Havana Challenge

The Havana Challenge is an amateur sporting competition designed to promote person-to-person intercultural exchange through the sport of sailing.  Thousands of Cuban citizens will be able to participate in the event by watching races from the Malecon, in Havana.  Many will attend the awards ceremony as well.

When it comes to adventure, an extreme sports competition is the ultimate experience. The Havana Challenge elevates the feat with a surprise guest star, the forever unpredictable Mother Nature. Past trial runs performed by the event’s organizers demonstrated unscripted drama with 20-foot seas, 30mph crosswinds, a near-fatal collision with a breaching whale, a busted 15-foot mast, and a welcome party of machine gun-toting policia!

The 2015 event saw about 100 Americans in around 20 sailboats arriving at the Cuban capital On May 16th from Key West, Florida.  The Hobie Cats were accompanied by support vessels, including two replicas of 18th century schooners.  Five U.S. teams took on five Cuban teams off Havana’s iconic Malecon seaside walk in Hobie Cats.  A maritime parade was held on the following day in Havana Harbor.

Our American adventurers became guests of Commodore Jose Miguel Diaz Escrich at the famous Marina Hemingway – where they were defeated by the Cuban Olympic Sailing team. A small penance to pay for building a unique relationship worth exploring.

The Havana Challenge organizing committee worked successfully with Commodore Escrich to obtain all of the necessary permits and permissions to launch the inaugural event in May 2015.

With the success of the Havana Challenge, the organizers plan to incorporate the same Hobie Cats to develop a 10-stage “extreme regattas” – that will sail around the world across famous bodies of water, explore exotic historic locales, investigate local maritime superstitions, connect diverse cultures, and feature a cast of international (some would say insane) sailors who will compete against each other and Mother Nature.

Click here to view the 2016 Havana Cat Challenge highlights.