosaic Wonderland
The group arrives at Fusterlandia, a bizarre, colorful dreamscape of mosaics, sculptures, and surreal street art created by Cuban artist José Fuster. Every inch of the neighborhood is covered in bright swirling tiles, abstract figures, and hidden symbols.
Will Smith: (Looking around, wide-eyed)
“Okay, this is giving me serious ‘Fresh Prince intro’ vibes.”
Dua Lipa: (Snapping a photo, laughing)
“This place is like a fever dream… but make it art.”
Conan O’Brien: (Gesturing at a giant rooster sculpture wearing a crown)
“I don’t know who designed this… but they were definitely having the time of their life.”
Tour Guide (Abuela María – an elderly Cuban woman who knows everything about Havana’s secrets): (Smiling, hands on hips)
“Fuster says this place is a love letter to Cuba. Every tile tells a story.”
Will Smith: (Pointing to a wall with a giant eye mosaic)
“This one says… ‘Conan is watching you.’”
Conan: (Deadpan, crossing arms)
“Good. I like my art with a little paranoia.”
Scene 2: Hemingway’s Finca Vigía – A Writer’s Retreat
Next stop: Hemingway’s house, Finca Vigía, a hilltop estate surrounded by lush gardens, where the legendary writer lived and wrote some of his greatest works. Inside, his vintage typewriter still sits on the desk, his books line the walls, and his fishing trophies stare down from the shelves.
Tour Guide (Abuela María, whispering mysteriously):
“Some say Hemingway’s spirit never left this house.”
Conan: (Pretending to knock on the walls)
“Papa Hemingway? If you’re still here, give us a sign.”
Dua Lipa: (Examining Hemingway’s typewriter, running her fingers over the keys)
“You can almost feel the stories waiting to be told.”
Will Smith: (Looking at Hemingway’s old liquor cabinet, raising an eyebrow)
“This man had more rum than a nightclub.”
Suddenly, a gust of wind blows through the house, knocking over an empty glass.
Conan: (Eyes widening, turning to the guide)
“Okay, WHAT WAS THAT?”
Tour Guide (smiling knowingly):
“Ah… he knows you’re here.”
Will Smith: (Backing away, laughing nervously)
“Ohhh nope. I’m not tryna get haunted today.”
Scene 3: Cojímar – A Seaside Escape
The group takes a short drive to Cojímar, a quaint fishing village by the sea, where Hemingway found inspiration for The Old Man and the Sea. The ocean stretches endlessly, and small fishing boats bob gently in the harbor.
Dua Lipa: (Taking in the view, smiling)
“This place… it feels untouched by time.”
Conan: (Holding a seashell to his ear, nodding seriously)
“Yes. I can hear Hemingway whispering.”
Will Smith: (Squinting at Conan)
“You sure that’s not just the wind?”
Eusebio Leal (The Ghostly Historian of Havana, appearing out of nowhere): (Clears throat, speaking in a deep, poetic voice)
“Hemingway did not just write… he lived. His soul was stitched into Havana’s very essence.”
Conan: (Leaping backward in shock)
“OH MY GOD. WHY DO CUBAN HISTORIANS ALWAYS APPEAR OUT OF NOWHERE?”
Dua Lipa: (Laughing, nodding at Eusebio)
“Alright, ghost man, since you’re here—tell us, what would Hemingway think of modern Havana?”
Eusebio Leal (Ghost Mode, nodding solemnly):
“He would say Havana remains unbroken. It evolves, but its spirit endures.”
Will Smith: (Nodding respectfully)
“Alright, respect. That’s deep.”
Scene 4: The Malecón at Sunset – A Final Walk
As the sun begins to dip below the horizon, the group strolls along the Malecón, Havana’s famous seaside boulevard. The sky blazes in hues of orange and pink, while classic 1950s cars cruise by, honking cheerfully. Musicians play soft bolero melodies as the waves crash against the seawall.
Conan: (Sighing, hands in pockets)
“This is it, huh? The last sunset in Cuba.”
Will Smith: (Looking at the ocean, arms crossed)
“Yeah, man. Cuba gave us everything. The music, the history, the chaos…” (Smirking) “And your terrible dance moves.”
Dua Lipa: (Sipping a mojito, laughing)
“To Cuba, the land that changed us.”
Conan: (Raising his glass, grinning)
“To us… surviving Cuba.”
Scene 5: Farewell Drinks in Old Havana – The Final Toast
The group gathers at a rooftop bar in Old Havana, where string lights glow, the music flows, and the city twinkles beneath them.
Leoni Torres appears, serenading the group with a final soulful Cuban ballad.
