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How I Worked the System To Sail Into Havana Harbor in Cuba as an American

Havana Cuba 10 photos
Photo: wikipedia
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Several days ago, I posted an article here on autoevolution, where I talked about some of my experiences with taking guests aboard my boat. In the days following, I heard from some readers who asked me to pen other stories about my experiences; so here goes!
In the early 60s, the U.S. imposed the most enduring trade embargo in modern history on Cuba, just 90 miles across the Strait of Florida to U.S shores. The embargo prevents American businesses and businesses organized under American law from doing business with the island nation. In addition, for years, the act prevented U.S. citizens from visiting.

In October 2016, President Obama eased trade, travel, and financial restrictions that had been in place for decades. Then, along came The Donald, who reinstated the embargo, but did leave the door open for U.S citizens to visit as long as they were traveling in an official capacity and not as tourists.

My adventure to Cuba happened prior to the easing of any of the restrictions for U.S. citizens. I had sailed from Fort Lauderdale, Florida, to the island nation of Jamaica which took me around the southeasternmost tip of Cuba with Haiti on my port side. I rounded Punta de Maisi, Cuba, and headed straight to Port Morant in Bowden Harbor, Jamaica, staying clear of Cuban waters.

I had only planned to stay a few days, then head west for a stop on Grand Cayman, then around Cuba's west coast on my way to Key West, Florida. However, a falling barometer indicated bad weather was on the way, so I holed up for a few days until the weather passed.

I left the protection of the harbor at sunrise with favorable winds out of the southeast for the 300-mile (482 km) 2-day passage to Grand Cayman.

I arrived in Grand Cayman as planned and did what sailors do; head for the nearest watering hole after anchoring off the aptly named Rum Point. Again, I had only planned to stay for a couple of days, but I ran into a great group of sailors who I helped with some issues with their boat.

While having one of our many conversations, they explained that they had just come from Cuba. I had always dreamed of visiting Cuba, but the aforementioned restrictions prevented it. I grilled them on how they were able to visit as American citizens. They explained that they had run into an old salt in Turks and Caicos, and he outlined how American seafarers could legally get into the country.

It goes like this: Rounding the island's western tip on the way to Key West puts you on a northeastern heading. Favorable southeast trade winds (the same winds I rode to Grand Cayman) will take you past Havana, Cuba's capitol and largest port, on a starboard tack. Once you reach the longitude of Havana, you radio the U.S. Coast Guard stationed in the Keys to report engine problems and ask to be cleared into Havana Harbor.

Once cleared to enter the harbor, you will be met by a harbor master who will want some sort of payment to stay until you can repair whatever ails your engine.

The old salt had warned them that if you do get clearance to Cuba under these circumstances and their next port-of-call would be somewhere in the U.S., the coast guard would board their boat at some point, check their logs, and ask for proof that they were in fact, had an engine problem.

I sat there glued to their every word and could not imagine it would be that easy but nor was I determined to try as I wanted to get to Key West for the annual Ernest Hemingway look-alike contest.

I left Rum Point after several days and headed west, all the while thinking about trying to get into Havana Harbor as described. Could I really pull it off? Nah!...well maybe!

I had a while to mull it over as it was about a 2-day sail to reach Havana. Back in forth in my head, I went, but once I was able to see the early morning lights of Havana Harbor, I decided to give it a go.

I followed the instructions just as they were explained to me, and within 30 minutes of contacting the Coast Guard, I was given clearance to enter the harbor and moor while my engine was being repaired. I was in disbelief, and my nerves were frayed, to say the least.

I went in under sail (because my motor was broken) and was met by a young Cuban man in a Zodiac who towed me to a mooring buoy as I dropped my sails. He spoke some English, but to my surprise, my years of Spanish resurfaced, so we had no problem communicating. He suggested that I get someone to stay aboard my boat while I'll be ashore and offered to be the guy. He commanded a whopping 100 Cuban Pesos ($4.50) per day.

All told, I spent five glorious days in and around Havana and loved every minute of it and was sure to pick up some random spare parts to show the Coast Guard if I got boarded.

Sure enough, on my way to Key West, I was approached by an inflatable Coast Guard gunboat and boarded. First, they grilled me about the location of my gun. It took about thirty minutes to convince them that I did not have a gun on board. In the end, I showed them my log and the spare parts I purchased and was sent on my way!

Some of you may be wondering whether or not I would do it again; you bet!  The Cuban people were the most gracious people I have encountered outside of Thailand. The food was amazing and the cocktails were top-notch. It was a trip back in time in many respects and there is nothing I appreciate more than the perserverance of the populous of Cuba who have endured so much suppression.
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