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JUNE, 1959—My college roommate and I are aboard a Lloyd Areo Colombiano DC-3 headed from Miami to Bogota, Colombia, a few thousand feet above what the airline ticket agent smilingly described as “the shark-filled waters of the Caribbean”.
Gradually an island appears below: a big island, green and mountainous. Cuba. Down there lives Ernest Hemingway, the hero of every aspiring writer of the day. And in the States we are hearing a lot about a new government there headed by a man named Fidel Castro. “I will go there some day,” I promise myself.

More than four decades passed, and the politics of an American going to embargoed Cuba became as daunting as the shark-filled waters. But after three years of planning and preparation I am on my 32-foot sloop Dream Weaver headed from Key West to Havana as the first light of a new day spreads across the choppy, ink-blue Gulf Stream. My crew member, John, was a sailing friend recruited at the last minute for a sail to a place where few Americans dare to venture.
Sailing to Cuba is discouraged by the US government—to put it mildly. Your boat can be boarded and seized and you can be fined six figures. Among the documents on board is a license from the US Treasury Department allowing me, as a freelance journalist, to visit the forbidden island just 90 miles away. My mission was to track down Hemingway locations in Cuba and see for myself what was there today. My guidebook was Hemingway in Cuba by Cuban journalist Norberto Fuentes, first published in Spanish in 1984.

Although traveling to Cuba is illegal for most people, it is easy for sailors to acquire essential planning information. On board we carried Nigel Calder’s very detailed Cuba: A Cruising Guide, Christopher Baker’s excellent Moon Handbook Cuba, and paper charts. Our Cuban courtesy flag came from Bluewater Books and Charts in Ft. Lauderdale, FL, which also carries chart kits of Cuba, thanks to Nigel Calder’s mapping efforts as he circumnavigated the island. From Calder’s book, we had entered into our GPS the location of the buoy off the entrance to Marina Hemingway: N 23?05.4 W 82?30.6.

We had been nervous for days as the boat was hauled for repairs at Peninsular Marine on Stock Island near Key West. Dream Weaver was showing some wear and tear after the first part of this voyage, the 2,000 miles from my home in Burlington, Vermont, just 45 miles from the Canadian border. I had been traveling south for almost five months, and now the challenges of the final short leg to Cuba were directly ahead.

First, there was the Gulf Stream. Sailors don’t cross when the wind is out of the north and butting heads with the north-flowing Gulf Stream, kicking up square waves sometimes called “elephants”. Harry Morgan, the doomed smuggler in Hemingway’s To Have and Have Not said it well. “Brother, don’t let anybody tell you there isn’t plenty of water between Havana and Key West.” But overnight the wind had clocked from north to southeast and our weather window was open.

Second, we didn’t know what to expect from the Cubans. Our government had embargoed Cuba for half a century and seemed determined to meddle in Cuban internal affairs. Hot rhetoric flew back and forth over the Straits of Florida, but was this government posturing or real people talking? My third concern was the impact the embargo was having on us. Dream Weaver was going uninsured because nobody would insure a boat going to Cuba. We were taking American dollars in denominations of $20 or less, but if the boat broke or something else came up, we were stuck. We would have no access to money in our American bank accounts; no credit cards would work. The embargo is all about preventing US dollars from finding their way into Cuban hands. And if we did have trouble, there is no US embassy. We might or might not get any help from the US Special Interests Section.

As we loaded the boat for departure the word had spread along the dock that we were pushing off for Marina Hemingway. One local skipper came by with a package containing over-the-counter medicines, personal care products and a baseball cap. It was for one of the boat boys at the marina. “He has a sick kid…some kind of allergies and can’t sleep at night. Would you take it with you? I’ll show you what it is…nothing illegal.” We stashed it in the hanging locker with a bundle of similar products we were bringing…shampoo, aspirin, pencils, medicines, and baseballs.

Another local sailor docked just ahead of us. “See you there in a couple of days.
The Cubans are great, man, friendly, generous. If they have something they’ll share it with you. They expect you to do the same, so don’t be surprised if they ask you for something. But they love life, they love to dance, they love their families…very strong families. If you have good Spanish you can practically be one of the family.”

