Until the fall of Cuba to Castro and his revolutionary forces in 1958, sailors actively raced schooners in the 284 NM St. Petersburg to Havana Race, which from 1930 to 1958 was considered a highly prestigious event and eventually became part of the Southern Ocean Racing Circuit. After the American embargo and the heightened tensions during the Cold War, the regatta ceased as did the flow of competitors and boats from as far away as Europe and the Caribbean. It wasn’t until the 1990s that efforts were made by South Florida organizing bodies to re-establish the regatta. While successful, the races were highly controversial with sailors described as “dangerously naive stooges of Castro’s propaganda” in the Florida newspapers. Anti-Castro protests were held outside the yacht clubs as racers prepped their boats and police scuba teams methodically searched the bottoms of each vessel for bombs before giving the skippers clearance to head to the race start. Rumors were always heavy on the piers of a belligerent fleet of anti-Castro boats waiting to strike the racers in the Florida Straits.
One of the more unique events in the history of this regatta occurred in 1952 when the 29 participants, escorted by a U.S. Coast Guard cutter, sailed into Havana Bay and immediately came under gunfire. Col. Fulgencio Batista had timed his successful coup d’etat on the island to coincide with the regatta and the international press on hand for the event. As calm descended on the island, trophy presentations were held in the harbor, albeit under the watchful gaze of Cuban troops and tanks.
Races to Havana from the Florida ports of St. Petersburg and Key West continued during the 1990s, until the U.S. government began making the permitting process more difficult and cumbersome. The final death knell came in 2001, when President George W. Bush issued executive orders furthering the embargo of Cuba, making it illegal for any American to visit the island. The U.S. Coast Guard reacted quickly to shut down the lingering regattas and threatened to seize participants’ boats under the reasoning that these recreational sailors were propping up the Communist regime.
The last attempt to restart this historic sailing regatta occurred in 2011, led by the Sarasota Sailing Squadron, in hopes the Obama administration would be more willing to allow this event. The club officially petitioned the State Department for permission to race to the island and billed it as a cultural and humanitarian exchange – a way to bring up to $50,000 worth of Optimist sailing gear to the children of Cuba. More than 120 boats had registered for the race, but the organizing body was met with silence from the U.S. State Department. All further attempts were then shelved.
Last December President Obama announced the United States would resume diplomatic relations with Cuba as well as ease certain travel restrictions and minor aspects to the trade embargo. Within 24 hours, the chatter from race organizers started and meetings were scheduled to discuss this new window of opportunity to restart the historic regatta.
Cuba has beckoned to racers since the 1930s and with these current steps towards the normalization of relations between the United States and Cuba, this could open the floodgates for American cruisers and racers alike. Expect a rapid push for a return to these historic sailing regattas beginning in 2016 and eventually an effort to recruit boats from the United Kingdom and Europe, which are already running the Caribbean circuit.