Cuba has long called to me.
It started with Havana, that moody 1990 film where Robert Redford plays a gambler drawn into revolution—and into the arms of Lena Olin’s enigmatic, defiant freedom fighter. Raul Julia, unforgettable as her husband, brings layers of elegance and tragedy to the story. The romance lingers, like smoke in the air.
Then, of course, there’s Hemingway. He lived and wrote at Finca Vigía, just outside Havana. For Whom the Bell Tolls and The Old Man and the Sea—both were written there. He wasn’t alone. Third wife Martha Gellhorn (watch Hemingway & Gellhorn, with Clive Owen and Nicole Kidman on MAX) and fourth wife Mary Welsh also walked those halls. Graham Greene’s Our Man in Havana—one of my favorite spy novels—adds another layer to the mystique.
As a former ballerina, I’ve always been drawn to Cuba’s extraordinary legacy in classical ballet. It’s a global powerhouse—celebrated for its emotionally expressive dancers, breathtaking technique, and deep artistic discipline. Two of my favorites, Xiomara Reyes and José Manuel Carreño, both trained in Cuba before gracing the stage at American Ballet Theatre. (He even had a place on my wall for years, alongside the icons of that early aughts ballet era.)
And the music. Buena Vista Social Club plays in the background of my memories, even though I haven’t set foot there. Yet.
Cuba also shaped history. I remember studying the explosion of USS Maine, Hearst’s and Pulitzer’s yellow journalism, and the resulting Spanish-American War. Four months reshaped empires: Puerto Rico, Guam, and the Philippines were all acquired by the USA. And Cuba was, for a time, a U.S. protectorate. The echoes remain.
Today, Cuba remains under communist rule, led by Miguel Díaz-Canel. Press freedoms are limited, yet culture—art, music, dance, poetry—still bursts through. Yes, Americans can visit, typically under the “Support for the Cuban People” category. Europeans need a tourist card.
And everyone needs a curious spirit.
I nearly went once, over a decade ago. A client’s recent inquiry pulled me back to the idea — and the possibilities are extraordinary.
Think Art Deco facades and Neoclassical splendor, Brutalist geometry beside Moorish arches. Old Havana, a UNESCO World Heritage site, is just the beginning. Head west to Viñales, where emerald valleys meet limestone cliffs and local farmers hand-roll cigars as their ancestors did. It’s wild. Lush. Untamed. Ready.
Step into a reimagined Cuba—sun-warmed, stylish, and irresistibly alive. Glide through Havana in a vintage convertible, salsa drifting from an open door. Sip a mojito by candlelight. And trace Hemingway’s footsteps. Dance until the music tells you to stop.
For the traveler who craves substance and soul, elegance and authenticity, your Cuban story awaits.
Havana‘s Classic Cars
There is no grander introduction to Havana than from the plush interior of a vintage automobile. These gleaming American classics from the 1950s are more than mere vehicles; they are living testaments to Cuba’s enduring spirit. As your chauffeur navigates past pastel-hued facades, bustling plazas, and the iconic Malecón, the city’s inherent allure reveals itself in every turn.
But your journey into Havana’s heart extends beyond the open road. You’ll be able to access a hidden workshop, a sanctuary where master Cuban mechanics, fueled by ingenuity and a profound respect for tradition, breathe life into these automotive legends. Their stories are a testament to resilience, offering an unfiltered glimpse into a culture that transforms constraint into captivating artistry.
Unwind and Indulge The Cuban Way
As twilight descends, retreat to your hotel, where the day gracefully culminates. Indulge in the finest Cuban cigars, and savor aged rum or sip fresh mojitos crafted precisely to your preference. Envision yourself beside the pool, a live band weaving a tapestry of sound under the starlit sky, the evening unfolding at your leisure—no schedules, no haste.
Whether it’s an exquisite dinner prepared by your private chef, an impromptu game of poker, or a refreshing midnight swim, the ambiance is unmistakably Cuban: serenely luxurious and vibrantly alive.
Our Top 3 Handpicked Stays:
Casa Italia
An elegant fusion of Cuban soul and Italian design, Casa Italia spans two meticulously restored mansions where every detail—from the Murano lighting to the artisanal pasta—is sourced from Italy. Its lush courtyard and serene pool area offer a refined, tranquil escape, making it one of Havana’s most coveted boutique stays.
La Reserva:
Step inside this thoughtfully restored mansion and you’ll find an art-filled haven centered around a serene interior courtyard. The hotel’s signature restaurant, La Bodega, is a culinary standout, serving locally inspired fare in an atmosphere that feels both intimate and cosmopolitan.
Paseo 206
Charming and contemporary, Paseo 206 is the creation of a Cuban-Italian couple whose love story infuses every corner of this intimate boutique hotel. Its restaurant, Eclectico, blends old-world warmth with fresh Havana energy, offering an inviting indoor-outdoor setting ideal for long, flavorful meals and spirited conversation.
Viñales, Where Time Stands Still
A mere few hours beyond the city’s captivating embrace lies Viñales, a landscape so cinematic it blurs the line between reality and dream. Here, emerald valleys cradle majestic mogotes, inviting you to explore on horseback, scale dramatic limestone cliffs, or simply absorb the tranquility with a fine cigar in hand. This magical valley is quite the destination for adventure!
