Do they check your boat when you go back to America?”
“They do,” I said, though I had no idea if anyone did. “And I think the Cuban customs officials bring dogs on board, before we leave, to make sure no one is hiding on the boat.” I didn’t know this either. It was something in a cruising guide I’d read—probably out of date.
It was late. We were standing under a dim, yellow streetlamp at Marina Hemingway, where Lost Boys, the 42-foot Endeavour I’d sailed from Sarasota, Fla., was spending its last night in Cuba before sailing back home. The boat was squared away. Only the goodbyes were left.
Julio, a 28-year-old father of two, leaned against the hood of his car, a tired, blue Lada idling diesel exhaust into the hot night. He pointed toward Lost Boys and the dark sea and sky beyond.
“I can swim. I’ll meet you off the coast.”
I pretended I didn’t understand. In 10 years of cruising, calling on ports with living conditions far worse than those in Havana, no one had ever asked if they could stow away on my boat. I put my hands in my pockets. I didn’t know how to respond.
“You can pick me up in the water, and when you get to Cayo Hueso, you can just leave me near the beach. I can swim from there.”
I felt a tightness in my throat. I couldn’t tell if it was desperation or simply a desire for a better life that drove my new friend to want to take such a risk. I supposed it was a little of both.
I tried to tell him how things were changing in Cuba. I explained that a young man like him, full of energy and ambition, would surely find success as the Cuban economy improved. I believed it.
Julio had been our man in Havana. He and his partner, Enrique, cheerfully drove us around the old city, slipping us in the back door at the Buena Vista Social Club, dropping us at El Morro just after sunset to hear the canons fire, laughing aloud when I mentioned that the Russian Embassy resembled a giant watchman.
“It’s not so easy in America,” I told him. “We have plenty of problems, too.”
He looked offended, like I’d mistaken him for a child who knew nothing of the Shangri La that lies across the Florida Straits. “Oh, no. I need to get to America,” he said. “If I can get to America, I know I will make some good.”
There were no dogs at customs. Just two bored soldiers, kids from Vinales in rumpled fatigues. When Lost Boys cleared the sea buoy, I looked back toward the marina and thought I spotted Julio’s blue Lada parked near the marina breakwater. I imagined him and Enrique leaning against the car’s front bumper with the sun on their backs, two young Cubans staring across the Gulf Stream toward their magical America.
I pointed the bow north and switched on the autopilot. In an hour, the only sign of Cuba was gray smoke from an oil refinery. A brisk easterly filled the main. It was still early, and the distance we had to sail wasn’t so far. I realized that if Lost Boys could keep up this speed, we might catch a glimpse of Cayo Hueso before dark.
About halfway across the Strait, in the middle of the Gulf Stream, my eyes began to play tricks. The sea reflected an impossible blue as if in competition with the sky, and no matter how much I squinted, I could find no line between the two. When I finally discovered the horizon, broken by the fuzzy shape of a distant ship, I was struck by the notion that of all the reasons to sail, the wonder that it works on perspective is the one I cherish most.