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The Havana Wind

  • Author:
    Dan Gerber
  • Published:
    Winter 2017

When I was growing up on the eastern shore of Lake Michigan, there were hot summer days, given to mirage, when I thought I could make out the skyline of Milwaukee across the lake, 90 miles away. I probably just wanted a glimpse of something exotic, and for years wondered what a “Milwaukee” might look like.

Now I live in Key West, and there are nights when Havana, about as far away as Milwaukee is from Michigan, seems to shimmer in the moonless dark. You cannot see Cuba from Key West, of course, but it’s always just over the horizon, enchanting yet remotely menacing. The one solemn note struck on the Conch Train, a trolley tour of the island, comes when it pauses at the “Southernmost Point in the Continental U.S.” and the driver announces, “Ninety miles over the water there lies communist Cuba.” People often squint, as if trying to catch a glimpse of a great shark cruising the edge of a reef.

Fifty-six years ago, Cuba was a weekend getaway for wealthy Americans, who would fly down to Havana, and for not-so-wealthy Key Westers, who would take the family fishing boat across the Florida Straits. They went for the slightly illicit taste of gambling in the casinos or the aura of Latin debauchery. Then revolution, the Bay of Pigs, the Cuban Missile Crisis, the specter of communism, and two generations of isolation transformed the once-beautiful playground into the darkly shrouded satellite of the Evil Empire. And in 1961, the U.S. government, bowing to pressure from the Cuban American exile community and to a residual vendetta against Castro and communism in general, imposed a trade embargo against the island. It became off-limits to American companies, including airlines, so the best way to get there directly was by boat.

My friend A.D. Tinkham, a Key West artist, and his wife, Rebecca, own a 38-foot trimaran, Restless Native, and they often invite my wife, Debbie, and me along for sunset cruises. Debbie and I are experienced sailors, and A.D. and Rebecca enjoy the company of people who appreciate the workings of the boat as a break from their usual business of ferrying snorkelers and sightseers out of the reefs that surround the lower Keys.

It was on an evening junket in the summer of 1994 that the idea of sailing to Havana came up. What if, rather than turning back at sunset, as was our routine, we just kept going? There is nothing illegal about Americans going to Cuba, and therefore nothing for which we could be prosecuted—unless it was proved that we had spent money there. True, the government—specifically U.S. Customs—frowns on the idea of American citizens traveling to Cuba, but investigating every vessel headed south from Florida would be akin to the state highway patrol pulling over every car traveling 66 mph. As for the Cuban government, it welcomes visitors from Europe, even depends on them to sustain the tenuous economy. We didn’t see any reason it wouldn’t welcome Americans as well.

We knew of a dozen boats that had made the crossing in the past year, and, to our knowledge, none of their crews had been blown out of the water or thrown in jail. The only troubling incident had occurred last April, when John J. Young, the leader of Basta!, a movement dedicated to running supplies to Cuba, had been detained by U.S. Customs officials on his return to Key West from Havana. Agents had roughly searched his 44-foot fishing boat and confiscated two bottles of rum, eight Cohiba cigars and two T-shirts. The search had won the government a good deal of adverse publicity of the “jack-booted thug” variety. We discounted the incident as a strictly political statement and set about planning our trip.

A.D., hoping to play according to Hoyle, inquired at the Customs office in Key West about forms and procedures. “I can clear you for Mexico or the Bahamas, but I can’t clear you for Cuba,” an agent warned him. “If you go there in a commercial vessel, it could be impounded.” Then, with a wry smile, he added, “But I didn’t ask you the name of your boat.” A.D., whose boat is commercially registered, beat a hasty retreat.

Setting sail

We persevered of the next six months, discussing our plans with friends, some of whom had made the trip themselves. I was given the name of a man who had made several crossings, and I called to ask his advice. He was away, but the message on his answering machine was encouraging: “If you are thinking of going to Cuba, go. It’s a beautiful country.”

So at 4:30 on a clear May afternoon, after freeing up our schedules for a three-night journey, packing a few extra provisions and goodwill trade goods—soap, toothpaste, aspirin, Miami Dolphins and Grateful Dead T-shirts, and a few baseball caps from the Saltwater Angler, a friend’s fly-fishing shop in Key West—we set out.

As we left the harbor, someone radioed to ask where we were going.

“Oh, just down to Women Key,” A.D. replied, referring to a remote island 10 miles to the west.

“I heard a rumor you might be headed somewhere a bit south of that,” the radio voice rejoined.

“No. We’re just headed out toward Woman,” A.D. dissembled.