At an intimate, private tobacco farm, witness master artisans at work, their hands expertly rolling cigars using techniques passed down through generations. These are stories woven with threads of land, family, and craftsmanship, deeper than any guidebook could ever capture. A lavish countryside feast awaits, featuring a succulent whole roast pig, farm-fresh produce, and chilled beverages, all served with a warmth that is both unpretentious and profoundly personal.
A Private Yacht Affair
Should the call of the ocean beckon, trade the verdant valleys for the azure expanse of the Caribbean.
Aboard your private catamaran, set sail for the pristine white sands of Cayo Blanco. With an open bar at your disposal, a dedicated crew attending to your desires, and the gentle breeze caressing your skin, the day unfolds in a sequence of idyllic moments: snorkeling amidst vibrant coral reefs, enchanting encounters with playful dolphins, and a freshly grilled seafood feast served on a secluded, postcard-perfect beach.
This is not a collective excursion; it is your vessel, your curated soundtrack, your tranquil pace.
Echoes of Hemingway
Step through the gates of Finca Vigía, and you’ll feel as though you’ve crossed into Ernest Hemingway’s private world—preserved in time, rich with presence. From 1940 until his departure in 1960, this hilltop estate just outside Havana served as Hemingway’s sanctuary, the place where his literary genius flourished and his passions were lived out in full. Remarkably, the interiors remain almost exactly as he left them, creating a deeply personal, near-mythic atmosphere—a living time capsule of a legendary life.
While entry into the house itself is not permitted, large open windows and doors offer an uncannily intimate view inside. You’ll glimpse his well-worn typewriter, still poised atop a shelf, the walls lined with books, and the quiet echoes of a writer’s daily rhythm. Outside, wander the tropical grounds to find Pilar, his beloved fishing boat, resting under a pavilion, and pause at the small pet cemetery—each marker a testament to Hemingway’s profound love for animals.
Finca Vigía is more than a historic home—it’s a portal into the soul of a man whose legacy still pulses through the pages of 20th-century literature.
Culinary Artistry
Cuba’s culinary landscape is undergoing a quiet, yet profound, revolution. Each morning commences with a personalized breakfast—a vibrant array of tropical fruits, freshly baked breads, and rich Cuban coffee. From there, every meal becomes an exploration.
Sip bespoke cocktails on a panoramic rooftop terrace, once an oil factory, now a beacon of modern design. Savor authentic flavors at a bustling café in Old Havana, surrounded by the convivial spirit of local life. Whether it’s gourmet sophistication or heartfelt home-cooked fare, dining in Cuba is an act of connection — to culture, to history, to the fleeting beauty of the present moment.
Boxing with the Spirit of Havana
Step into Rafael Trejo Boxing Gym, Havana’s open-air temple to one of Cuba’s most celebrated sports. Tucked into the heart of Old Havana, this storied gym pulses with the grit, rhythm, and discipline that have shaped generations of world-class Cuban boxers. Here, you don’t just observe—you feel the thrum of gloves on leather, the bark of coaches calling out drills, and the quiet intensity of young fighters chasing greatness.
Whether you’re stepping into the ring for a training session or simply soaking in the atmosphere, this is more than a workout—it’s a front-row seat to Cuba’s fierce pride, athletic excellence, and enduring passion for the sweet science.
Inside the Studio: A Private Encounter with Cuba’s Creative Soul
Venture beyond the surface of Havana and into the heart of its vibrant creative scene through a rare, intimate encounter with two of Cuba’s most compelling contemporary artists. In their private studios—often tucked behind unassuming façades—you’ll witness their process unfold in real time: brush strokes on canvas, sculpted forms taking shape, bold colors echoing the rhythm of the streets.
This is not a gallery visit. It’s a conversation — about inspiration, heritage, resistance, beauty, and the daily life of an artist in Cuba. Through their stories and their work, you’ll gain a richer, more nuanced understanding of Cuba’s dynamic cultural identity—and leave with more than memories. You’ll leave with a connection and a deep appreciation of Cuban art.
Beyond the Itinerary
This is far from a standard mass-market itinerary or a fleeting highlight reel. It’s a meticulously curated, deeply immersive experience, conceived for those who cherish privacy, profound cultural engagement, and effortless luxury. You will enjoy unparalleled insider access, bespoke touches, and the absolute freedom to shape your days precisely as you desire.
While Cuba may not boast the overt opulence of more conventional luxury destinations, its true richness lies in its boundless authenticity, captivating rhythm, and indomitable soul. When paired with our meticulous planning and elevated service, Cuba transforms into an unparalleled playground for the discerning traveler — one who seeks not merely beautiful scenery, but a profound and captivating story to tell.
Ready to Write Yours?
Whether you yearn for a serene escape with cherished friends, a captivating romantic interlude, or a cultural deep dive unlike any other, Cuba extends an irresistible invitation. Allow us to ensure your answer is nothing less than exquisitely styled.
Let us orchestrate your next extraordinary escape.
Private experiences. Seamless logistics. Unforgettable moments.
This is luxury redefined, Cuba-style.
