The Impossible Dream: Racing to Cuba

For the crew of Impossible Dream – including 3 wheelchair-bound sailors – and the organizers of the Conch Republic Cup, the question was the same: Can they pull off the regatta from Key West to Cuba?
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In a day race off Havana during the Conch Republic Cup, Harry Horgan eyes the competition as the 60-foot cat Impossible Dream sails by the famous El Morro Castle. Herb McCormick

Questions, questions, questions. For the crew of the catamaran Impossible Dream — including three wheelchair-bound sailors — and the organizers of the resurrected Conch Republic Cup, the primary query was one and the same: Was there any chance of pulling off last winter’s revamped regatta from Key West to Cuba? After all, despite a recent thaw in diplomatic relations, the last CRC, in 2003, had concluded with armed federal agents arresting one of the organizers in her home, at dawn, in her nightgown. And with wild weather delaying the start, would the competitors in the fleet of 54 boats be up to the challenge of tackling the stormy Florida Straits? As it turned out, the answer to all these concerns was ultimately revealed on a hand-painted Cuban mural quoting none other than Raúl Castro: “Sí Se Puede.” The translation: “Yes You Can.”

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Impossible Dream is one cool carbon cat. Herb McCormick

Fits and Starts

In the hazy late afternoon of January 29, off the salty islands of southern Florida, the starting gun fired — precisely 24 hours after it was originally scheduled to — and following a 13-year hiatus, the eighth edition of the Conch Republic Cup, from Key West to Cuba, was underway. Of the 50-odd boats and nearly 500 competitors on the starting line, the only yacht helmed by a sailor in a wheelchair — and a slightly nervous one at that — was our 60-foot carbon catamaran, Impossible Dream. Moments earlier, from behind the wheel of the inside steering station, Deborah Mellen had hailed the race committee to check in on the VHF. “That was a first,” she said, and then wondered aloud to ID‘s raffish skipper, Capt. Will Rey, if she should relinquish the helm.

“No way,” said Capt. Will. “You’re driving for the start. That’s the spirit of what we’re trying to accomplish here.”


Then, like Dennis Conner at the start of an America’s Cup race, she positively nailed it, and, perhaps fittingly — she’d basically and generously bankrolled the purchase of the boat — was nearly overcome with emotion. “I’m getting weepy,” she said. “Thank you, everybody. What an experience. Thank you.”

Over the radio, the principal race officer bid the fleet fair sailing in the “historic, pioneering” event. Gazing at our crew, which in addition to Mellen included another pair of intrepid sailors in wheelchairs, Harry Horgan and David McCauley, my only thought was, “Brother, you ain’t kidding.” And so began a remarkable journey with, for us, multiple story lines.

The first, of course, was the voyage itself, to the formerly forbidden land of cigars, rum and, you know, commies. The second was the reinstated Conch Republic Cup, a regatta with an intriguing, colorful history. Finally, there was the tale of Impossible Dream, originally designed and built in England for a paraplegic sailor felled by a skiing accident who wished to continue adventuring, and now the flagship of Shake-A-Leg Miami, an organization devoted to helping disabled people become more independent, vital and active, primarily by getting them out on the water.


The inaugural order of business, naturally, was the regatta’s first of three legs, a roughly 90-mile passage from Key West to the rather scrubbed and glitzy, by Cuban standards, port of Varadero. (From Varadero there would be another 80-mile race to Havana, and then a final 90-miler back to Key West — a triangle course — with the offshore segments sandwiched by some inshore buoy racing at the host ports; hence the event’s secondary title, Key West Cuba Race Week.)

At the outset, at least, getting started proved to be anything but straightforward; in fact, the hardest part of leaving Key West was, well, leaving Key West. An hour or two before the originally scheduled starting time on the afternoon of January 28, the race committee postponed festivities for an entire day when a string of nasty thunderstorms came roaring in from the south. There was some initial grumbling from the racers, but that dissipated when the thunder, lightning and 50-knot winds lashed through the Keys. Surely the race committee had made the correct call, but the postponement, and subsequent weather drama in the days ahead, would be a recurring theme that wreaked havoc on the scheduling.

