Vamos a Cuba!

Join us as we try to hitch a ride to the island before the gold rush strikes.

Standing on the deck of the mighty vessel stood Papa Hemingway himself, pouring Silver Bullets into a humongous coffee mug and squinting out into the early afternoon. He said his name was Ed Gully and he was pissed he couldn't take me to Cuba.

"Another one of our freedoms gone down the tubes because of bullshit politicians," he muttered.

Gully had been part of a notorious 2003 race to the island that led to the ruination of a pair of local lives. "You go and see Michele Geslin," he advised.

Emily Flake
Emily Flake

Geslin and her husband, Peter Goldsmith, had become legendary on the island after federal agents dragged them out of their beds and indicted them on criminal charges for running a regatta between Key West and Cuba.

Since then, they moved their sail shop from downtown Key West up to Stock Island. So I abandoned Key West and made way for their shop. I arrived to discover a two-story warehouse. Its walls were lined with reams of colored synthetic materials. Breezes poured through cracked windows, and tunes sounded from a small radio.

"Michelle's not in," called a voice in a soft Southern-hippie drawl. "Why don't you sit a spell?"

John sat cross-legged and silver-haired on the floor, cutting material for a huge blue spinnaker. He said every two or three days someone eager to get to Cuba comes through the shop with a broken sail.

John retired about 10 years ago as an engineer at Ford. "Every industry I've worked in has been outsourced," he said, tossing the sail onto an old Singer sewing machine and stepping on the foot pedal. "Shit, all the materials you see on the wall are flown in from elsewhere. Boy, we buy everything from communist China. The only thing this country manufactures anymore is debt and bullshit."

The retiree still has friends — mostly Frenchmen and Canadians — who go to Cuba. "A 30-foot sailboat with a fiberglass hull is still pretty hard to pick up on radar," he said. "But if they put that eye in the sky on you, then you're fucked.

"If they want to get you," he added gravely, "they'll get you."

John doubted I'd get a ride. "It's like the Sixties around here, again, son," he laughed. "You don't know who's ridin' on your boat — you might be a damn government snitch for all I know."

He was interrupted by the arrival of Geslin. Standing a little more than five feet, snowy haired and clad in a red sweater, she looked like she could be featured smiling on a biscuit tin. She spoke sweetly and seemed to have come to a place where she could finally laugh about her ordeal.

But not too hard.

She and her husband had run a regatta to Cuba since 1996 as a fully funded group hosted by the Havana Yacht Club. The race took about a week, alternating between days of sailing and partying. The Cubans were even allowed to take their boats out past the border buoys and sail alongside the racers. Geslin made sure her hosts always won.

Upon their return from the 2003 race, their boats were searched by OFAC agents aided by dogs and local police. They confiscated maps, cameras, and trinkets. "Anything that looked like it had to do with Cuba," Geslin recalls. The following morning, armed officers dragged the couple out of bed (Geslin was in pajamas) and booked them on charges of conspiracy and trading with the enemy. In November 2004, a federal judge in Miami threw out the criminal case but didn't close the door on civil fines.

Indeed the Department of the Treasury has hounded them like a junkie relative.

"They wanted $11,000," Geslin said. "Then they wanted $6,000. I just got a letter last week demanding funds."

Geslin handed me a free T-shirt and gave me a hug goodbye. The blousy white tee read "Conch Republic Cup 2003" below an American sailboat drifting into the Hemingway Marina.

She couldn't help me get to Cuba.

After making a few phone calls to a couple of wayward Frenchmen, John threw his hands up as well. "People hate having someone along that doesn't know shit about sailing," he said.


All signs pointed to Stock Island's tragic shrimping community, a poor population locally associated with crack-smoking. No one really thought catching a ride with a shrimper would be a good idea, but time and money were running out. If they couldn't take me, no one could — and I would resign myself to living in Miami.

As I made my way past trailers and abandoned furniture, weird glares and long leers followed me down the road. A battered red Ford Escort veered onto the swale in front of me. The passenger side mirror had been smashed off, and the windshield wipers were broken.

A tire and a nurse's jacket occupied the back seat. A muscular 35-year-old man with odd scars on his cheeks sat drunk behind the wheel. His name was Joel, he wore nothing but blue swim trunks, and he told me to get in the car.

I climbed in and explained the Cuba plan. He flew into a tizzy.

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