Explore Cuba with a Local Expert

Dear Adventurer,
It is with great pride and excitement that I invite you on an unforgettable journey to Cuba—my birthplace, my homeland, and the heart of a culture as rich and complex as its history. Born and raised on this vibrant island, I have witnessed firsthand the beauty, resilience, and spirit of the Cuban people. Our journey, Cuba: A Cultural Odyssey (with departures in December, January, and February) is more than a trip—it is an intimate exploration of a nation shaped by its past, energized by its present, and filled with hope for its future.
Cuba is a place of striking contrasts—where colonial and republican architecture stand beside revolutionary iconography, where the echoes of history blend seamlessly with the rhythms of son, rumba, and jazz, and where artistic expression flourishes despite political and economic uncertainty. It is a land where hardship has fueled creativity, where traditions have merged into something entirely unique, and where the past and present exist in a constant dialogue.
Our journey begins in Havana, where creativity and culture pulse through every street. We’ll admire the city’s incredibly diverse architecture, from grand colonial mansions to striking art deco, mid-century modern, and contemporary designs. We’ll walk through Havana’s historic plazas, experience its thriving arts scene, and enjoy a private jazz concert by the renowned Ernan Lopez-Nussa. A guided tour of the Museo de Bellas Artes, led by a contemporary art curator, will give us deeper insight into Cuba’s artistic evolution. In the following days, we’ll visit Ernest Hemingway’s former home, engage with artists and musicians at the Instituto Superior de Arte, and dance alongside professional Cuban dancers at La Casa del Son. Evenings will be filled with dining experiences at some of Havana’s most renowned paladares (restaurants in private homes), including La Guarida and El Cocinero.


Our adventure continues as we journey to Cienfuegos, where we’ll take a boat excursion in the Guanaroca Lagoon, home to flocks of pink flamingos. In Trinidad, a UNESCO World Heritage Site, we’ll step back in time as we wander its cobblestone streets, visit beautifully preserved historic homes, and enjoy live music in the town square. We’ll also experience Cuba’s natural beauty with a hike to a waterfall in Guanayara Park, followed by a relaxing afternoon at the Caribbean’s pristine Ancon Beach. On our final day, we’ll make a brief visit to Santa Clara to see the Che Guevara Mausoleum and Ernesto Guevara Sculptural Complex, a tribute to Cuba’s beloved revolutionary hero, before we head to the airport for departure.
I look forward to sharing this extraordinary journey with you!
Best regards,
Oscar Fernandez, Trip Leader
