
Cuba is huge—it spans more than 600 miles from east to west. We saw abundant signs of civilization as we sailed along the coast and closed in on Havana after a six-and-a-half day passage from Fajardo, Puerto Rico. We dodged fish pots, usually laid out in strings of eight to 10; freighters came and went from the old port of Havana; an old military launch that looked definitively Soviet-era steamed past us to the north. But there was no sign of the marine police, the USCG or other authority figures. I was almost sure we’d be boarded once officially in Cuban waters, but it didn’t happen.
We docked at Marina Hemingway, which is like no other “marina” we’ve ever been to. It’s huge, and is laid out in four large east-west canals, each nearly a kilometer in length and about 75ft wide, with substantial land between them. Each “slip” is a designated spot alongside a dilapidated concrete bulkhead, with run-down hotels and abandoned or unfinished apartments backing the waterfront. It felt like a colorful, post-apocalyptic Ft. Lauderdale.
Customs was much more efficient than we’d expected, and the folks were as friendly as everyone said the Cuban people would be. Several groups of uniformed officers came by the boat to do various inspections, each of them polite and respectful, even taking off their heavy military-style boots as they boarded our Swan 48, Isbjorn. A comically small, fluffy dog was brought aboard to sniff for illicit cargo. I specifically requested to have my passport stamped, which got genuine smiles from the guys behind the desks, and we were ushered off the dock and directed to our “slip” within an hour of our arrival.

“Jose” met us at our slip, I recognized him as the same cheerful voice that had guided us through the cut just after dawn. It was the end of his overnight shift (the marina is staffed around the clock), and he joined the crew in Isbjorn’s traditional landfall champagne toast, despite the fact that it was only 0800. He even requested a refill! After that two of our crew immediately set out to look for some cold beer, ice and Havana Club rum, while my wife, Mia, and I cleaned up the boat and greeted the seemingly never-ending line of government officials who came to inspect everything from our toilets and trash to the vegetables we still had onboard.
Isabelle’s House
The next morning we left the boat for a big colonial house in Vedado, the Mafia-funded district just west of Habana Vieja (Old Havana), that we’d booked for the entire crew to stay ashore with a local family.
It’s impossible to overstate the chaos of the streets in and around Havana. First of all, the city is huge, with something like two million people living in the greater area. And thanks to all the old cars, the air pollution in and around the city is suffocating. It was hard to tell if the once-colorful architecture was simply faded by time and neglect or stained by lousy air.
In Vedado, enormous houses stood along wide tree-lined boulevards, neatly organized into square grids. The architecture, despite some neglect (though not as much as the media would have you believe), is incredible. Our place was on the second floor and had a balcony that fronted the main street. There were five bedrooms, each with intricate tile work on the floors and 15ft ceilings. Each morning Isabelle and her husband would prepare a breakfast feast for us—fresh papaya and bananas, hand-squeezed guava juice, cheese omelets, fresh-baked bread and pot after pot of deliciously strong Cuban coffee.
Habana Vieja & La Revolución
Mia and I followed the crew’s lead and made it a point to stick together for the most part. After seven days offshore together, we’d gotten quite fond of each other despite starting the trip as strangers. Each morning started with a rendezvous at the fabulous Hotel Nacional. Back in the 1940s this was the home of famous cabaret shows, housed a large casino and was the place to be for the celebrity class. When Castro, Che Guevara and the revolutionaries finally reached Havana in 1959, they repurposed the Nacional for the people. The grounds overlook the MalecÓn and oceanfront to the north. Several huge cannon point toward the United States and tunnels were dug beneath the hotel at the height of the Cuban Missile Crisis. This was practically Ground Zero during those frightening days, and the hotel was as much a fortress then as it was a place for guests to stay.
The lobby would become the crew’s meeting point each day we spent in Havana, largely because you could also exchange currency there. Cash is king in Cuba—the country employs two currencies, the CUC or “Convertible Peso” that tourists use, and the CUP or “Cuban Peso” that is reserved for the locals—and besides the banks, the big hotels are the only places to get it.
We made it our mission on the second day to check out the Museum of the Revolution and Old Havana. The museum used to be the Presidential Palace when General Batista ruled the land. After the revolution the place was given back to the people (kind of). You can still see the bullet holes along the marble staircase on the interior from a failed assassination attempt on Batista.
The Cuban government portrays its version of its long history with the United States quite differently from what is taught in school back home. The displays were reminiscent of a high-school history project put together by a group of enthusiastic students with scissors and construction paper, and they were insightful and a wonderful way of seeing world events in a different light. The United States is still very much the “bad guy” in the eyes of the Cuban government, as evidenced recently by Fidel’s scathing letter following President Obama’s historic visit.
On the bottom floor, we found a large mural depicting the “Ring of Cretins”—full-body caricatures of Batista, Ronald Reagan (dressed like a cowboy), Bush Sr. and Bush Jr. (the latter dressed in a Nazi uniform) with plaques next to each describing how they wanted to spoil the revolution.
Later, we strolled around Habana Vieja’s maze of streets looking for signs of Hemingway’s hangouts. We quickly found one of his favorites, La Floridita, the writer’s “local” bar and legendary home of the original Daiquiri. It has become one of the biggest tourist traps in the city and is no longer a place to go for a drink and a chat, as Hemingway so often did. There is a bronze statue of Papa himself at the end of the bar that patrons take turns posing beside for pictures. That said, it doesn’t take much imagination to see the place as it was in the ‘30s and ‘40s, as all of the décor and architecture remains original and highly authentic.

