It was a bit of an unexpected flashback. After all, it had been decades since I lived in the old Czechoslovakia (now the Czech Republic) and yet the feeling that bubbled up was the same. I stuck my camera out the bus window to capture yet another of a dozen billboards dotting the pockmarked highway that bisects Cuba. This one shouted “Por Siempre Fidel”—loosely meaning “Fidel Forever.” In keeping with the Soviet-style aesthetic, it had a star, although most others featured the leader’s profile or some muscular woman wielding a wrench.

I had waited a long time to visit Cuba, and chartering there just added to the allure. Flying in, I noticed unkempt fields and haphazard government-sponsored farms. (I didn’t realize it yet, but they were the harbingers of the provisioning woes to come.) A weird Big Brother vibe mixed with the laid-back friendly ease of the Caribbean, it was eerily similar yet completely different to the days of my childhood.

Our first evening in Havana set the tone—one that’s uniquely Cuban, teeming with activity, music and curiosity, especially about Americans. Our first stop was Floridita, a tourist bar where a bronze statue of Hemingway always has a fresh daiquiri placed on the bar, just waiting for the author to take a sip. Hemingway’s “favorite bar” is a great marketing tool throughout Cuba. Each has a fuzzy black-and-white photo of the man himself, sometimes accompanied by Castro, other times on his boat Pilar, ready to cast the hook.

As we strolled along the evening streets, two things became clear. First, there is no bad place to point the camera. The buildings and the people in Havana are as authentic as it gets, and everywhere there are street musicians and vegetable vendors. Second, there’s a feeling of security here. Maybe it’s due to the strict government control and the ever-present policia. Maybe it’s because Cubans seem to love Americans. Everywhere we went, people smiled, tried out their English and let us take their picture. Even the very serious-looking and well-armed Guarda Frontera officers relaxed once I learned the magic word when pointing to the camera—guapo—handsome.

We spent two days in Havana, which is about three too few. The grand old city is a mix of history, well-worn grandeur and the calamity of modern life. Private enterprise has gotten a foothold, judging by the numerous independent food kiosks, bed-and-breakfast accommodations (we stayed in an Airbnb) and, of course, those fabulous old Chevys, Buicks and Fords: all classics have been lovingly restored with sparse materials, which is why many are painted pink and most share the same seat vinyl. None run on their original engines since parts have long disappeared, and this necessitates a lot of time spent under the hood for their owners who all seem to be MacGyvers, able to fix anything with just about nothing.

Wine is scarce and sketchy, but the rum flows freely in Cuba, so we headed out for mojitos on the terrace of the famous Hotel Nacional: an establishment that stood watch over much of the activity of La Revolucion and still has the bullet holes to prove it. The relaxed ambience on the deck today hints at the days a half-century ago when celebrities and mafia dons strolled along the malecon below.

The next morning, a bus ride delivered us to Cienfuegos, a sunny resort town on the southern coast of Cuba. Also, there was the Dream Yacht Charter office, its docks were filled with catamarans behind an impressive, all-white yacht club, a remnant of the town’s previous splendor and prestige. Our provisions, including cases of mint to mix with our haul of Havana Club rum, were also all there, sitting on the seawall in the sun. However, there was a notable lack of produce, with the plentiful fruit and vegetables we had seen on Havana stands under the watchful eyes of both Fidel and the revered Che Guevara now missing. I remembered the woefully inefficient goods distribution system of the Eastern Bloc and sighed. I guessed (correctly) that snacks like potato chips, chocolate and nuts were going to be scarce as well.

Cienfuegos Bay is a large and deep harbor with one twisty outlet to the Caribbean. Since we had easterly winds of 25 knots, we opted to cruise west to the Canarreos Archipelago. Just before sundown, after a glorious 40-mile reach, we rounded the bottom of Cayo Guano Del Este and anchored for the night under its red-and-white rocket ship-like lighthouse. Along the way, we noticed waters marked off limits (presumably, Castro family fishing grounds) and the defunct Juragua nuclear power plant, abandoned after the Soviet Union collapsed and no longer supported Cuba’s economy.

The lighthouse keeper let us climb the steep steps for a majestic view—a few islands toward the setting sun, and just miles of water to windward. Regardless of which way you sail in these waters, east toward Jardines de la Reina (“Gardens of the Queen”) or west toward the Canarreos, the first day of charter is a long one in exposed waters with no bailout point. You must like to sail and have a good grasp on being offshore. The gardens are known for great coral and fine diving, while the western islands offer white sand beaches that are nearly deserted.

