As relations with Cuba continue to improve, sailboat races are returning to the long-forbidden island nation. The first of these, the Havana Challenge, took place from May 15 to May 21 when a group of American Hobie 16 sailors from Key West, Florida, raced to Marina Hemingway in Havana. Event organizers applied for and received the necessary permits, making this the first U.S. Government-sanctioned race to Cuba in 50-plus years.
The three-part event consisted of a 30-mile Gulf Stream Shakedown, followed the next day by a Havana leg, which brought the fleet across the Gulf Stream to Cuba. After that, came The Malecón, a series of inshore races that pitted Yankee sailors against their Cuban counterparts—including Cuban Olympic sailors and the Cuba National Sailing Team—in front of Havana’s iconic Malecón esplanade.
The Havana Leg kicked off at 0730 on a Saturday with a Le Mans start in Key West that saw an armada of five Hobie 16s and 14 support vessels setting off onto the 90-mile course, with the first boat arriving at the Marina Hemingway around 1715 that evening. En route, the competitors saw sustained winds of 18 to 20 knots, with gusts to 25-plus knots, and seas of up to 12 feet—tough duty for small beach cats.
“Forty percent of the fleet got ripped apart. One boat wouldn’t go any farther than Marina Hemingway,” said Capt. Joe Weatherby, who served as one of the event organizers, of the boisterous offshore conditions. “The piece of sailing they did was freaking heroic!”
Fellow event organizer Capt. George Bellenger and his (rotating) crew took line honors in Cuba, but—just as importantly for the event’s goal of fostering cross-cultural relations—the Cuban nationals mopped the racecourse with the Americans during the inshore portion of the regatta.
“They kicked our butts—it was spectacular!” said a delighted Weatherby, adding that organizers plan to turn this race into an annual affair. “Next year, we’ll take 500 raceboats down there!”
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