But that was all in the future, and once we were finally underway, our first overnight leg was conducted in champagne sailing conditions. Along with the trio from Shake-A-Leg and Capt. Will, our team consisted of Harry’s wife, Susie; Lee Oldak, an experienced sailor from New York looking for a ride, who joined our crew at the last instant; and me, a longtime pal of Harry’s from our shared hometown of Newport, Rhode Island. Mere moments after our start, we set our big spinnaker and quiet, mild-mannered Lee became a whirling, kite-trimming dervish: “More pressure coming! Come up! Take that puff down! Now come up! Too high, too high! OK, nice.”


However, the 12-knot northerly at the start eventually backed to the east, and we sailed the entire leg on port tack, nice as could be, making a top speed of 13 knots. Sweet. Just before dawn, at the finish line, we eked ahead of When and If, the gorgeous 63-foot Alden schooner, a stirring sight silhouetted before a pastel sky, once owned by General George S. Patton. There was but one problem, and it was a relatively small one: Standing on the foredeck, we took stock of one another’s wardrobe of watch caps, fleece and multiple layers of foulies, and someone said, “Wow, we’re in Cuba, and we’re dressed for New England.”

But Capt. Will, always a voice of reason, had a different take: “Somewhere there’s a beach chair under a coconut tree with my name on it.” Then he went to find it.

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Capt. Will prepares to hoist our host’s flag. Herb McCormick

Little Orlando

Soon after tying up at Varadero’s Marina Gaviota (the official who greeted us – “Welcome to Cuba!” – wore a crisp white lab coat as starched, pressed and pristine as the fresh, spotless docks and the high-rise hotel and condos surrounding them), another visitor happened by. It was Peter Goldsmith, the event’s co-founder, who’d raced down on another yacht; he was there to collect his sea bag, as Capt. Will had graciously offered to carry some bags down for competitors on smaller boats with minimal storage.


Fittingly, the inaugural leg we’d just finished, the Michele Geslin Memorial Cup, was so named for Goldsmith’s wife and (wink, wink) “partner in crime,” who’d also been a race founder and who passed away several years ago. Despite his New England roots, with his lazy drawl and kicked-back demeanor, Goldsmith looked and sounded like a Key West native, though he’d been there “only” 33 years.

“Conch Republic Cup” is the perfect name for a regatta born and bred in wild Key West. As legend has it, the Conch Republic was so named in April of 1982, when then-mayor of Key West Dennis Wardlow “seceded” from the United States to protest a U.S. Border Patrol blockade that essentially shut off the Keys from the mainland to prevent illegal aliens and drug runners from rolling up the coast. Wardlow supposedly threw a stale loaf of Cuban bread at a hapless agent, declared war, surrendered, and later sued for reparations, all of which has forever endeared him to the locals, aka “conchs.”

Goldsmith said he started the CRC as revenge after the Key West Sailing Club “snookered” him into becoming fleet captain in 1996; the first iteration of the new event (there had been a couple of Key West-Varadero races in the 1970s) drew 40 boats. For the next seven years, as the race ran annually, Goldsmith received regular letters from the Office of Foreign Assets Control of the U.S. Treasury Department with a large red cease-and-desist order across the top. He did neither.

By 2003, though, OFAC had had enough. A posse of agents “with guns on their hips” rolled into the pre-race briefing and party and made a speech detailing why nobody could go to Cuba. This advice was roundly ignored, and everyone set sail anyway. But when they returned, the OFAC men boarded their boats and confiscated cameras and GPS units. The next day, they arrested Goldsmith and Geslin at their home and hauled them to Miami to face federal charges of trading with the enemy. The judge almost immediately dismissed those charges, but the point was made.

“We’d had our fun,” Goldsmith said. “Everybody liked the outlaw part of it. But I wasn’t going to rub their faces in it.” So that was that.

Until this year, that is. “I knew I was always going to do it again,” he said. “I was just waiting for the right moment.”

The stars began to align in May of 2015, when the organizers of the Havana Challenge, a race from Key West to Cuba on Hobie Cats, persuaded U.S. authorities to ease travel restrictions to run their event. By this point Goldsmith had lured his old sailing pal Jeff Drechsler to come in as regatta chairman for a new CRC, and the organizational wheels really began to turn. Any potential roadblocks were then demolished several months later, when OFAC historically authorized travel to Cuba under a dozen “general licenses,” including “athletic competition” and “support for the Cuban people.” Since Goldsmith and Drechsler hoped to get Cuban sailors involved, the CRC ticked a couple of boxes.