These Key West guys made it sound like going back and forth to an embargoed Cuba was just another routine cruise. It was 2 p.m. and time to push off for a mid-day arrival in Havana.We pointed Dream Weaver west for five hours s part of our plan to play the current in the Gulf Stream, then at Cosgrove Shoal turned due south toward Havana and the sea buoy off Marina Hemingway. As darkness closed in John made one of the wry comments that qualifies him as a good shipmate for an adventure: “You know, of course, when you sail into the Gulf Stream you immediately go to the bottom of the food chain.”

Through the night, freighters and cruise ships decked out like Christmas trees came and went across our horizon, and I plotted our position on the chart every two hours to see if the current of the Gulf Stream was sweeping us off course. At 9:30 a.m. a tanker with a tall conning tower passed across our bow. When it was appearing over the horizon, it looked like an apartment building. Twenty minutes later I saw one, two, three apartment buildings in the distant sea mist. Then I realized they really were apartment buildings: it was the skyline of Havana. Cuba. It had taken decades, but we were almost there. I grinned at John. “so far so good.”

The sea buoy appeared exactly where it was supposed to be, and as we spotted it we had our first taste of the Cuban experience. A small power boat was headed for us at high speed and although we expected a boatload of guys in military fatigues with rifles, it passed us pulling four water skiers who pointed at the American flag flying from our stern and waved a friendly greeting.

Although it took about two hours, the officials who cleared us through customs were polite, friendly, had a sense of humor, and set the tone for what would develop into our deep affection for and appreciation of the Cuban people. We had set out cold Coca Cola and Chips Ahoy chocolate chip cookies for the officials as a friendly gesture. I had also developed a list that provided detailed boat information and a list of electronics and equipment we carried on board. We were not there to sell into a black market.

The doctor who had checked our toilet and medical facilities jumped aboard and directed Dream Weaver to a space along the wall of Channel 2, just a few yards from a big swimming pool and a cluster of condominiums. John and I picked up our visas at the marina office and began to explore, passing the pool full attractive young women from throughout Latin America.

Marina Hemingway was not some backwater boat dock, it was a community built around four narrow channels lined with boats from around the world. Cuba’s connection to Hemingway was reflected in the names: The Old Man and the Sea Hotel, Papa’s Nightclub, The Garden of Eden Hotel, and marina offices at Villa Paraiso. It also contained a half dozen restaurants, a supermarket, a chandlery that delivered essentials like beer and ice, a laundry, a cigar store and, of course, a T-shirt and music CD shop.

We paused to stock up on Havana Club rum and Romeo y Julieta cigars, then returned for a swim. Later, as we lounged in the cockpit with rum and cigars, a young Cuban came by for a chat and filled us in on his view of the local knowledge:

Best beers: Cristal and Buccaneer dark.
Best rum: Seven-year-old Havana Club, but if money was no object, 15-year-old Havana Club Gran Reserva.
Best place to buy cigars: House of Cigars in Old Havana, on Mercaderes Streeet between Obispo and Obrapia.
Best kept secret: the second-floor rum sampling room next door to Hemingway’s best-known Havana hangout, La Floridita restaurant at the top of Obispo Street.
Best Hemingway hangout: La Bodeguita del Medio, a watering hole with solid Cuban food located on narrow Calle Empedrado a half a block west of the cathedral of Havana.

John flew back the next day, and I was alone for a month to explore Havana and Hemingway’s hangouts, becoming a frequent passenger on the shuttle bus that ran from the Garden of Eden Hotel into Old Havana at the Castillo de la Real Fuerza, one of four historic forts built to guard Havana Harbor.

The first ride from the marina provided glimpses of Cuba that initiated a love affair. We passed the beautiful mansions of Miramar, many of them now foreign embassies. A few minutes later we were on the Malecon, the ocean on our left and the beautiful Spanish Colonial buildings on the right, some of them restored but some badly in need of repair. We were in traffic with many of the pre-1959 American cars that have become famous, mixed in with Mercedes and Mitsubishis and bright yellow egg-shaped taxis built on motor scooter platforms.

