Sailing a J/88 to Havana, Cuba!?

(Havana, Cuba)- Yes, that is exactly what David Malkin from North Point Yacht Sales in Annapolis did with his team on MI2.  Here is an account of their experience on their blast across the Gulf Stream.

“Sailing into Cuban history.” That’s how T2P.TV’s Ashley Love titled the documentary of her adventure sailing on my J88 M:I-2 to Cuba last February.  Looking back, as we planned for, and then participated in, the first officially sanctioned race to Cuba in over 57 years; it really became apparent we were blazing a new trail. It was more than just another sailboat race.

It was September 2015 when I became aware of the planned Conch Republic Cup race for February of 2016.  A little research revealed what I felt was the perfect combination of adventure and fun. The 10-day schedule called for three 90-mile distance races and two optional in-shore races with lots of parties and sightseeing in between.  Logistics made easy with a common start and finish in Key West with stops in Veradaro and Havana, a perfect triangle of happiness. I signed up before the week was out, relying on the universe to help with the details.  Let’s just say it came through in spades.

In the run-up to the 2016 CRC and since, you can’t pick up a sailing magazine without a mention of Cuba, and for good reason.  That 90 mile sail to a foreign country is a very manageable adventure even for those that don’t have a major offshore passage on their bucket list or a large yacht (J/88 = 29’).  This is clearly highlighted by the 75 boat entry list for the 2017 St. Pete to Havana race.  The majority of entrants are in the cruiser/racer category with many boats under 40’.

Upon arriving in Cuba the first thing you realize is that despite the proximity, I am definitely in a different country.  In our case, we were greeted by the friendly dock staff of the beautiful Melia Marina in Veradaro, home to several nice all-inclusive resorts that our Canadian neighbors have been enjoying for years.  The marina staff and most of the people we met along the way that were associated with tourism spoke English and were happy to see Americans. The Cubans are well versed on US culture as something like 40% have relatives in the US.  Think Spanish speaking Ireland. Their knowledge of US pop culture was made apparently clear when they immediately picked up on the Mission Impossible 2 logo and I was quickly dubbed Tom Cruz.

Cuba is still very much a Communist country. This is not so evident in the heart of Old Havana, our second regatta destination.  Their economic reforms fueled by tourism are happening at a rapid pace.  The Cubans are working very hard to restore Old Havana back to her former glory as capital of the Caribbean.  They are even renovating a pre-revolution structure intended as their capital building that is a scaled down replica of the US Capital building. Historic sights, museums, restaurants, bars and hotels are all benefiting. Traveling outside Old Havana the effects of 57 years of the revolution become evident. The people are warm and friendly, but the infrastructure is certainly suffering.

Our last interaction on Cuban soil was with the customs staff at the Marina Hemingway. At our final check out before leaving for home we bonded over Katie Perry with the customs team. It was a fitting end to the Cuba slice of our adventure. It highlighted how close and yet how far apart we are.

Whether by sea or air, a trip to Cuba should be on all our bucket lists.  For some a visit in the near future may seem a little like roughing it, but it’s worth it.  You’ll get a firsthand understanding of what 50 years of communism looks like.  More importantly, you’ll experience a culture with a fantastic history poised for their next big revolution.

If a race to Cuba sounds good, you’re not alone.  Adventure racing combined with fun destinations is the formula that is fueling the fastest growing segment of the sailboat racing market.

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