Tour guides develop a preference for certain destinations. As a local tour guide, with 20 years in the making, I have one: The eastern region of Cuba.

The trio that was entertaining us at “La Ferminia” restaurant got emotional when a member of our tour stood up, walked to where they were and handed over a bag containing guitar strings. “This, said the lead singer, is more important than the tip we could get from this whole month”…

Santiago de Cuba, located along Cuba’s Southeastern coast, is a vibrant port city rich in Afro-Caribbean culture and revolutionary history. Known as the birthplace of the Cuban Revolution, Santiago offers a unique blend of traditions and influences, with a scenic backdrop of the Sierra Maestra mountains and the Caribbean Sea. This city, home to over half a million people, is a must-visit for travelers looking to explore Cuba’s past, present, and diverse cultural heritage. Next year, Cross Cultural Journeys will offer trips to Santiago, including visits to historic sites like the Moncada Barracks and immersive experiences with the local community.

Since 1998, Cross Cultural Journeys has offered in depth cultural experiences in Cuba. During this time we have built meaningful relationships with local organizations, NGOs (non-governmental organizations) artists, musicians, entrepreneurs, doctors, architects and everyday citizens. This is what makes our journeys there so special.The arrests picked up both sides, and some even non-violent protesters will face as much as one year in prison…

Over three years ago, my son was performing in an all-nation orchestra in Orlando, Florida, over Thanksgiving break. I had been to Cuba in 2011 with the Washington State Bar Association and thought, as long as I was going to Orlando, I might as well investigate how easy it would be to take my son to Cuba for a short trip. I contacted Cross Cultural Journeys, a Bainbridge Island tour company specializing in trips to Cuba. That conversation led to plans to take the high school jazz band to Cuba in April 2020, with fundraisers and lots of planning. Unfortunately, Covid canceled our trip.

Jazz master Roger Glenn shares his deep connection to Cuba, its music, and its people ahead of an intimate journey to the Havana Jazz Festival. In this conversation, Glenn reflects on his past trips, the rich history of Afro-Cuban jazz, and what travelers can expect from this immersive experience. From legendary music venues to cultural insights, Glenn offers a glimpse into the rhythms and stories that make Cuba a jazz lover’s dream.