My friend called. “I met this guy,” he said. “For a thousand dollars, he’ll get you a fake passport and visa to Cuba. What do you think?” I was all in. Fast forward to a runway that led to what looked like an outhouse where we filled out our customs forms. In Havana, we had no phones. We hid cash in our clothes. A few days into our trip we heard about the bar that invented mojitos.

We hired a driver who took us through dark, unlit streets. It was starting to feel ominous, especially when we pulled up to what looked like a stone quarry. I orchestrated a plan in my head—if things went south, hit the driver and run. Turns out the quarry led to a hidden bar, where a man in a tuxedo was mixing drinks. Even so, you always need a backup plan.