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Racing to Havana: Exploring the Growing Regatta Scene between the U.S. and Cuba

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The interest in distance racing to Havana is becoming impressive, with a lot of pent-up interest from Americans. After the surprise rapprochement and the reopening of diplomatic relations between the U.S. and Cuba last December, conventional wisdom suggested that the first regattas might sail in 2016. However, the reality on the water couldn’t have been more different.

In May 2015, Hobie Cat racers participated in the Havana Challenge from Key West, becoming the first American racers to finish on the island in 14 years. While the May race was underway, the Pensacola YC released a surprise preliminary Notice of Race, announcing a 500-nautical mile keelboat regatta set for October 31. Havana Challenge was a spectacular adventure for the 22 participants, with excellent hospitality provided by the Hemingway Yacht Club and Commodore Escrich. Havana is simply a stunningly beautiful city, evoking the feel of a Portuguese or Spanish waterfront city. Commodore Escrich has already announced 11 regattas scheduled from the United States to Havana in 2016.

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Race To Cuba!: Photo by Troy Gilbert
Photo by Troy Gilbert

The opportunities to race to Cuba are getting crowded. Immediately following is the Conch Republic Cup, held from January 27 to February 6. The regatta features five races, from Key West to Varadero, Varadero Offshore buoy race, Varadero to Havana, Havana’s El Malecon Parade Race, and Havana to Key West. With free days to explore and awards parties, this is sure to be a week to remember. If that weren’t enough racing, the Coral Reef Yacht Club and Hemingway International Yacht Club of Cuba will host the 2016 Inaugural Miami to Havana Race, departing on February 10, with a coastal race along the famed Malecón and post-race festivities on February 14. Clearly, the rush is on.

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Historically, the big Gulf Coast distance races to Havana have sailed from St. Petersburg and were first run with schooners starting in 1930. A who’s who of sailing participated in the regattas back then, and the races were part of the Southern Ocean Racing Circuit. One of the more unique stories occurred in 1952 when the first boats crossed the finish line in Havana and were greeted by Col. Batista’s successful coup d’état – sailboat crews were quite literally caught in gunfire exchanges as they sailed into the harbor. The regatta ended in 1959 when Fidel Castro and his revolution eventually took over the island nation.

Race To Cuba!: Photo by Troy Gilbert
Photo by Troy Gilbert

This past summer, Sarasota Yacht Club announced the revival of its historic Sarasota to Havana Race starting on April 2, 2016. Sarasota YC replaced St. Petersburg YC as the organizing body in the 1990s when the race became more of a hot political football than St. Petersburg YC was willing to handle.

In Sarasota’s 1994 race, the sailors were lambasted in a Miami Tribune editorial as “Dangerously naive stooges of Castro’s propaganda,” and crews had to navigate a gauntlet of angry protesters as they readied their boats. Coast Guard, police, and news helicopters buzzed the 85 docked sailboats while sailors stowed gear and supplies and readied sails. Official patrol boats from the Tampa Bay area scoured the harbor, while scuba teams methodically searched the bottom of each vessel for bombs before giving the skippers clearance to head to the race start. Along the waterfront, rumors circulated about an opposing fleet of anti-Castro boats waiting to strike the racers in the Florida Straits.

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Race To Cuba!: Photo by Troy Gilbert
Photo by Troy Gilbert

Sarasota YC attempted to restart their race to Havana in 2011. Heartened by an apparent easing of tensions under a new presidential administration, they officially petitioned the State Department to allow their return to Havana and had 120 early registrations – but were met with silence from the U.S. government. It is highly likely that their 2016 registrations will explode as word gets around to skippers, and crews return from these early races, and the bureaucratic documentation eases from the U.S. government. It should be noted that the Cuban government is making the documentation process quite simple, including issuing visas to sailors at the Marina Hemingway in Havana.

Bob Kriegel, who was instrumental in Pensacola YC’s successful race that started on October 31, states, “Regattas, like any sporting event, are a way for the people of two countries to interact. It’s time for new communications between our people and other countries, as opposed to the severe diplomacy of the past half-century. We first contacted our government, and then, after we were well-received, the Hemingway International Yacht Club. Commodore Escrich in Havana was incredibly enthusiastic about the prospects, and everything just fell into place. What an amazing experience.”

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So Caribbean you can almost taste the rum...

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