He wasn’t lying, exactly. Owing to the strong southeasterly flow of the Gulf Stream—65 miles wide and two-and-a-half knots, according to the last report we had gotten from NOAA Weather Radio—we had decided to tack west toward Woman Key and sail 25 miles past it until we paralleled the Marquesas, a group of islands near the entrance to the Gulf of Mexico. There we would catch the Gulf Stream, the warm ocean current that flows around the tip of Florida and north along the east coast, and let it carry us toward Havana.

It was a beautiful evening with a fair breeze from the west. We were in high spirits as we passed the last navigational buoy at the end of Southwest Channel. Our home island was fading, and as the last trace of the outlying Keys dissolved into a chain of broken dots, the adventure became real for us. After a year of talking about it, our next landfall was actually going to be Cuba.

An hour beyond the channel, we passed a dead sea turtle—a large hawksbill, bloated and floating to our port side. At first I had taken it for a truck tire, though as we drew close, its tautly swollen skin glowed like burnished copper in the last red rays of the sun. “Not a very good start,” said Rebecca. And for the next hour, nobody had much to say.

At eight o’clock we approached the Western Dry Rocks, nine miles from Key West. Heading southwest, we bisected the cobalt-colored Gulf Stream. I could feel its pulls on the tiller like a sudden shift in the wind.

The Florida Strait is the main shipping route to the Panama Canal for vessels from Europe and the East Coast of North America. It’s a bog water, and a busy one for cargo carriers ten thousand times Restless Native’s tonnage. One of these seaborne warehouses could unwittingly crush us like flotsam under its bow, so it was important to keep a close watch for silhouettes on the horizon and to closely track the progress of navigation lights during the night.

Around 9:30 we met the track of the Gypsum Baron, a mega-freighter we had spotted an hour earlier off our stern quarter. It looked as if we would cross her bow, but then she adjusted her course to the south, and as we saw her transom off toward Galveston, her shudder wake crashed over our bow and put us in a confused, deck-sopping sea.

When we had regained our composure and changed into dry clothes, Rebecca fixed supper, which we capped off with tumblers of Haitian rum. As the moon rose, chasing away all but the brightest stars, the wind fell off to the point that we dropped our jib and fired up the diesel.

A close call

A.D. and I were sleeping below when the first call came from the Coast Guard. Debbie was at the helm, and Rebecca came down to wake us. It was 4:30 a.m., and we emerged like hibernating groundhogs.

“This is the United States Coast Guard calling the vessel four miles off our port bow at twenty-three degrees, twenty-three minutes north latitude and eighty-two degrees, eighteen minutes west longitude.”

After a moment, I said, “Maybe they’re calling someone else,” and we decided not to respond, even though we could see the cutter’s lights to the northeast. By their fourth call, we had booted up a handheld global positioning system and confirmed that they had us pinpointed.

A.D. responded, “Coast Guard, this is Restless Native.”

“What is your last port and intended destination?”

“Tell ’em the truth,” I said. “What else can we do?”

A.D. shrugged and said, “Restless Native out of Key West and bound for Marina Hemingway.” I held my breath, waiting for the ax to fall.

“What is the purpose of your trip?”


They asked for our vessel numbers, boat length and the number of people aboard, then told us to stand by. It was a long few minutes, protracted by a silent litany of imagined repercussions, before the voice returned.

“Have a safe trip.”

We celebrated with a predawn sip of rum. We were making six knots to the southwest, compensating for the eastward pull of the Stream. At about 10:30, 18 hours after we had left Key West, we began to wonder if we had gone too far west and missed Cuba. Then, suddenly, there was Havana, materializing through a blanket of heavy smog. Our arrival was heralded by a few dozen flying fish, at least 10 inches long, the largest I had ever seen. We entered Marina Hemingway, the yacht basin just west of the city, through a narrow break in the reef a quarter-mile offshore.

In the outer harbor, we spotted the Cuban flag flying outside a small stucco building: Cuban Customs. We tied up along its pier. For three hours, we visited with uniformed officials from Agriculture, Immigration, Customs and the Cuban Coast Guard. The protocol was the same with each: handshakes, soft drinks or coffee, forms to fill out.

They spoke little or no English, and our collective Spanish was rudimentary at best. We consulted our English/Spanish dictionary frequently and used some creative sign language. The officials were friendly and welcoming. One, dressed in uniform and epaulets, left the boat wearing a Saltwater Angler hat.

