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Cuba: chartering a bareboat

For the crew of Velasquez, one of the best moments on the south coast of Cuba this spring was the day they caught a big red snapper while sailing off Cayo Macho de Afuera.

Club Cienfuegos is a government-run, prerevolutionary yacht club on Cuba’s southern coast.

The cruising guide says locals on this small but gorgeous sandy island will cook up whatever you bring in, so the six crewmembers dropped anchor and jumped into the dinghy with the fish in a pail and cold beers in a bag. There was nothing that looked like a restaurant, but a local they met at the end of a long and rickety dock turned out to be the cook. He walked them back to a little house, with a cooler full of lobster tails, and negotiated the meal.

“They spoke no English, and we had no Spanish, but 30 minutes later we were all drinking our beer in the shade of a small thatched hut, looking out at the lovely beach and the azure water, and eating a lunch of fresh lobster tails and red snapper, rice, cabbage and orange slices,” says Chris Freitag, the skipper aboard Velasquez, a Bali 4.5 catamaran. “The whole experience was fabulous.”

Lessons learned: cruising Cuba’s southern coast By Stephen Blakely Government regulations limit where and how you stop along the way. Even after clearing Cuban immigration and customs, on a boat you also have to clear in and out of every port that has a Guarda Frontera base. Keep your passports and “dispatcho” from the previous port handy. You’re on your own out here. The Guarda Frontera does not help boats in trouble, there are no towing services, and many local fishermen use rowboats. Don’t expect help. Provisions are a struggle. Many staples are in short supply, the Cienfuegos charter base can’t fill many items on the menu, and reprovisioning underway is unlikely. Unless you catch fish, learn to love chicken and ham. “At the marina commissary you can get 60 to 70 percent of what you need. Buy the rest in markets in the city. Specialty items, such as parmesan cheese, you should bring from your own country,” says Omar Morales, the base manager at Platten Sailing Cuba in Cienfuegos. “The Germans are even more spoiled than the Americans when it comes to delicacies, but you’ll never starve in Cuba.” Nautical charts in Cuba are excellent. Charter firms provide very good paper charts, but we brought our own from NV Charts ( Bring a mobile chart plotter to use at the helm (cabins have a fixed unit). Cuban aids to navigation follow International Rules (triangular red to starboard on returning, square green to port) and are well-maintained. A VHF radio is essential. Wireless Internet is sharply restricted, and cellphone service is limited. There are no real-time radio weather forecasts in English. You will be off the grid. Don’t trust the drinking water. We brought lots of bottled water and purified Stravinsky’s freshwater system with chlorine. The fishing is wonderful. Our group caught a wide variety of fish, using both lines and spear guns. Lobsters are illegal to catch, so buy them from locals. The “people-to-people” program works. The 10 days we spent on the water with Alberto and Odile, the two local Cubans, built bridges that both sides will never forget. “I can truly say my experience would not have been as great as it was without the two locals,” says Ajai Nemani, a New York doctor who cruised on Pollack, a Lagoon 39. “They treated us like family, and we got to know them well. Through our days and conversations, I learned that we have so much more in common than not, despite having governments that are worlds apart.”

For me, the highlight of Cuba came several days later when our little fleet sailed to a similar delicious lunch at Cayo Rico, a stunningly beautiful, deserted and quintessential tropical island with a blazing white beach surrounded by electric-blue sea. That afternoon we spent a couple of hours snorkeling in gin-clear water at Hijo de los Ballenatos — the healthiest coral reef I have ever seen — as a school of blue tang thronged around me, several big tarpon flashed by for a visit, and a lazy stingray guided me through the reef. That evening, safely tucked away in a protected anchorage, three of our boats cooked up a gourmet potluck dinner and partied late into the sultry Caribbean night.

Fun aside, bareboat chartering in Cuba is a serious endeavor. It takes a few long days of sailing to get to places such as this, the cruising grounds are shallow and remote, and if something goes wrong you can be in real trouble. Unlike our Coast Guard, the Guarda Frontera (Cuba’s coastal security force) will not come to the aid of vessels in distress, private towing services don’t exist, and going aground on the unforgiving coral can be a terminal experience. Our boat, a 50-foot Catana catamaran named Stravinsky, was a last-minute replacement for Beethoven, which a few weeks earlier struck a minor key (no pun intended) and sank, a total loss.