“We didn’t even need to go through the process of applying for a separate OFAC license or anything,” said Drechsler. The CRC would no longer be just a regatta, but “a cultural exchange through sport.” All systems were go.

All that said, there wasn’t much culture being exchanged inside the metal gates of Marina Gaviota in Varadero. On ID we took to calling the place Little Orlando for countless reasons, the most obvious being that it reminded us all of Disney World. With its gleaming docks (but only a handful of visiting cruising boats, from France and Canada), multiple restaurants and pools, spas, private beach, golf course, and so forth, it was pretty clear that if you didn’t wander past the gates and the guards and spent your entire vacation in the marina, you could easily imagine you’d never left a Florida theme park. It seemed like Marina Gaviota (officially owned by “the army” and unofficially by Raúl Castro) was built for the throngs of U.S. tourists who will soon invade its shores.

We did take a wander past the guardhouse, hiring a vintage ’52 Plymouth for a look around touristy Varadero and its working-class suburb, Santa Marta, the backstreets of which actually felt and sounded like the Cuba we’d expected to find. We even stopped at a great Cuban steakhouse next to an oil derrick with the message from Raúl, “Sí Se Puede,” painted on its fence, and we took it as an omen. We were all dying to get to Havana. It seemed Raúl had granted us permission.

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Once Marina Hemingway reopened, Capt. Will guided the 60-foot cat through the narrow channel and into open waters. Herb McCormick

Westward Ho

Motoring to the starting line on February 1 for the Cuba Coastal Challenge, the second CRC distance race, an 80-miler along the island’s northern shoreline from Varadero to Havana, Capt. Will wet his finger, pointed it to the sky, and said, “There’s not enough air to fill the spinnaker.” Once again, he was right.

The proceedings got underway at 1100 in about 5 knots of easterly breeze that slowly built throughout the day, and soon enough our kite was indeed set and drawing. Up on the horizon, the well-sailed Antrim 52 cat Little Wing, our main competitor in the multihull class, slowly began to pull away and show us her transom, just as she’d done on the initial leg from Key West. It was déjà vu all over again.

Harry and David, both excellent helmsmen, did much of our driving. Harry is an experienced, accomplished sailor, but this was all pretty new to David, an extremely cool cat who runs an art gallery in South Beach, and who’d become a quadriplegic several years ago after a diving accident in a swimming pool. (“Nothing good ever happens after midnight,” he explained.) This was certainly an adventure for all of us, but perhaps even more so for David. Locked behind the wheel for hours on end, with razor-sharp focus, he kept the chute filled and the boat moving well in the truly tricky breeze, which would have been a challenge for even a pro sailor. Before all was said and done, we would sail several hundred miles, but that particular spell when David was on the helm was my favorite stretch of the entire trip. The dude was a natural.

With the questionable pleasures of Varadero in the rearview mirror, we settled into the sail westward. Slowly but surely, it became kind of magnificent. Ahead and behind, colorful spinnakers dotted the horizon, but the coast itself was the star of the show. The green, lush, low rolling hills were accented by occasional headlands and bluffs and even a long bridge spanning a deep valley. There were no road signs whatsoever, but every so often we’d see a lighthouse, highway or small settlement.

As we closed on Havana, well after sunset, the distant glow gradually became defined lights that morphed into a big city skyline full of high-rises and blinking taillights moving up and down the coastal highway that lines the famous promenade called the Malecón. In the wee hours, under a beautiful, starry sky, we identified the committee boat, crossed the finish line and, per their instructions, started to follow a Jet Ski into Marina Hemingway. The organizers had had their hands full sorting out details in Varadero (it’s hard to score a yacht race with digital software when you can barely get on the Internet), so it seemed fitting when the Jet Ski sputtered, coughed and ran out of gas. So, yeah, welcome to Havana. It was only the first of many surprises.

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Before sailing for Key West, the author (foreground) posed with the Impossible Dream team: (back row) Susie Horgan, Jorge Gutierrez, Capt. Will Rey and Lee Oldak; (middle row) David McCauley, Deborah Mellen and Harry Horgan. Herb McCormick

Holy Havana

Once we’d cleared customs and tied up in Marina Hemingway, the first order of business was unloading the 43-inch flat-screen TV we’d carried down for Jorge Gutierrez, a Cuban-American and Shake-A-Leg’s fleet facilities manager back in Miami. It had spent the previous two weeks stashed in a big North Sails bag in Capt. Will’s berth, and as it was hauled ashore, he said, “Well, there goes my girlfriend,” none too wistfully.

