Cuba or bust

If I have any goals in this life, I have trip goals. Epic motorcycle camping trip across Canada. Epic train journey from Paris to Tehran. Epic bush plane exploration of Africa. (Notice a theme here?) Sailing to Cuba was high on this list.

We caught wind of the Miami to Havana sailing race while reading online about the new law allowing boaters’ access to Cuba (Thanks President Obama!). Of course, American sailors have been sneaking into Cuba for decades. Cuban customs’ officials helpfully stamp Visas, leaving American passports innocently blank. But it never hurts to be able to do things aboveboard. So we signed up, and got down to business—any epic journey comes with an equally epic stack of paperwork and red tape. Let’s just say I drank a lot of prosecco while filling out and re-filling out various forms.

By mid-January, we had our nine-person crew assembled and flights were booked. It was really happening! Now for insurance…securing this turned out to be a Herculean task. No insurance company wants to insure a boat in Cuban waters. Most of the 46 boats in our regatta ended up sailing without any insurance, but this was not an option for us. There was also the story, fresh in our minds, of the 90 foot power boat that cruised to Cuba without insurance, got into trouble while in Cuban waters (losing three of four engines), then high-tailed it back to international water where it promptly sank. Whoops. Not a good day, and not one that we could recover from, so insurance it was. When the budget version didn’t come through, we finally hit “send” on what I’ll call the ‘platinum plan’ just before we lost cell service off the coast of Florida.

We were sailing down as part of the inaugural Miami to Havana Regatta, put on by the Coral Reef Yacht Club in Miami. It was the first race from Miami to Havana in over 50 years. When President Obama opened up diplomatic relations in late 2014, boat travel was approved so long as the sailors involved were part of an officially organized travel experience involving the Cuban people. The way the race committee handled this caveat was by planning a second, shorter, race once we arrived in Havana. This second race was to go along the Malecon, the huge seawall that stretches along the Havana waterfront. The idea, ironically, was to have Cuban citizens aboard the sailboats during this race. A fantastic idea in theory, Cubans are not even allowed to step foot on private boats.* (thank you, wet foot dry foot policy). While not an official law, any recreational boating activity by Cubans is prohibited by the Naval Command Center, and this commission has the final word on all things Cuban and boats, so there is no higher authority one can appeal to. Yay, Communism. To put it another way-There wasn’t a chance in hell any Cuban citizens were going to be allowed aboard a fleet of American boats, sailing along the waterfront, gleefully waving goodbye.

The starting line off the Miami coast was the usual exciting traffic jam of sailboats jockeying for position, support boats yelling their goodbyes and photographer boats taking pictures. The excitement was short-lived, as we turned towards Cuba and away from the wind. Robin Hood is a 55,000-pound beauty of a vessel. A Ted Hood-designed Little Harbor, she is made to go fast enough while being so heavy that she is very sea-worthy–and comfortable. (She had a sister ship also entered in the race, and rumor has it their captain wanted to forgo cockpit cushions in order to shave a few pounds off. We got more than a few good laughs out of that story as we trailed farther and farther behind them all the way to Havana.) With a tailwind and no spinnaker, we were traveling at Robin Hood’s worst point of sail…meaning, very slowly. The official race distance was 210 nautical miles and we traveled roughly 262 miles, thanks to a whole lot of jibing. But hey—we were going to Cuba. We popped some champagne, made some lasagna, and got ready for what we assumed (you know what they say about that) was our only night of sailing.

Welp…40 hours later in the pre-dawn deep blue light following our second night at sea, we started to see more and more tiny fishing pangas checking what seemed to be small traps. Most of these boats had little or no lights so we would come upon them in the dark like phantoms, that became more and more real until suddenly we were looming right over them, and could faintly make out the brief waves of the fishermen working aboard.

Pulling into Ernest Hemingway Marina, 42 hours after the excitement of the starting gun, we were in for our first surprise–it was all easy. Navigationally, entering Havana’s port was a breeze. Customs was equally simple. We were warned of Cuban officials checking crew members’ temperatures and vital signs for evidence of illness, and checking every inch of the boat for signs of…well for who knows what. Checking, checking, searching, and checking some more…this we were warned of time and again. Instead, they sat down, had a coke, and looked at a few forms. Then they shook our hands and were on their way. And we were on our way to find cabs, which turned out to be pristine 1950s convertibles, one with a belly-dancing driver named Billy who took us to his favorite restaurant. Was it a scam? Did we get a bit taken advantage of? Of course!!! And the food was delicious, the view was unreal, the mojitos were tops, and it was all worth it.

