In 1992, Cuban naval officer Jose Miguel Diaz Escrich needed a job. The Soviet Union had pulled its troops out of Cuba and ended its $2 billion annual subsidy of the island nation, triggering what Cubans call “The Special Period” of shortages and near starvation.
In a country ruled by the Communist Party, Escrich’s answer was heretical: Let’s start a yacht club.
Cuba needed hard cash, and Escrich touted the potential for “nautical tourism.” Late Cuban leader Fidel Castro was a sportsman who could appreciate the value of annual gamefish tournaments and sailboat regattas. Castro’s favorite writer was Ernest Hemingway. The author had lived and worked in Cuba for two decades before the revolution; he had been active in Havana’s pre-Revolution sportfishing scene. Why not name the club and the marina where it was located after Hemingway?

Since its inception, the club has operated or assisted in the operation of the Hemingway International Billfish Tournament, the second oldest tournament in the world.
Throughout the 1990s and early 2000s, enforcement of the U.S. Embargo of Cuba was lax for recreational boaters, and a steady stream of U.S. vessels crossed the Florida straits to taste the forbidden fruit of Havana. With a combination of graciousness, charm and sly subversion, Escrich convinced thousands of foreign mariners to join his club, including prominent American businessmen and politicians.
U.S. Treasury regulations, as interpreted at the time, did not specifically prohibit U.S. citizens from visiting Cuba but they could not legally spend money. This is where the yacht club came in in a sly way. The club would provide U.S. boaters a hosting letter, attesting to the fact that they had been fully sponsored and therefore had not spent U.S. dollars. To get this letter, all you had to do was spend, say, $150 to join the club.
George W. Bush cracked down on this “wink and nod” behavior, fining Americans who visited Cuba by boat. The U.S. Interest Section in Havana, which was later restored to embassy status, sent “spies” with cameras to video transom names and registration numbers on U.S. vessels.

Finally in late 2015, the Obama administration reestablished official diplomatic relations with Cuba, and his Treasury Department reinterpreted the rules to allow Americans to travel to Cuba under 12 exceptions to the travel ban, including travel by Americans in recreational vessels. Now came regattas, rallies and tournaments. During spring especially, American vessels crowded the marina and their owners bellied up to the yacht club bar.
About 90 American boats participated in last year’s 66 Annual Ernest Hemingway Billfish Tournament.
Despite the warming of official relations, Escrich is fond of telling visitors that the club’s status is not assured. As the Cuban government embraces reforms, there is a faction that resents the trend. Escrich’s formula for survival is to continue to grow the club’s membership as a sign of its international importance. The club reports that it has more than 3,000 “socios,” Spanish for members, from dozens of nations.
Escrich predicts that as many as 1,000 people will be on hand to celebrate the quarter-century mark later this month. The club is hosting a Regatta XXV for sailboats on May 19 off the Havana malecon, which is the city’s broad seaside boulevard and gathering place. A hundred boats are expected to participate. There will also be small boat races for Optimist prams, Hobby Cats, Snipes and jet skis.
The next day, there will be a parade and massive photo opportunity during which sailing schooners, megayachts, sportfish boats and craft of all kind will pass in front of El Moro, the iconic lighthouse and fortress at the entrance to Havana Harbor.

Then on Sunday, May 21, the actually anniversary of the club’s founding, there will be a huge party at the club. Escrich said, “I’m glad to communicate you that despite the obstacles and difficulties encountered in its development…Hemingway International Yacht Club of Cuba has become a bastion in the defense and rescue of historic, nautical traditions and a sanctuary for those who love the sea and for friendship and fraternity between members of the international yachting community.”