Eusebio Leal (The Ghost, raising a glass):
“Havana… never says goodbye. It only waits… for your return.”
Conan: (Nodding, lifting his drink, voice softer now)
“To the people we met. The places we saw. And the city that… felt like home.”
As the last note of music fades into the night, the waves crash, the laughter lingers, and Havana… lives on.
Final Reflection – Farewell to Cuba
(Camera fades in to Conan O’Brien standing along the Malecón, the sun setting behind him in a fiery mix of orange, pink, and deep violet. The ocean waves crash gently against the seawall, and the distant sound of a Cuban street band fills the air. Conan, wearing his slightly oversized straw hat and looking both sentimental and exhausted, takes a deep breath and turns to the camera.)
Conan O’Brien: (Smiling, shaking his head slightly, as if still processing everything.)
“Well, folks… that’s it. Five days. Five cities. Countless mojitos. And what do we have to show for it? A bunch of hilarious misadventures, new dance moves that no one asked for, and a deep, undeniable love for Cuba.
Before coming here, I thought I knew what Cuba was all about—classic cars, cigars, beaches, salsa music. And yes, it’s all of those things. But what I didn’t expect was for Cuba to feel like a story I never wanted to end.
What Did We Learn?
- In Havana, we learned that history isn’t just something you read—it’s something you feel. And also, that Jack Black should never be allowed behind the wheel of a classic car.
- In Viñales, we learned that time moves slower, cigars are an art form, and Gordon Ramsay has strong opinions about farm food.
- In Cienfuegos, we found elegance, pirate legends, and undeniable proof that Pedro Pascal may have secretly lived in the 1800s.
- In Trinidad, we learned that cobblestone streets were designed specifically to destroy my ankles, salsa is a competitive sport, and I am still, by far, the worst dancer in Cuba.
- And in Varadero, we learned that Ryan Reynolds is an elite snorkeler, Megan Thee Stallion can turn any beach into a music video, and no mojito tastes better than the one you drink barefoot in the sand.
But the biggest lesson of all? Cuba doesn’t say goodbye. It just waits for you to come back.
The Final Toast
(Conan raises a glass of rum, staring out at the ocean, the waves reflecting the last golden light of day.)
“To the people we met. The stories we shared. The places that made us laugh, dance, and maybe even reflect a little. And to Cuba—a country that doesn’t just exist, but moves, breathes, and sings.”
(He clinks glasses with Will Smith, Dua Lipa, and Leoni Torres, who have quietly joined him on the Malecón. The camera zooms out as the group watches the sunset, the sounds of distant music and laughter floating into the Havana night.)
Short Bios:
- Conan O’Brien – Legendary comedian, late-night host, and self-proclaimed terrible dancer, known for his sharp wit and ability to make any situation hilariously awkward.
- Jack Black – Actor, musician, and human hurricane of unfiltered energy, ready to bring chaos, comedy, and unexpected musical performances.
- Shakira – Global pop icon, dance queen, and the official expert in all things salsa, prepared to show Conan exactly how not to move his hips.
- Carlos Varela – Cuban singer-songwriter and poetic storyteller, ready to turn every moment into a song and give the trip its perfect soundtrack.
- Matthew McConaughey – Oscar-winning actor, philosopher of chill, and the guy who will turn any situation into a deep life lesson.
- Gordon Ramsay – World-renowned chef, king of brutal honesty, and most likely to lose patience when served under-seasoned food.
- Pedro Pascal – The ultimate cool adventurer, known for his effortless charm, mysterious past-life vibes, and ability to make every moment feel like an HBO drama.
- Emma Stone – Award-winning actress and professional sarcasm expert, here to both laugh at Conan and attempt to survive the trip without breaking an ankle.
- Ana de Armas – Cuban-born Hollywood star and effortlessly glamorous tour guide, making sure the group doesn’t look like complete tourists.
- Ryan Reynolds – Actor, entrepreneur, and the only person capable of out-sarcasming Conan, guaranteeing that no moment will go unroasted.
- Megan Thee Stallion – Rap superstar and queen of energy, ready to turn every street, dance floor, and beach into an instant party.
- Will Smith – Hollywood icon, master of charisma, and the guy most likely to turn any moment into an epic, motivational speech—whether you asked for it or not.
- Dua Lipa – International pop sensation, effortlessly cool, and the person who will make every location look like a Vogue cover shoot.
- Leoni Torres – Cuban music legend with the voice of a dream, here to serenade the group and capture the soul of Cuba in every song.
- Eusebio Leal (The Ghostly Historian of Havana) – Legendary historian and mysterious storyteller, known for appearing out of nowhere with deep, poetic wisdom.
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