Dinner that night was in a gorgeous crumbling mansion with a rooftop bar that looked out over the lights–and dark holes–of Havana. The meal was fresh ceviche and ropa vieja, fish tacos and pulled pork sliders. It was the most delicious food we had ever eaten. The walls were crumbling around us but the decor and food was five-star. This was Havana, in all its old glory, current circumstance, and hope. While walking around during our second, and final, full day in Havana, we all remarked on how clean the city was. Even when the sweeping views included the gorgeously renovated Grand Theater of Havana, home of the National Ballet, mixed with crumbling buildings being swallowed whole by vines, the overall picture was a clean one. Many boulevards were swarming construction zones and yet they were still just so clean. This is one feature I’ve noticed in other poor countries. People are willing to take any job, and many unemployed will walk around with trash barrels cleaning up for a pittance. Whether the poor financial scenario or Communism is to blame, it made for some beautiful vistas. That said, we did have one underage cabbie who drove us the “back way”, presumably to avoid the cops, then promptly got pulled over and arrested, leaving us to walk through some neighborhoods that seemed to live under piles of trash, with even dead dogs left baking in the ditches. As with any perception, there is more than one way to look at it. The fact that the tourist areas are clean do not erase the reality that most Cubans live with when they return home at night.

During our visit in mid-February, Pope Francis made a brief appearance at Jose Marti International Airport, and as I write this on March 20th, President Obama and his family are touching down in Air Force One for a historic visit to Cuba—the first by a sitting U.S. President in over 80 years. Just after landing, Obama tweeted “Que Bola, Cuba? Just touched down here, looking forward to meeting and hearing directly from the Cuban people.” Anthony Bourdain went to Cuba during his most recent TV season, and he asked the Cuban club owners he met what they were going to do once the flood of American tourists, and money, started. They laughed nervously, and just kept shaking their heads–after half a century of being in the dark, it is likely hard for them to imagine a flood of any kind of money or (good) attention. I’m just so glad we got to experience it before the floodgates open and American tourists pour in. It was truly a 1950s film set, seemingly frozen in time and beauty. I’m sure many Cubans have a less rosy opinion of their 1950’s facade, but to a visitor it is beautiful, and if nothing else it is fascinating to see.

We planned a party cruise home–24 hours of rose champagne, Ed jamming on the ukulele, and maybe some trolling for bonita. Instead of cruising right into the Gulf Stream as planned and having it shoot us straight to Miami (the best laid plans…) we saw 30 knots of wind right on our nose and 10-15 foot seas. No one had a drink. No one had anything but a stray saltine cracker or two as we heaved and pitched our way home. Miami was quickly abandoned in favor of the much closer and more direct Key West. Not far from my mind throughout this trip were the thousands of dilapidated rafts that Cubans risk their lives on just to reach Florida. In those conditions it was unfathomable, and yet hundreds of thousands have done just that in the decades since Cuba closed its borders against any exodus.

When we got in to Key West around midnight, we pulled into the first slip we could see, and abandoned ship for showers and margaritas. After all the checklists I had gone over for returning to US waters and clearing the way with the USCG, US Customs and Immigration, in the end we had to call them five times and finally took a cab there at lunchtime the following day to have them check out our passports. Apparently they prefer to board your vessel as soon as it enters US waters (a truly laughable idea given the weather), but no one we talked to seemed terribly concerned. We could have smuggled 40 Cubans out with us had we felt so inclined and they could have strolled right off the dock into a new life in the Conch Republic. As it was, we hadn’t returned with so much as a single Cuban cigar. The experience alone was enough.
Follow the adventures of SV Robin Hood on Instagram @boatsboardsandbabies


*There are loopholes in the no-boating policy but it takes a foreign spouse and an absurd amount of paperwork and jumping through hoops. I am not 100% positive that no Cubans participated in the race, but we did not see any on any of the other boats, and I imagine that it didn’t happen



8 thoughts on “Cuba or bust

  1. Very well written!! Sorry I had to miss this trip. Though not envious of the return, I’ve eaten my share of saltines 😉 Cuba is now high up on my list of places to see. — When I’ve traveled to poor countries, I haven’t seen that same thing with the trash. Just had to learn to coexist with it. — Did you interact with any locals not in the taxi or service industry, and what was that like? — Need captions on your photos. & you should submit this for publication, maybe salon, or matador, or Cruising Outpost (used to be Latts & Atts) 🙂

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