Why We Travel: Introducing Oscar’s Odyssey
Launching this journal feels both like a beginning and a return.
For decades I have designed journeys to Cuba and beyond—programs that bring travelers not only to destinations, but into dialogue with the soul of a place. With Oscar’s Odyssey, my aim is simple: to offer travel that is culturally rich, intellectually curious, and profoundly human. I write this not only as a guide, but as someone who was born and raised in Cuba and left the island at twenty. Returning as an adult, after a life abroad, I see Cuba with two sets of eyes: those of a local who remembers its rhythms and struggles, and those of a traveler who can step back and see possibility where fatigue often prevails. Where neighbors might see a derelict structure as collapse, I see the promise of restoration. Where scarcity drains patience, I glimpse creativity waiting to surface. This dual perspective—born of leaving and returning—is what I share with my travelers: not naïve optimism, but a deliberate choice to read the glass as half full.
This blog is not simply an announcement of trips or a calendar of departures. It is an ongoing conversation: about Cuba’s past, its present, and the directions in which the island moves. About art and the forces that shape it. About architecture as cultural memory. About women, religion, politics, and the elusive ways in which culture defines itself in moments of transition. It is here that we will share stories that go beyond itineraries—stories that explain why travel matters. Cuba remains one of the most fascinating and misunderstood places in the Americas. Its contradictions are part of its identity: a nation where revolutionary history meets contemporary art, where colonialplazas coexist with modernist suburbs, and where scarcity often breeds extraordinary creativity.
For many Americans, one question lingers: Can we travel legally to Cuba? The answer is yes. Despite shifting administrations and regulations, U.S. law still allows travel under the category Support for the Cuban People. This framework requires travelers to engage directly with Cuban citizens in the private sector—artists, entrepreneurs, restaurateurs, scholars, and community leaders—rather than with government-run institutions. Far from being a limitation, this demand enriches the journey. It insists on depth and meaningful contact. It is not tourism for tourism’s sake; it is travel as cultural engagement. At Oscar’s Odyssey, we design programs that combine history, art, religion, politics, and lived experience. A journey should not simply show you places, but reveal the forces that made them what they are.
Faith has always been one of Cuba’s deepest cultural foundations. Catholic traditions intertwine with Yoruba and Afro-Cuban practices such as Santería and Palo Monte. Shrines to La Virgen de la Caridad del Cobre, Cuba’s patron saint, coexist with offerings to the orishas in private homes. Religion here is not hidden—it is expressed in music, art, and community ritual. The batá drums of Santería echo through neighborhoods, and churches continue to draw vibrant congregations. Spiritual life endures as a defining force of Cuban identity, as vital as art or politics. From Wifredo Lam, whose surrealism drew deeply on Afro-Cuban spirituality, to his close friend Picasso, with whom he shared such a symbiotic exchange of ideas that critics still debate where one influence ends and the other begins. Even in Picasso’s later work, one can trace echoes of Lam’s visual language, proof of a dialogue that placed Cuban modernism at the center of twentieth-century art. From Lam and Picasso to today’s painters, performers, and photographers, Cuban art has always been both mirror and dialogue.Oscar’s Odyssey journeys often include studio visits, gallery talks, and private performances, because it is in these intimate settings that the heartbeat of the island is most clearly felt.
Nowhere is Cuba’s story written more visibly than in its architecture. Old Havana, a UNESCO World Heritage Site, preserves the colonial imagination with plazas, fortresses, and cobbled streets that still carry the echoes of empire and trade. Moving outward, Vedado reveals the ambitions of the 20th century—an eclectic mix where aristocratic mansions stand beside grand hotels and soaring modernist towers, still the epicenter of Havana’s civic and cultural life. Further afield, the quieter districts add new dimensions: the republican harmony of Santos Suárez, where neoclassical and art deco homes survive with surprising integrity; the broad boulevards of Nuevo Vedado, where tropical modernism found its most consistent expression; and the former Country Club, once the “Beverly Hills of Havana,” whose golf course and clubhouse were transformed in the 1960s into the daring National Art Schools. Seen together, these neighborhoods do not form a catalog but a continuum—a living testament to aspiration, reinvention, and cultural will. And yet Cuba cannot be contained by Havana alone. The island unfolds across valleys and wetlands, ports and provincial capitals, each with its own voice. Sometimes journeys move west toward fertile farmlands and tobacco fields, other times south to coastal towns of colonial grace, and still farther east to cities where music and resistance have their own cadence. I have led groups through places asfamiliar as Trinidad and Cienfuegos, and as far-reaching as Santiago or Baracoa. But these are only glimpses. The truth is that Cuba cannot be reduced to a single itinerary—it is a country of inexhaustible stories, each journey an introduction to something greater. Cuba’s politics are inseparable from its culture. To travel here is to encounter questions of ideology, faith, and belonging. What makes the journey remarkable is how these questions emerge in daily encounters: a farmer in the countryside, a guide at a historic site, an artist in a small studio, or a family opening their home for dinner. Such encounters show that Cuba is not a monolith but a dialogue of many voices. This is why Support for the Cuban People travel is not just a legal framework—it is a philosophy.
With years of experience in curating specialized journeys, Oscar’s Odyssey is not a newcomer. We have guided lawyers, art collectors, universities, cultural institutions, curious individuals, and families seeking to reconnect with their heritage or introduce younger generations to their past. Each journey is tailor-made, built on research, relationships, and a deep respect for local voices. What distinguishes us is the commitment to substance. We do not offer packaged tours. We offer experiences rooted in context: a performance explained by the artist, a walk through a neighborhood that reveals both history and aspiration, a site framed not only by the past but by the questions it raises for today. This blog will reflect that same commitment—less a bulletin of departures, more a conversation about the ideas, the people, and the encounters that make travel matter.
Travel to Cuba is not always simple. Flights change, infrastructure challenges persist. But it is precisely this complexity that makes the journey worthwhile. To travel here is to engage, to listen, to observe, and to contribute meaningfully. Oscar’s Odyssey exists to guide travelers through this process—not just logistically, but thoughtfully. The restrictions do not diminish the experience; they enrich it, ensuring that travel is about genuine human connection. This is only the first chapter, and Cuba is a book that refuses to end. Each journey reveals new voices, new streets, new horizons. What seemed complete opens into another story, another perspective, another unfinished thread. This journal is the beginning of that unfolding.We will return with new entries at their own rhythm—different places, different voices, the same inexhaustible island. Each post will be a fragment of a greater whole, a story that resists conclusion—because Cuba itself never concludes.
So return with us. Read, and then read again. The next chapter is already waiting.