Jorge had flown ahead to make arrangements for our stay and had been invaluable in helping us sort out the maze of Cuban exchange rates, arranging transportation, and finding nice, extremely affordable accommodations ($40 a night, including a large, delicious breakfast) with friends who owned a bed-and-breakfast in Havana for several of our crew, including me, who’d decided to stay in the city. He also invited us to a huge pig roast at his family’s lovely home in the suburbs, easily our best night in Cuba. On a related note, it seemed folks with relatives in Florida, who could send cash home, lived quite comfortably in Havana. (When I asked a friend of Jorge’s how people got by, he said, “Western Union.”)

Havana itself, however, was easily the most confounding place I’ve ever visited. The music, cigars and vintage cars were all, of course, as bewitching and entertaining as advertised. And it’s surely unlike any modern metropolitan city in that there are no billboards (except for the occasional revolutionary slogan, that is), McDonald’s, Starbucks or anything else of that ilk. Nobody walks around glued to a cellphone, texting madly. (That might be because the Internet is severely regulated, available only via a $2-an-hour card you purchase in a bodega to access Wi-Fi in select public parks.) All that is probably the most civilized part of being “uncivilized.”

The people, too, are unflaggingly friendly and curious about American visitors. And much of the architecture is mind-blowingly beautiful, intricate and spellbinding. “Look at that middle piece,” said a friend from another raceboat, taking in a stone arch carved into a downtown apartment house. “It’s like a piece of jewelry.”

But you don’t have to wander far off the beaten path to find neighborhoods and infrastructure that are nothing less than an unmitigated disaster, a massive, crumbling wreck after decades of decay, neglect and disrepair. Much of it resembles pictures of London after the blitzkrieg. It’s astonishing. Naturally, like every tourist, I wandered into the Museum of the Revolution, the temple to Fidel and Che, where you can read reams of propaganda about “lackey” Americans and the fool Batista, who bent to the imperialists’ demands and earned his just deserts. But there I was also amazed to find a bust of Abraham Lincoln, a fellow champion of the oppressed. And you’re never far in the city from one of the watering holes once frequented by Ernest Hemingway, yet another Yank who remains universally revered. Conflicted: That’s how I felt after a stroll through Havana.

In addition to sightseeing, we actually had a regatta-related mission in Havana: competing in the Castle de Morro Cup, a day race off the Malecón. We’d skipped the buoy race in Varadero (with full wheelchair access, an electric furling mainsail, and a hydraulic mainsheet and traveler, ID is built for voyaging, not banging around the cans), but that wasn’t really an option in Havana.

Every U.S.-Cuba regatta — and they are growing almost daily — has an important common denominator: Commodore José Miguel Díaz Escrich, of Marina Hemingway, who sorts out the necessary permits and licenses with the Cuban government, hosts them all. It’s politically imperative for Escrich to show the visiting yachts galloping off the Malecón in the heart of the city, and as Capt. Will noted, our fishing gear and barbecue were on station and ready for duty.

“We’re in full racing mode,” he said.

There was just one hitch. As we prepared to leave the marina, a fresh-faced Cuban customs official appeared alongside and summoned Jorge, who had the permit to race with us and was excited to do so, and began questioning him intensely. It became pretty clear he wasn’t going anywhere, and before Capt. Will and Deborah could protest, he just shrugged his shoulders and waved us off. Even though racing in his home waters would have been a lifelong memory, it wasn’t worth compromising his visa for a day of sailing. So much for the cultural exchange through sport.

Somehow I found myself at the wheel for the start, and I managed a fairly decent one. There’d been a war of attrition in the multihull class: nine at the start in Key West, four for the leg from Varadero, and now two for the Havana day race. Our old friends on Little Wing were once again our sparring partners, and we had good speed on them for the first couple of miles, though with their centerboards they held quite an advantage, as they could point much higher. Couple that with a boneheaded tactical error on my behalf (I tacked inshore instead of riding the better breeze outside), and that was that: a bridesmaid again. But the ID crew was psyched anyway. For several of them, it had been their first buoy race ever.

