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Double Trouble on the Forbidden Island

Peter Krueger and his well-traveled Double Trouble team continued their adventuring winter ways last week by helping make history in Cuba. After a strong showing at Key West Race Week, the team of Bay Area sailors participated in the first government-approved edition of the Conch Republic Cup from Key West to Cuba. The regatta was forced to stop after 2003 due to pressure and harassment from government officials during the Bush Administration, but relations are now being normalized with Cuba allowing for the first-ever truly legal yacht racing to take place between Florida and the communist Caribbean island nation.

All smiles onboard Double Trouble sailing in Cuba.

Double Trouble
©Latitude 38 Media, LLC

After being delayed for a day by weather, the Richmond-based J/125 Double Trouble took line honors in the 90-mile Key West-to-Veradero, Cuba, race. Covering the course in just 10 hours and 10 minutes, the Double Trouble crew had to fend off Bob Moran’s shockingly quick Annapolis-based C&C 30 Bobsled, which finished second but took first in fleet and overall on corrected time. Once in Veradero — which was described to us as a "rather un-interesting Canadian Euro-trash resort with a big, empty marina and free drinks" — the fleet participated in a single buoy race.

The next portion of the regatta was a light- to medium-air passage race to Havana in which the C&C 30 Bobsled thoroughly drubbed the entire fleet to win boat-for-boat and massively on corrected time. Double Trouble made the most of their Cuban holiday, taking a relaxed approach to the Veradero-to-Havana race. "We were still sailing the boat well, but at some point everyone had a cigar or rum in their hands. We wanted to have fun and take a break from our usual seriousness of racing, so we all switched positions and mixed it up," said bowman James ‘the Hippie’ Clappier.

In Havana, weather again played a factor with an incoming front leading race organizers to bump up the start date of the Havana to Key West race to allow even the slowest boats to make it back to Florida safely. As a result, many entries, including Double Trouble, opted out of this final portion of the regatta to enjoy another day in Havana. "Cuba is a beautiful place with a lot of potential, and it was a cool opportunity to see it right now during its major transition with normalizing US relations. It will be interesting to come back later in life and see how it has changed," added a reflective Hippie. Once the team did decide to return to Key West, they had a quick passage across the Gulf Stream with a jib top up and then an A5 blast into Key West. Double Trouble has now been taken apart and hauled out so that she can be trucked west for a full season of racing on San Francisco Bay and the Pacific Ocean.

Double Trouble’s Conch Republic Cup co-skipper Justin Kromelow and the crew’s tour guide Jesús, who was celebrating his 60th birthday, pose with the StFYC burgee and DT crew members in Havana.

Double Trouble
©Latitude 38 Media, LLC

We’ll have much more in the March issue of Latitude 38.

The Southern Ocean Racing Conference’s Miami to Havana Race begins today, followed on Sunday by a coastal race along the Malecón and an awards party at the Hemingway International Yacht Club in Cuba. Among the 46 entries is one from Mill Valley, MacKenzie Davis’s Class 40 AMHAS.

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Undeniably, the Bay Area has produced a boatload of world-class racing sailors, but one of the local marine community’s greatest treasures is the wealth of colorful waterfront characters who call these waters home.