That’s not unusual: Bareboat firms in Cuba have lost seven boats in the last 14 years and suffered “tons of crashes,” says Omar Morales, the base manager at Platten Sailing Cuba in Cienfuegos. “Cuba is not easy for beginners. Lots of clients sail at night — a big mistake — and this is what happened to the Beethoven.”

SPECIAL DELIVERY: Buy local lobsters; harvesting them yourself is illegal.

For decades, only Canadians and Europeans could enjoy bareboat chartering in Cuba. Now American boaters can, too, but only with careful arrangements and only if you understand the limitations and demands of sailing here.

I was among the first organized charter group of Americans to cruise Cuba’s south coast, in April, with three dozen very experienced sailors on seven bareboat catamarans. Cuba’s waters were as new to us as we gringos were to most of the Cubans we met.

“In 27 years, this is the largest group of Americans I’ve ever seen here,” says Pire, the ebullient and multilingual harbormaster at the marina on Cayo Largo, Cuba’s first and well-appointed tourist resort island. “Most of the customers we get here are Italians, Canadians and Russians.”

Having chartered in the Bahamas and the U.S. and British Virgin Islands, I found Cuba’s Caribbean cruising grounds more demanding. The waters are more open, the islands are low and unsheltering, the anchorages are farther apart and more exposed, and the shoreside facilities are very few, far between and limited. This is territory for serious boaters who know what they’re doing, are fully provisioned and self-reliant, and are able to take care of themselves.

That being said, I have never seen such pure, powdery white sand, perfect palm-tree-lined beaches and mesmerizing cerulean water, or snorkeled through such fish-filled coral reefs, with almost no one else around. Whatever else it has meant for those on land, Cuba’s isolation from the modern world has been a blessing for its waters and all that lives within.

Where and How

Bareboat chartering is relatively new in Cuba. The southern city of Cienfuegos is the only base. Just three charter firms offer a total of three dozen or so boats, almost all sailing catamarans. We used Dream Yacht Charters, a French firm.

Under current U.S. rules, generally only group visits by Americans are allowed into Cuba, using one of the 12 U.S.-approved classes of travel. “Vacation” and “pleasure” travel are not authorized; our trip was classified as a “people-to-people” visit. We chartered seven sailboats, using a Cuban-American travel agency to handle all the tickets, visas and paperwork.

There are only two cruising destinations on the south coast — separate offshore island chains stretching to the east and west, each a full day’s sail away. To the southeast is Jardines de la Reina, considered the biggest and most unspoiled coral reef in the Caribbean, where a young Fidel Castro liked to dive. It is now a protected and sprawling national park of low mangrove and shallow islands, with stunning and fish-filled reefs.

To the southwest is the Canarreos Archipelago, with some of the most pristine and remote beaches in the Caribbean. The western end of this chain is anchored by the large and distant Isla de la Juventud, part of which is a national park.

Cuba’s south-coast cruising season runs from January to April. In the 10 days we spent in Cuba we had no rain, rarely the “typical” trade winds out of the northeast and very few bugs.

The Trip

The historic fort Castilde Jagua was built to protect Cienfuegos from pirates. (Below) A typical breakfast is served aboard Stravinsky.

I went with the La Trappe Creek Society, a unique group started in 1971 by four close boating friends that has grown into a devoted network of several dozen experienced sailors who charter all over the world. The Society — “Creekers” within the tribe — is unincorporated and has no official bylaws, rules or dues; members just pay trip costs.

For an all-male group that has more than its share of doctors, lawyers, business owners and other Type A personalities, they are a remarkably adaptable, low-key and congenial bunch on board. “One of the unwritten rules is that our guys leave their egos at the dock. If you don’t, you’re ribbed about it unmercifully,” says Jay Kenlan, a Vermont lawyer and longtime commodore of the Society.

Our Cuba trip began with a group breakfast in a Miami airport hotel, followed by a 90-minute flight to the tiny airport at Cienfuegos. By midafternoon we had arrived at the city’s gleaming-white prerevolutionary marina and moved aboard our seven catamarans, ranging from a Lagoon 39 to a Catana 50, storing provisions and going through the check-out process.

The next morning, as a Guarda Frontera officer went down the dock completing his paperwork, our boats slipped their lines and headed out one by one. After an hour of motoring through sprawling Cienfuegos Bay, we entered the Caribbean and raised sails, bearing east for the Gardens of the Queen. In what became a daily routine, the breeze began to die in early afternoon, and the engines came on. By evening our fleet was anchored off tiny Cayo Blanco just inside the Jardines de la Reina National Park. For dinner we dinghied ashore to a government-run beach shack for excellent lobster and chicken paella, cold drinks and a colorful sunset.