Due to yet another impending cold front bearing down on the island, to beat the weather, the ever-challenged race committee rolled the finish of the day race into the start of the leg back to Key West. But we weren’t quite ready to head home, so instead we returned to Marina Hemingway. For ID, the CRC racing days were over.

So, unsurprisingly, back at the docks we broke out the libations. It turned into a fine party. Deborah reckoned we deserved some regatta silverware, so somebody turned the stainless-steel platter on which a hot pizza had been delivered into a trophy that was fitting for our second overall in the multihull class. We were actually pretty proud of our accomplishment, but the prize still seemed appropriate.

After a while we were joined by a Cuban skipper who lives in Miami but travels back and forth and keeps his racing sloop in Marina Hemingway. We’d all had a few by then, and the festivities had gathered steam, but his poignant, sobering thoughts put pretty much everything into perspective. They require no explanation:

“I have a dream, a dream to sail my own boat to Key West, to sail where I want. But that is not possible. You have a boat, the Impossible Dream, and you have made your dream possible. You have sailed to Cuba. So maybe I will change the name of my boat. Maybe I will call it Someday.” Brother and comrade of the seas: yes, hopefully, someday. In the meantime: God bless America.

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Stormy waters along the Malecón lining Havana Harbor delayed Impossible Dream‘s departure from Havana. Herb McCormick

Home Sweet Home

Ultimately, as it turned out, leaving Cuba was even more difficult than departing Key West had been. As forecast, the cold northerly filled in hard. First the Malecón, swept by breaking seas, was closed, followed by Marina Hemingway itself: Nobody could come or go. “Better to lose a minute of your life,” said the harbormaster, “than to lose your life in a minute.” The message was somewhat cryptic, but we got the idea. With Marina Hemingway shut down on a Friday evening, the place lit up. Someone had described the architecture as “early gulag,” which seemed especially appropriate as scores of extremely inebriated Russian tourists started stumbling and mumbling about. A pig was roasted on an open spit, and the disco pounded into the wee hours. It was a long night.

It all made antsy Capt. Will even more fidgety than usual, and when the harbormaster opened things back up early on the morning of February 6, we were almost immediately out of there. With aplomb, the skipper maneuvered ID through the tight channel, lined by breakers on each side, and into open water. We were headed home.

Whether it was the rather vicious seaway and boisterous Gulf Stream, coupled with a double-digit northerly, that left a few crew a bit queasy, or the fact that we were all trying to digest what we’d just experienced, ID was a quiet boat on the trip back. There was plenty of time for contemplation.

Yes, we’d all felt fortunate to scratch the curious itch nearly all American sailors have about Cuba. And on the one hand, we’d all loved the Cuban people, the cold mojitos and fresh cigars, the amazing sights. But it quickly becomes difficult to enjoy all the sensual pleasures while watching people get constantly hassled, who are hungry and standing in bread lines. After a while it sucks the fun away, and you kind of feel like an entitled jerk. That was the intersection at which I’d arrived. I was quite happy to be headed north.

From the Cubans themselves, I heard from more than one person that the country is headed in a new direction: “The young people, they will change it. They don’t care about the revolution.” And why would they? Like Raúl and Fidel, the revolution is old. Done. Over. That’s the problem with Cuba. Half the folks are looking forward. The other half are looking back. Everyone is betwixt and between.

And one more thing. These days, everybody says: “You need to go to Cuba. Now! It’s on the verge of monumental change!” Well, I’m here to tell you, until the Castro boys croak, and for a good while thereafter, nothing will happen quickly in Cuba. Hell, it’ll take decades before the toppling buildings will even begin to be renovated. Everything is too ingrained, too incestuous. So take your time. Trust me. There’s no huge rush whatsoever. A dozen hours after we set sail, after an extremely bouncy ride — and a wondrous adventure with now-treasured friends — the lights of the Conch Republic finally flickered ahead. They could not possibly have been prettier.

For More Information

The next Conch Republic Cup will be based at Key West’s Stock Island Marina Village and is scheduled for January 25-February 4, 2017. For complete details, visit the event website

For more on sailing and chartering opportunities aboard the catamaran Impossible Dream, visit its website,

Herb McCormick is Cruising World’s executive editor.