Our drop-off point was at the fort. Completed in 1582, it is near the foot of Obispo Street, a pedestrian only walkway that is at the heart of rectangle of Old Havana Hemingway hangouts.

At one corner of the rectangle is the former Club Nautico at the Harbor, now a snack bar. Hemingway kept his fishing boat, Pilar, here while staying in Havana. Another corner is La Floridita restaurant, the inventors of the daiquiri. The third corner is the Sevilla Hotel and nearby Sloppy Joes, which pre-dates the Key West saloon of the same name on Duval Street. Hemingway did some of his writing at the Sevilla, which also has a literary connection as a setting in Graham Greene’s Our Man in Havana. The rectangle closes at La Bodeguita del Medio, famous for its mojitos. In Hemingway’s day it was a favorite of writers and artists because the owner let them imbibe on credit. Now these places are part of the Hemingway Trail, an organized tour.

Obispo Street begins at a beautiful little square behind the fort and gently rises 10 short blocks to Central Park and the Capitol building, which is modeled on the US Capitol in Washington. It was my first walk in Old Havana, so it was necessary to explore the Ambos Mundos hotel where Hemingway stayed for $2 a night beginning in 1932 when he and fisherman/rum smuggler Joe Russell (Sloppy Joe) first ventured over to Havana from Key West to drink, fish and chase women.

It cost me $2 to visit room 511 where a pleasant woman named Esperanza Garcia explained the Hemingway history and memorabilia, right down to the old portable Royal typewriter on the table. I ventured up one floor to the roof garden, where an international crowd sipped cocktails under a shaded pavilion overlooking the harbor, as Hemingway had once done. Very civilized, I thought. It was this scene he described in one of his early articles on marlin fishing for Esquire magazine.

I headed up the street for La Floridita, following the writer’s well-trodden path. Late in the morning, after wrapping up a morning of writing in Room 511, a Hemingway still in his 30s would head up Obispo dressed in khaki shorts, a cotton shirt and moccasins. He would arrive around eleven, have a couple of daiquiris, leave at noon and return at five for more cocktails.

At the door of LaFloridita, a gray-haired doorman in a red tuxedo coat and black bow tie opened the door for me and I faced the huge mahagony bar. At the far left is bust of Hemingway on a wall decorated with old photos of the author, including one with Fidel Castro at fishing tournament. Below the bust is Hemingway’s corner seat, respectfully roped off. I took the seat next to it, ordered a daiquiri and began to scribble in my little notebook. Maybe a creative spirit still lingered here.

The day was fading as I followed my map to La Bodeguita del Medio and struck up a conversation with a young American couple who had somehow slipped into Cuba from Mexico. “I love Cuba,” the young woman said. It was almost dark as I headed back for the Plaza de Armes and the shuttle bus.

The days ahead would take me to Hemingway’s home, Finca Vigia, where he lived longer than anywhere else, to the fishing village of Cojimar, the setting for some of The Old Man and the Sea, and to places I did not yet understand. My concerns about how an American might be viewed in Cuba were quickly dispelled by encounters with Cubans who were always friendly, engaging and curious about an American sailor. Some gave me letters to mail to relatives in the US, or walked along to practice their English. Walking along Cuba Street to catch the bus the smell of cooking and the sound of salsa music tempted me to peek through a pair of green shutters in a building that likely dated back to the 1600s. A man and a woman were dancing in their kitchen. I thought of all the intense people I saw in the States driving their Mercedes, and wondered how many of them dance with each other before dinner.

At the plaza and shuttle stop, I settled onto a park bench near a street light and watched a group of boys laughing and teasing each other as they played a game of baseball using a stick and a rubber duck…a bathtub toy. No ball, no bat, just fun.

The American girl at the Bodeguita was right. You could learn to love this place. And, just as this adventure had begun years ago, I made more promises. Some Cuban kids were going to have baseballs. I would learn Cuban style salsa dancing, and dance before dinner. And some day I would return to Cuba. At this writing, the first two are taken care of, and the third will be very difficult…again.


Sailing around Cuba
 
Sailing around Cuba
Text by Dave Schaefer
Sailing to Hemingway’s Cuba
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