Gulfstream Politics—Racing Hobie 16s to Cuba from the USA

by David Schmidt, Sail-World USA Editor on 22 May 2015 Forget about geopolitics: For sailors, the greatest aspect of improving U.S. relations with Cuba is the return to the Halcyon days of sailboat races from the mainland USA to this long-forbidden island nation. If this sounds like a pipedream, think again, as the three-part Havana Challenge unfolded from May 16-21 and brought a fleet of five Hobie 16s, supported by 14 chase and support vessels, from Key West, Florida to the Marina Hemingway in Cuba.

The event was the brainchild of Captain George Bellenger, who was supported in organizing the event by his wife, Captain Carla Bellenger and Captain Joe Weatherby, all of whom reside in Key West, Florida, and all of whom are highly experienced sailors and mariners. In fact, the Bellengers made this passage several times in the late 1990s and early 2000s aboard small Hobie catamarans, but this below-the-radar behavior was wisely curtained in 2001. Still, these pre-911 experiences allowed the Bellengers to befriend members of the Cuban sailing community, and to build the kind of relationships that would allow them to successfully organize this event. According to Weatherby, the trio applied for their permits in August of 2014 and were granted the necessary permissions by the Treasury Department, the Commerce Department, and the United States Coast Guard, making this the first U.S. Government-sanctioned race to Cuba in more than 50 years.

In order to ensure the fleet’s safety, the event started with the 30-mile Gulf Stream Shakedown, which gave teams a final chance to check their equipment and communications gear, before the offshore leg, which took place the next day. Once in Havana, the event also included The Malecon, which was a series of inshore races that pitted the Americans against talented Cuban nationals.

The Havana Leg started at 0730 hours on Saturday, May 16 and was wrapped up by evening, with the first boat—skippered by George Bellenger and a rotating crew—arriving at Marina Hemingway at roughly 1715 hours. En route, the competitors saw sustained winds of 18-20 knots, with puffs to 25-plus knots, and seas of up to 12 feet. According to Weatherby, two boats were destroyed, while another one was rendered inoperable upon arriving in Cuba. Fortunately, everyone arrived safely and, with the help of the racers and some Cuban locals, the boats were repaired in time for the The Malecon.

Here, the Cubans dominated, crushing their American friends and allowing sailors from both sides of the Gulf Stream to enjoy a friendly cross-cultural exchange.

According to Weatherby, the event was a huge success, and one that the organizers hope to turn into an annual affair. So, if the idea of adventure racing to a once-forbidden island nation, while negotiating 90 miles of offshore sailing-including the Gulf Stream-sounds like your kind of sailing fun, be sure to stay tuned for updates on next year’s race.