We had landed during the annual Hemingway Sport Fishing Tournament. Dozens of fishing boats were lined up at the piers, along with sailboats from Sweden, Brazil, Germany, Britain and France.

At the concierge desk of a hotel near the marina, we booked rooms for the night at the Inglaterra Hotel in Havana, made dinner reservations and arranged for a car with an English-speaking driver to pick us up the next day. Then we called a taxi and headed into town.

’Muy interesante’

The streets of Havana seemed oddly familiar, like cities in Florida I had visited as a child. Traffic was light, and almost all of the cars were pre-1958. We entered on Fifth Avenue, a broad thoroughfare of palatial homes—Havana’s Sunset Boulevard—that had, since the revolution, become the embassy row.

We arrived at the Inglaterra Hotel around 7:30. It had jury-rigged partitions for walls, and exposed wiring. From our balcony, Debbie and I heard a political rally going on in a baroque building across the narrow street. We couldn’t pick up many of the words, but the tone of the rhetoric and the martial music of the brass band were unmistakable.

The plumbing in our room was out of order, as was the telephone, so I went down to the front desk to see when we might be able to shower. On my way back up, I met a man at the door of the elevator and, after we played a little “after you, Alphonse” about who might enter first, he smiled at me and said, “My Ingles is not so good.”

“Nor is my Spanish.”

“You are Inglés?” he asked.

“No. Americano.”

He pulled in his chin, widened his eyes and, with a tone of incredulity, asked, “Norte Americano?”

“Sí.” I nodded.

“Norte Americano?” He smiled and shook his head slightly. “Muy interesante,” he said, and we bowed to each other before he got out on his floor.

The next morning the four of us wandered a bit through the streets of Havana, which were, by the turn of a corner, elegant or squalid, friendly or forbidding, redolent of diesel fumes or gardenias or human waste. The Cubans we encountered seemed surprised that we were Americans rather than Europeans. They said they were happier learning English than they had been struggling with Russian. We handed out goodwill items and were given one- and five-peso notes as gifts. Cuban money seems to be purely decorative: All the prices in the bars and shops were in American dollars. We paid for everything in cash, to avoid leaving a paper trail.

After lunch we met our driver, Umberto, who took us into the countryside. We drove past sugarcane fields, muddy streams and forests, and often encountered horse- and ox-drawn carts. As it turned out, Umberto spoke no English, but he suffered our poor Spanish and drove us past his mother’s house and the houses of several friends, pointing first out the window, then to himself, saying, “Mi amigo, mi amigo.”

Hoping to return to Key West early the next day, we decided to sleep on the boat. At five o’clock, we asked Umberto to drop us off at Marina Hemingway. After a drink at the Old Man and the Sea Hotel, we turned in.

What appeared to be apartment buildings were being built near the marina. As we were preparing for our departure the next morning, one of the construction workers wandered over. After standing and watching for a few minutes from the dock and making several attempts to help, he asked if we would take him back to Key West with us. He said he had friends in Miami with “mucho dinero.” We shook our heads and told him we were sorry. A few minutes later we were relieved we had.

At the Customs dock on our way out, a Cuban Coast Guard officer gave our boat a meticulous search, looking under every cushion and in every tiny drawer, presumably searching for stowaways. We had nothing Cuban aboard, not even a cigar.

‘Go on home’

We cleared the harbor on a brisk east wind. Heading northeast, we had the Gulf Stream working for us most of the way and made the crossing in 13 hours. Except for a whale that rolled and spouted a few dozen times off to port, we had an uneventful trip. An hour out of Key West Harbor, I radioed U.S. Customs and, with some trepidation, announced, “This is Restless Native, inbound to Key West from Marina Hemingway.”

The woman who responded seemed taken aback. “Marina Hemingway? That’s in Cuba, isn’t it?”

“Yes, it is,” I replied.

“Hold on a minute.”

A few seconds later a man’s voice joined hers on the line, and she said, “There’s a boat out there that says it’s coming in from Cuba. What am I gonna do about that?”
“It’s pretty late,” he said. “Why don’t you just tell them to hit the dock and go on home.”
My guess is that they figured anyone ingenuous enough to announce they were sailing in from Cuba was unlikely to be a smuggler.

We arrived in Key West after midnight, a bit weary, and addled by what had seemed like an odyssey in time. We were happy we had made the crossing while Cuba is still what it is, while it still has some grit. A few years down the road, I suspect, it may be a port of call for the Love Boat, as homogenized as Key West and all the other formerly distinctive island cultures in the aquatic theme park that once was the Caribbean.?