Because of the many unknowns with this trip, the Society hired a local pilot and interpreter (Alberto) and a mechanic (Odile) to come along, an excellent decision. We had enough mechanical breakdowns among the seven boats to keep Odile busy, and he proved especially valuable in helping to kedge off Virgin Buoy, a Leopard 40 that went aground, luckily escaping with no damage. Both were also expert fishermen and cooks, introducing the Americanos on their boat to the local delicacy of fresh-caught barracuda. (North-coast barracuda have a toxin that causes ciguatera, a foodborne illness, but Cubans say those on the south coast do not.)

We split our time between Jardines de la Reina to the east (where the diving is better) and the Canarreos Archipelago to the west (where the beaches are better). So after two days of sailing into the national park, where one boat saw a massive whale shark glide past, the fleet turned around. Our longest day, more than 60 miles, took us far offshore and ended below the soaring red-and-white lighthouse on desolate Cayo Guano del Este, marking the start of the Canarreos chain.

Cayo Guano is low and shallow, offering little or no protection from wind and waves — typical here. That night our master chef and musician, Mike Frizell, served up a delicious dinner of chicken and rice, followed by a guitar concert. Conversations among our six crewmembers curved through history, literature, science and other well-informed tangents. The warmly lit cabin became a cozy and congenial refuge from the black, windy and lonely sea outside.

Cayo Rico is a quintessential tropical island with white beaches and electric-blue water.

The next day included the annual “Tucket Bucket” race (the prize being a yellow beach bucket from Nantucket) of about 50 miles down to the marina at Cayo Largo. As the last of our boats tied up that evening, Pire, the harbormaster, came aboard to expedite the Guarda Frontera clearances. This attractive government-owned marina was the only support base outside Cienfuegos that we saw in 10 days of sailing. (For more on Pire and Cayo Largo, visit

The following day included the lunch at Cayo Rico and snorkeling at the reef. Our next-to-last day was spent motorsailing into the wind back east along the long shore of Cayo Largo and anchoring again below the lighthouse at Cayo Guano to stage for the final leg.

The next day we were guided back to Cienfuegos Bay by a unique coastal navigational aid: the hulking concrete ruins of the Juragua nuclear power plant. This $1 billion project was abandoned near completion in 1992, after the Soviet Union collapsed and suspended its economic aid to Cuba.

By midafternoon we re-entered the protection of Cienfuegos Bay and before long were safely tied up again at the marina dock, our Cuban cruise successfully and safely over. Our final day involved a land-yacht trip to the UNESCO World Heritage city of Trinidad, a perfectly preserved Spanish colonial settlement an hour’s drive down the coast to the southeast. It was a great way to see more of the main island and its residents, including, unfortunately, local street hustlers known as jineteros.

As our trip ended, my sense was that Cuba is already being changed by the ever-growing presence of American visitors. Cienfuegos is the gateway to Cuba’s Caribbean coast and has a clearly growing tourist sector, as seen by the many paladares (private restaurants), casas particulares (private rental rooms or hostels), the pirated American shows that play on some restaurant televisions and other signs. The bareboat firms there are pushing to expand, and it’s inevitable their American customer base will grow.

In many ways, Cuba is still a nation “encased in the amber of the 1950s” by a dictatorial government and still-potent U.S. embargo. But as our little voyage and new friends demonstrate, the amber is starting to crack.

If You Go

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Bareboat charter firms in Cuba (Cienfuegos)

• Alboran (Spanish):

• Dream Yacht Charters (French): dream

• Platten Sailing (German):

Cruising Guides

• Cheryl Barr, Cuba Cruising Guide, Vol. 1, Western Cuba, Vol. 2 for Eastern Cuba due in the near future, (2015, $60, Yacht Pilot Publishing).

• Nigel Calder, Cuba: A Cruising Guide, (1999, $85).

• Amaia Agirre and Frank Virgintino, A Cruising Guide to Cuba. (PDF download)

Useful Sites

• “FAQs About the New Visitation Rules,” U.S. Treasury Department (Sec. II, Travel). Documents/cuba_faqs_new.pdf

• “Crown Jewel of Cuba’s Coral Reefs,” New York Times, July 13, 2015.

• Cayo Largo, Cuba.

This article originally appeared in the August 2016 issue.