The French Place
On our last day in Havana, Mia and I completed our rum and cigar mission, returning yet again to the Hotel Nacional to buy the real stuff. In Cuba, cigars, rum and coffee are prized and sold only in official government stores. You can buy it all on the streets, but it’s probably counterfeit (particularly the cigars). Currently, Americans are allowed $100 each of a combination of rum and cigars and $400 total of items purchased in Cuba for personal use back home. Since a basic bottle of Havana Club rum costs roughly $7, this amounted to a lot of stock our crew of six could legally bring home.
We met up with the crew later on and hopped into a 1957 Chevy Bel Air for the ride back to Vedado, where we had the best meal of the trip at a small French place. A locals’ restaurant, it was classy both inside and out, the food was top notch and it was cheap—$10 got you a full meal, cocktail and dessert included, with fresh bread to start and table-side entertainment.
The stories about Cuban music are all true. Every cafe, bar and restaurant we visited had local, live musicians providing the soundtrack to our food and drinks—everything from seven-piece Mariachi bands to my favorite, a duo at the French place. The woman played an extraordinary Latin guitar while the man effortlessly kept the beat on his maracas and sang with the voice of an opera singer. They wandered over to our table about halfway through the meal. The etiquette is to tip the entertainment if you’re satisfied—they’ll often play a few songs, then walk around the establishment with a hat to drop coins into—and we kept giving money to these two because they were so good. One of our crew, Greg, even got them to do a private little concert for his two young kids back home that he got on video.
Ninety Miles to Freedom
On departure day I had to find more cash to pay the marina, so Mia and Rob hiked down the road a piece to a tiny little bank where we exchanged the last of the U.S. dollars we’d brought along. The government, despite the rumors to the contrary, still charges a 10 percent tax on exchanging U.S. dollars (thanks to the embargo—it’s their way of penalizing us), so while the CUC is valued at 1-to-1 against the dollar, the best exchange rate you’ll find is $0.87—dollars go quick.
All the customs and marina fees are due at checkout. Rates at Marina Hemingway just increased this past April to $1 a foot, so we paid $48 per day for our stay. We didn’t use power, and water was charged at a minuscule rate, adding up to less than a $1. Customs fees, however, were more. They charged us a $55 cruising permit fee, and then each crew member was tagged with a $75 departure tax.

Nonetheless, it all went smoothly, if slowly, and we departed Cuba just before sunset after another precursory customs inspection to make sure we weren’t harboring any stowaways. The passage to Key West was comfortably uneventful—a warm 12-knot easterly propelled us north while the Gulf Stream gave us a nice boost in speed and curved our course enough to the east that we never had to tack or even sail close-hauled, despite the contrary wind direction. We arrived into Key West Bight Marina just after dawn, making the 100-mile passage in a little over 15 hours.
Customs at the small airport in Key West didn’t bat an eye when we said we’d returned from Cuba. Instead, they took our passports, the USCG license I’d gotten previously, disappeared for five minutes and returned all smiles, thanking us for coming and asking us to enjoy the afternoon.
For five full days, our senses had been overwhelmed by the sights, sounds, smells and craziness that is Havana. The city is everything you’ve ever read about, compounded several times over by the sheer size and complexity of it all, and the fact that you’re seeing it in Technicolor, in full-motion, in person. Our lingering impressions were of old Russian cars driving down the canal roads spewing black smoke; the crumbling concrete on the bulkhead that had me worried enough about the fenders to return to the boat, some nine miles from the city proper, on three occasions to check them; the first old American car we saw, a green 1950’s Buick convertible; the photos of Papa Hemingway fishing with Che Guevara and Fidel Castro hanging up in the Yacht Club bar; the horse-drawn carts clip-clopping down the main road outside the marina complex, followed by ’57 Chevy’s and Russian side-car motorcycles; real mojitos and the distinctive aroma of cigar smoke on every street corner, plus signs and symbols of the Revolution everywhere you look.
Havana is enormous and sprawling, thick with air pollution and traffic, and yet vivid with the colors of life. The internet is still banned in households (probably bad), so people interact with each other on the streets (probably good), making us feel like time travelers as much as travelers in the geographic sense. My phone was useless and gmail for business is still banned in Cuba, so I couldn’t check my e-mail.
I don’t think Americans will “ruin” Havana. The standard tourist traps are already there in many parts of Habana Vieja. And the city is so far from any widespread infrastructural improvements that any noticeable change there will be limited to some fancy hotels and restaurants that will inevitably pop up in the trendier areas. Greater Havana has a long way to go to fix up its side streets and back alleys. The sheer size of it means this is going to take a lot of time.
More importantly, it’s the people that make the case for visiting Cuba, in general, and Havana, in particular. Cubans are almost universally recognized as some of the nicest and most welcoming people in the world, and you have to give them the benefit of the doubt that this won’t change when the country opens up. Saying that opening up Cuba is going to “ruin” it is a direct insult to the people who make the place what it is. Beyond all the classic cars and crumbling architecture, it’s the people that both define the city and the country and make the place worth visiting.
For more images of this exciting excursion, click here.
Andy Schell and Mia Karlsson manage the Caribbean 1500 cruising rally, run training voyages on their Swan 48 Isbjorn, and have nearly 50,000 bluewater miles behind them
September 2016