For a few sweet years, American cruisers had the freedom to sail to Cuba. It was good while it lasted, says Addison Chan

Cuba has assumed near-mythical properties in the community of sailors around the world. It is almost impossible to utter the name without conjuring up images of rum, sultry latin music and revolution. There is both a bad-boy aura of the forbidden and a seductive call of discovery that make sailors want to visit this island that is unlike any other destination.

As the largest island in the Antilles, Cuba has been influenced by maritime tradition throughout its history. From the treasure galleons of Spain to African slave ships and the sinking of the USS Maine in Havana Harbor, vessels of all descriptions have helped to mold the island into what it is today. Since 1963, however, when the Cuban Assets Control Regulations were put into place to enforce the U.S. embargo on Cuba, American private sailors had all but disappeared from Cuban waters.

Under the embargo, any U.S. sailor challenging the regulations risked severe penalties ranging from fines to imprisonment and confiscation of their vessels by American authorities. Despite the risk of serious consequences, some found the siren call of Cuba too great to resist and came up with various ways to literally run the blockade in order to visit the island illegally. The generally accepted tactics were to sail into Cuba via third countries or to develop “serious mechanical difficulties” that required a port of call to repair.

In 2014, the Obama administration began to re-establish diplomatic ties with Cuba to end a period of estrangement that had been more than 50 years long. One of the most visible signs of the thawing of relations was the loosening of restrictions for Americans wishing to visit Cuba.

The 1963 Cuban Assets Control Regulations that codified the embargo on Cuba outlined 12 valid reasons for Americans to travel to Cuba. Legal travel required a license for one of the 12 categories along with a detailed schedule of activities. In 1999, operators of group tours could apply for what became known as a “people to people” license that permitted them to sell a pre-approved cultural exchange program to Americans who wished to see Cuba legally.

Three important developments took place as part of the Obama initiative to improve relations with Cuba.

1. Licenses for travel to Cuba were to be granted through a process of self-certification, which meant that the decision for qualification rested with the traveler. Previously, permission to travel had to be granted in advance by the Office of Foreign Assets Control, which involved a detailed application and several weeks for approval. With self-certification, travel to Cuba on impulse became a reality.

2. People to People travel, which was restricted to qualifying groups of people traveling to Cuba to study an aspect of Cuba on a pre-approved program, was expanded to include individuals. Group travel was no longer required, and essentially an individual could decide what activities qualified and grant themselves the license to travel. The caveat, of course, was that tourism was still prohibited, but a traveler could study mojito-making on the beach and be perfectly legal provided they followed a full-time schedule and did not call it a vacation.

3. To facilitate the anticipated increases in the number of people self-certifying to travel to Cuba, the requirement to obtain an export permit from the Department of Commerce for an American-flagged vessel to enter Cuba was waived for any visit of 14 days or less.

For sailors, the elimination of the general license application and the export permit requirement meant that all that was required to sail to Cuba legally was to apply for “Permission to Enter the Territorial Waters of Cuba” from the United States Coast Guard. Given the hurdles that existed previously, the single-page application known as the CG3300 was a non-event, and the floodgates were opened for American vessels to sail to Cuba legally.

There ensued a gold rush-like fever that saw a literal stampede of American sailors headed for Cuba, all wishing to have an “authentic experience” before the presence of hordes of U.S. visitors changed the country forever. According to Commodore Jose Escrich of the Havana International Yacht Club, from 2003 to 2015, the only American vessels that reached Cuban marinas were those that sailed in transit to other countries. From 2016 until the present, the Yacht Club has hosted 29 regattas, rallies and other nautical events from the United States, with 744 boats participating. In this same period, 636 Americans became members of the Hemingway International Nautical Club of Cuba.

In the spring of 2016 Marina Hemingway, the main port of entry for American private vessels headed for Cuba, was filled to capacity for the first time in living memory. In the years leading up to the Obama détente it would have been rare to find 50 transient vessels in the marina at one time. Now suddenly there were real concerns about making reservations for space, a common practice in the United States but virtually unknown in Cuba.

The increase in traffic also brought about real prosperity for the people that worked around the marina. Within months many tradespeople, such as electricians, mechanics, sail makers, and carpenters, were able to shift their focus from mere survival to consumer goals like buying a new TV set, or appliances such as microwave ovens and washers. Local paladars (private restaurants) replaced their rickety tables and chairs with new furniture and additional paladars and casas particulars (private bed and breakfast accommodations) opened. Even the government-owned Marina Hemingway made a concerted effort to freshen up its facilities with coats of paint and revamped bathrooms. The pattern was repeated around marinas throughout Cuba.

And then the tide changed with the election of a new American president who promised to take a hard line against the communist Cuban government and ended up strengthening the embargo. In November 2017, the new administration enacted two new policies that dampened the flow of American boats to Cuba as boat owners digested the changes.

The media focused on the elimination of the individual people-to-people license, but that had little effect on sailors who were determined to go to Cuba. By merely changing their reason for travel from “people to people” to “support for the Cuban people,” another of the 12 categories that were not changed, an application for a CG3300 could proceed as usual. The most material change was the inclusion of certain marinas on a list of restricted entities that American citizens were prohibited from using, which was an inconvenience, but they were not showstoppers as there were good alternatives nearby.

It seemed that boaters had been given a pass and the flow of traffic continued, albeit at a reduced rate because many American sailors found it difficult to obtain insurance coverage for their Cuban voyage. Instead of the hundreds of boats that had been expected, the latest rally at the HIYC saw only 54 American boats participating.

The end of the “gold rush” was signaled in May 2019 when the Secretary of the Treasury made the following statement:

“This Administration has made a strategic decision to reverse the loosening of sanctions and other restrictions on the Cuban regime. These actions will help to keep U.S. dollars out of the hands of Cuban military, intelligence, and security services.”

For sailors the reversal meant the exemption from requiring an export permit to take an American-flagged vessel into Cuban waters was cancelled. To eliminate any doubt as to the intent of the change the official position was:

“…to establish a general policy of denial for license applications.”

While it is still relatively easy for an American to travel to Cuba by air following the self-certification procedure that was implemented by the Obama administration, Americans are now prohibited from taking their boats to Cuba legally.

In the weeks and months that have followed the end of legal travel to Cuba by American vessels, the marinas are eerily quiet. Boats that had been stored in Cuban marinas for several years have been removed to other countries out of fear of potential sanctions against the boats and their owners by American authorities. Even the blockade runners of previous years are being extra cautious until they determine if the embargo has new teeth. Until the tide changes, Americans on American-flagged boats can no longer sail to Cuba. Thanks for the memories! 

Addison Chan and his wife, Pat, have cruised extensively around Cuba on their Catalina 42

September 2019