I Sailed to Cuba to Castro's Funeral and This Is What Happened

Fidel Castro's remains travel across Cuba
••• Sven Creutzmann/Mambo Photo/Getty Images

The sun was barely up when I stepped out of the marina bathroom and overheard my neighbor, Aussie, speaking loudly as he shuffled containers around the back of his sailboat.

“Of course I’m going to go! This is a part of history!” I knew he could only be talking about one thing: Cuba.

“Are you sailing over today for Fidel’s funeral?” I asked Aussie.

“Yes. The weather looks great! Light winds from the east, it should be a perfect trip.”

“Can I come?” I asked, excited to have a real adventure to Cuba. I had lived in a sailboat in Key West for two years, but despite the recent ease on American tourism to the island, I had never sailed the 90 miles to Havana. My boat and my sailing experience are not ready for that journey alone.

The trip, of course, wasn’t without concerns. I was anxious about what the atmosphere would be like after the Cuban people lost their leader. The government had temporarily banned music and alcohol, and they were no doubt on high alert. The journey from Key West to Havana takes around 14 to 20 hours by sailboat.

Aussie rounded up a motley crew Key Westers: Franky, a fisherman who didn’t have any experience with sailboats; Wayne, who lived in the marina and was never sober; and Scott, a con artist who had been sneaking into Cuba for more than 20 years.

Scott was accompanying a mother and daughter who planned on booking through a certified tourism company with a luxurious catamaran, but the boats sold out. The two women looked apprehensive as the drunken, disheveled crew stacked fishing poles, boxes, and other items onto the no frills, “plan b” boat that Scott had arranged.

We left at sunset – much later than expected – with winds that were not a reasonable 9 to 11 miles per hour as Aussie predicted. Instead, they were blowing more than 25mph with waves around 12 feet.

“It’s a little sloppy out here! Pass me an orange juice!” Aussie shouted to Franky and Wayne, who had been drinking the entire afternoon. They rustled something up in the galley and handed a glass up the stairs to Aussie at the helm, his usual ripped tie dye t-shirt flapping in the wind. He spit the juice back out.

“Is there vodka in here? I said orange juice!” He passed the glass back down, but the galley crew looked confused.

“What’s wrong with it?” asked Wayne.

“I don’t know! Maybe it’s too strong? Add more orange juice,” Franky suggested not comprehending why the captain sent back a perfectly good ‘juice.’

“What is that beeping?” asked Martha, her Boston accent still present. A noise similar to a car’s seatbelt alarm kept going off every few minutes.

“Oh, it’s nothing,” Aussie assured her, and I heard her mumble something about the catamaran she could have taken.

 As we approached the notorious Gulf Stream, a powerful warm current of rough water, the weather continued to worsen. Items were falling down because the crew had been drinking instead of securing them. I tried to climb to the forward cabin when the television came crashing down on my shoulders. Franky was on the ladder when the boat pitched, tossing him into the wall. Wayne cut his hand on God knows what and it was bleeding everywhere. One toilet wasn’t functioning and the seat of the other flew off.

By this point, nearly all seven of us were heaving over the side of the boat, including Scott who had sailed to Cuba 200 times (or so he said).

Wayne, who was wearing my favorite sandals that had mysteriously gone missing from the marina a few days earlier, was chomping on a cigar and attempting to comfort Mindy, Martha’s quiet daughter, by telling her to look at the stars.

“Just reach up at the stars, grab them, and put them in your pocket,” he slurred. “Isn’t it beautiful?” He asked rubbing her shoulder.

“Please don’t touch me. I don’t feel well,” Mindy tried swatting him away.

“Hey captain, the engine is overheating,” Franky called. They turned it off, and the sound of the waves and wind howled louder. I curled up under the raincoat and attempted to sleep. I awoke with a sudden jolt as rogue waves splashed onto my body, completely soaking me as Captain Aussie shouted “this storm wasn’t in the forecast!”

“I’m going to pee my pants!” Martha wailed. “Do you have a bucket?”

“Go downstairs and use the head,” Aussie insisted.

“I can’t! It’s broken, and there’s boxes and fishing poles in the way.” Trying to pee in the toilet was like using the bathroom on an Amtrak train that had just derailed. We were all covered in bodily fluids.

“Hey captain,” Franky began again as the beeping noise went off yet again. “The water pump is broken. There’s water all over the floor down here.” Now everyone was scrambling.

The struggle continued overnight, and it felt like decades passed before the sun broke over the horizon, and Havana appeared on the skyline. The weather started to calm down as we arrived, broken and battered, to a somber nation in mourning.

Along the shores of Marina Hemingway, the Cuban customs agents waited, casually lounging in chairs under a shaded gazebo as we approached the silent city. Havana was the unlikely calm after our storm of Key West madness.

I clawed and crawled my way to the bow of the boat, my clothes crunchy and stiff from the saltwater soaks, but my socks and shoes were still soggy. My skin was sunburned from waking up outdoors and bruised from the television falling on me, and the smell of “adventure” (vomit) on my pant legs was wafting in the air. As I fought back the nausea, a massive, comfortable cruise ship coasted in front of us headed to Havana full of well-rested passengers.

After we settled in, our group visited Plaza de la Revolucion, where thousands gathered to pay their respects as monotone voices from loudspeakers praised Fidel’s accomplishments. Most were talking among themselves, sitting on the pavement in the square as if waiting for an outdoor movie to begin. There were long waits to hail Cuba’s old-fashioned Chevrolet taxis, and Havana was eerily quiet and calm.

“I think I’m having a culture shock,” said Mindy from Boston as we walked around Havana. “But not because of Cuba. The Cubans seem pretty normal. I’m having culture shock because of the crazy Key Westers and all their drama.”