Just outside Cienfuegos Bay that first day, we secured a fish from a guy who was snorkel fishing and who we very nearly ran over as he was almost impossible to see in the chop—the first of many encounters we were to have with the Cuban fishermen who often live in the desolate out islands, taking their catch to a central place for shipping to the mainland. Most fishermen won’t take cash, as they’re not allowed to. Instead, the preferred currency is Havana Club, or beer at a pinch. Our meager rations were soon supplemented with fresh fish and crates of lobster, and since we had several pounds of butter, we ate well regardless of the initial provisioning. In return, we shared with locals our rice, pasta and sugar.

The rest of the week, the hops between the islands were much shorter. The sunsets were spectacular, the beaches (like Playa Sirena) pristine and the services non-existent. The Guarda doesn’t offer towing or any other kind of assistance, and there are no fuel docks, so Cuba’s coastline isn’t for the inexperienced, although it is ideal for those who want something off the beaten path.

Many of the southern islands are uninhabited, which may be why Cayo Largo seemed like such an unexpected bit of civilization. Whatever the reason, everyone piled out onto the dock to check out the turtle sanctuary, have a cold beer and delight in the resort’s Wi-Fi. There’s a reprieve that comes from cutting the digital cord, but the temptation to reattach is all too strong and in no time noses were buried in phones.

Back on the boat, we took a drive through the Canal del Rosario, a narrow cut with alligators sunning themselves in the mangroves. Then all too soon, it was time to turn back east. Just before hiding for the night back at the lighthouse before our last long leg home, we stopped to snorkel at Cayo Sal. This weather-beaten, low-lying island underscored the dangers of cruising these waters where charts are sketchy and the markers are few. After we anchored, I took my mask and fins and went to check on our hook. Just a few feet away was a 60-foot mast with its rigging still attached. I swam farther and found other odd bits of fiberglass and then finally a rusty old submerged iron ship that was clearly from a different time and a different wreck. The mast was relatively new, and I wondered where the rest of that boat had gone. Hopping into the dinghy, I rode out a mile to the windward edge. There, on a sandbar, sat the deck of a 50ft catamaran now useful for little else other than tying off the dink. Cruising here is not for the faint of heart.

Cuban waters are ideal for anyone who’s had enough of crowded Caribbean anchorages. They’re also great for those who like long sails and challenging conditions. There are also no mooring balls, so you have to know how to anchor well, and resolve any other issues you may encounter on your own. Having seen my share of bars and buoys, though, I was quite content in these remote islands and can’t wait to return.

Cuba is a funky blend of shabby chic Caribbean and retro Soviet glory. It’s like nothing you can imagine because the climate, the Spanish culture and the regime don’t coexist anywhere else on the planet. That mixture itself is enticing enough, but in the remote cruising, the tasty mojitos, the fabulous old cars and the ever-present images of Fidel and Che, and you had better bring a couple of extra camera memory cards. Beyond that, it’s the people that make Cuba so—well, Cuban, a draw that I suspect will pull me back again soon, billboards of wrench-wielding gals notwithstanding. 

FACT FILE

In 2017, 600,000 Americans visited Cuba, the Pearl of the Antilles. Then in November of that year, came restrictions and with them, confusion. But despite the noise in the news, you can still travel to Cuba and have the time of your life.

Travelers must fall under one of 12 categories. The previous “people-to-people” category was eliminated, so “support for the Cuban people” is now the easiest reason for would-be charterers to state on paperwork. This means you have to create an itinerary and document how you will spend time and money in support of the Cuban people and keep receipts in case you’re asked upon re-entry. (Chances are, you won’t’ be.) The key is to spend money with citizens rather than military-run establishments. Think paladares (private restaurants), casa particulares (private house accommodations), privately owned classic car taxis, and experiences like dance or cooking classes.

Dream Yacht (French) is the most familiar charter company to Americans and they have plenty of catamarans in Cienfuegos, a resort town about three hours southeast of Havana. Pay for a guide to take you there and you have another receipt.

Provisioning is sketchy. Stock up before you leave home. And if you plan to bring a handheld VHF radio, bring two and tell them they’re walkie-talkies at the airport. (There’s no understanding of VHF here.)

Zuzana Prochazka chartered with Dream Yacht Charter (dreamyachtcharter.com)

October 2018