Philosophy & Approach

At Oscar’s Odyssey, travel is never just about seeing new places—it’s about entering into dialogue with them. I believe a journey should move beyond itineraries and landscapes to reveal the stories, people, and forces that shape a culture.

My philosophy is rooted in three simple ideas:

1. Travel as Cultural Exchange
I see every journey as a two-way street. Travelers come to discover Cuba, but in the process, they contribute to it—supporting local artists, entrepreneurs, scholars, and families who are the island’s living heartbeat.

2. Depth Over Display
I avoid packaged tourism and surface-level sightseeing. Instead, I design experiences that connect you with context: an artist explaining their work, a historian guiding you through a neighborhood, a family opening their home. It’s these encounters that bring meaning, not just memories.

3. Embracing Contradiction
Cuba is a land of paradox—scarcity and creativity, tradition and innovation, silence and expression. My approach is not to simplify these contradictions, but to honor them. I believe it is in complexity that the soul of a place is revealed.

Why It Matters:

Travel isn’t to collect destinations, but to cultivate understanding. Each journey is an invitation to engage with culture, faith, and history in ways that leave both traveler and host changed for the better.

Oscar’s Odyssey exists to guide travelers through this process with care, respect, and intellectual curiosity—so that every trip becomes more than movement from place to place. It becomes part of a larger story: one of connection, discovery, and meaning.