From Chicago to Cuba: How a First Passport Stamp Became a Catalyst for Purpose

Earlier this fall, YourPassion1st partnered with Mi Casa Holiday to take a group of young adults on a 14-day mentoring experience across Cuba. This was a journey that marked many firsts. For most participants, it was their first time on a plane, their first time leaving the country, and for one, even their first time stepping beyond the boundaries of their own neighborhood.
Those “firsts” became the foundation for something bigger: confidence, curiosity, and a deeper sense of what is possible.

The Journey as the First Lesson
Before anyone stepped into Havana, growth was already happening. A night spent “camping” in the Miami airport, searching for power outlets, and bonding over a 2 a.m. Denny’s Grand Slam laid the groundwork for gratitude and camaraderie. Even in the exhaustion, our young adults discovered that opportunity often begins long before the destination in the patience, humor, and connection that travel demands.

Stepping Into a New World
Arriving in Havana opened every sense at once. The music, colors, heat, and energy instantly expanded our youth’s understanding of the world. A spontaneous moment at lunch, when Syar jumped on the congas and lit up the entire restaurant, set the tone for the trip: this would be a journey of expression, community, and stepping boldly into new experiences.
But the most moving early moment came during a music workshop, when Lia sang for the very first time. Her courage to take that chance reminded everyone that discovery happens when young people feel supported enough to push through fear.

Culture as a Classroom
Throughout the trip, Cuba served as a living classroom.
Our young adults learned by doing: cooking traditional meals with local chefs, exploring Old Havana, riding horses through Viñales Valley, and sitting in nature to reflect on mental health. They watched how Cuban artisans craft cigars, coffee, and pottery with patience and pride. They witnessed how creativity survives and thrives, even in communities with limited resources.These experiences did not just teach them about Cuba. They taught them about themselves, their resilience, their interests, and the value of slowing down to connect with others.

Service, Connection, and Giving Back
A major highlight of the trip was delivering donated hygiene supplies to families in need, thanks to our partners at BHealthCares and What About Us Inc. At the Quisicuaba Project, our youth saw firsthand how compassion transcends language. Simple items like toothpaste, razors, and shampoo carried enormous meaning. That day drove home a core truth: service is a universal language, and giving from the heart changes both sides.

A Deeper Understanding of History and Identity
Traveling south to Cienfuegos and Trinidad deepened the group’s understanding of Afro-Latino and Caribbean history. Visiting the Valley of the Sugar Mills, once a center of Cuba’s slave trade, was a powerful reminder of the creativity and resilience that grow out of struggle. Standing in a place so heavy with history brought new meaning to conversations about identity and legacy.

Living with local families in Trinidad added another layer of connection, showing our youth what it means to truly immerse in another culture. Home-cooked meals, late-night conversations, and daily routines became some of the most meaningful moments of the trip.

Rest, Reflection, and Leadership
After days full of learning and movement, the group slowed down in Varadero for a day of rest. Mindfulness came through laughter on the beach, floating in the pool, and simply taking time to breathe. Back in Havana, a leadership workshop tied everything together with a focus on empathy, resilience, emotional intelligence, and the courage it takes to pursue your passion.

A Celebration of Growth
On the final day, each young adult shared reflections and creative projects inspired by the trip. Their confidence, honesty, and clarity brought the entire journey full circle. A closing celebration with music, dancing, and community reminded everyone that Cuba was not just a destination. It was a launchpad.

Why This Trip Matters
YourPassion1st exists to help young adults overcome barriers, discover their passions, and find mentors who walk alongside them as they grow personally, professionally, and mentally. In communities where violence, trauma, and limited opportunity weigh heavily on young lives, exposure and mentorship can be life-changing.

This trip proved it.