
3. Push Boundaries… safely
Like many young Black men who grew up listening to hip-hop, I had fantasies about visiting the roughest parts of Los Angeles. When the time finally came, I didn’t just stay in Beverly Hills or Santa Monica. I went to Compton, Long Beach, and tracked down a popular taco truck in South Central. And yes, it was rough. But it was also real, and it completely changed the way I consumed West Coast hip-hop.
The same thing happened in Cuba. Our resort was located in the dreamlike city of Varadero, but it quickly became apparent that there was a truer version of the island we weren’t being shown. After a short conversation in Spanish with a security guard and a quiet exchange of currency, a guide took us on a road trip through the countryside. He showed us Cuba from the perspective of the locals. The conversations we had still influence how I live and love today.
Travel is about landscapes. Transformation is about people.
Yes, you’ll remember the mountains, temples, and lakes, but what lingers longest are the faces—the shopkeeper who tells you about his family, the woman who teaches you how to make tortillas, the stranger who points you toward a hidden trail.
Don’t gamble with safety, but don’t cage yourself off either. Take the martial arts class. Join the walking tour. Accept the invitation to a community event beyond the tourist areas. Travel isn’t about observing life from a distance. It’s about being woven into it, if only for a moment.
