Captain Stacey Brooks on Sailing and Visiting Cuba with Sea Dog Sailing

By: Destinations, Sailing Story, women on the water

Cuba Libre

As the wheels hit the runway in Havana, I gasped with the strong realization that I was finally fulfilling this lifetime dream. After all my years at sea around the Caribbean and the world, deep in my soul, I had always wanted to experience and sail Cuba. The largest island nation in the Caribbean sea, ironically the closest to the US, and yet I had never been there. In fact, a lot of Americans have never been there. All the more reason to go. The controversy, as well as the severe beauty and contradictions, have tugged at my wandering soul for years.

Our plane taxiing to the Jose Marti International Airport, I listened to the chat around me in the plane. We had luckily been upgraded on our small jet. Sitting beside us was a true mix of people and backgrounds. Three Americans who worked at the US Embassy and who told me they were in “facilities management” sat up front with us. When I enquired what that meant exactly, they quickly changed the subject. The mystery and intrigue begins. Two mechanics flew up front with us as well. Apparently, US planes going in and out of Cuba fly with their own parts and mechanics. When I enquired why they told me that it was a trust issue as well as a labor and parts requirements. That said, we grabbed our bags and descended down the stairs onto the steamy hot runway and walked into the terminal.

My heart was racing as I approached the immigration officer. Why am I so nervous? After years of hearing and reading about clandestine experiences in Cuba, as well as all the American warnings, I suppose I was finally addressing that in person. The immigration officer grabbed my passport, along with my Cuban Visa which I purchased with no problem in Houston, smiled, told me to look into the camera and move on. I walked through the lime green door with cracked glass straight into 1959.

Sailing in Cuba

Cienfuegos was our home base for our sailing charter out of Cuba. Sea Dog Sailing Inc has traveled all over the world taking customers to challenging and unknown venues but Cuba was a place that threw up the sorts of barriers that had made me nervous. Soon, my fears fell away though as we met the small charter base crew of Dream Yacht Charters. Managing about 20 boats, mostly cats, the French company has actually done a fine job at maneuvering around Cuban politics and adhering to sometimes bizarre regulations and more. They have a solid relationship with the community, customs and immigration. The Dream Yacht crew, from the office manager to the dock hands, made our time sailing in Cuba worry and problem free.

While always prudent and obviously necessary, all the charting and research I do for sailing trips never prepares me for the actual adventure. This can be beautiful or a hard reality but either way it is what makes my love for travel and the sport of sailing continue to bloom. As we sailed south more than 110 nautical miles towards Cayo Largo and her surrounding islands, I was reminded yet again that the love of sailing and the sea has transported me to some of the most glorious spots on this planet. This beautiful, wild world awaits anyone who has the drive to really see and not just look. The need for iPhones, the internet and the constant addiction to connection has actually left us sadly disconnected. Imprisoned by technology, we roam around like lobotomized human shells unable anymore to just take things as they unfold. The art of surprise is what nature and the world will continue to show us if we can just put down our phones long enough to see it.

Travel To Cuba

Shortly after our return from Cuba, the Trump administration unfortunately decided it would be a good idea to severely limit communications with Cuba even more by tightening travel restrictions and banning yachts and cruise ships from visiting her shores. It doesn’t really matter what “side” you are on – whether you are right or left or somewhere in between. What really matters is stopping to seriously think about this issue for a second – or a minute -or better yet take an hour and do some in depth research. With all the countries we as Americans deal with in this world and with all the pain and peace that has come out of either shunning or forgiving other nations, somehow we continue to have an obsession with a small Caribbean nation that poses zero threat to us politically, economically, socially or otherwise. Cubans are just humans – exactly like us. They have families and friends and experience sadness, love, happiness, joy, pain – just like us. Time to move on.

Moving on through the beautiful sport of sailing, whether in Cuba or any other amazing spot on this vibrant planet, is one of the deepest learning experiences any human can acquire. Put down your phone. Turn off your computer. Stop reading this article and get out there! You will be a better, smarter human and the world will thank you for it. Fair Winds!

Sea Dog Sailing, Inc highly recommends the VIA HERO APP and their staff. Excellent app for traveling to not only Cuba but several other countries and cities in the world. Sea Dog Sailing, Inc also highly recommends Cayo Largo Marina and the long time manager Pire. He is warm, helpful and friendly to all yachties no matter their nationality or background. Make sure you look him up on your sailing adventure to Cuba and tell him Stacey and the girls say hello! 

Sea Dog Sailing, Inc is a 15-year-old American Sailing Association School that is proudly owned by USCG Captain Stacey Brooks (ASA Instructor since 1997). She teaches in different venues around the world and continues to take students and customers to exotic sailing destinations each year. In 2019 she is traveling, along with her first mate Allison Beauvais, to Cuba, Spain, Thailand, and Greece. For more information on her, her company or up and coming sail trips please visit her website at .

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Doran Cushing
Doran Cushing

Having been to Cuba 10 times now since 1991, I can appreciate Stacey’s experience…it is always positive when it comes to the Cuban people and authorities. Pire, the dockmaster at Cayo Largo, was a translator for Fidel and when Trump’s latest brain fart about the cruise ships going to Cuba was announced, Pire expressed it simply. “This will only hurt the Cuban people, not the Cuban government.” The Cuban people share a beautifull country, universal health care, free education to the highest levels, no drug problems, no gun problems. Yes, Old Havana could use a paint job. If that’s what… Read more »

Tony Castro
Tony Castro
Reply to  Doran Cushing

Doran sorry I think you missed the boat
Nice folks great benefits to living in Cuba……..
However you as US citizen had the freedom of choice
and wearwithall $ to travel to Cuba those folks DO NOT
When did you ever see a Cuban tourist

doran cushing
doran cushing
Reply to  Tony Castro

Actually, Cubans in different specialties travel to the US…athletes, musicians, artists, educators, medical professionals. Tourism is not the priority for the Cuban government…long crippled by the US embargo…”El Blocado” as they call it. If you explore the issues you will find many answers…most of which are not talked about in the US scheme of politics.


I wouldn’t cloud the adventure opportunity with politics that go back to the 60’s. Cuba is not insignificant as you already conceded its proximity to our homeland. They will “rent space” to anyone who may be a threat to your fellow citizens. Be grateful you were able to enjoy a rare opportunity, but stay out of things you obviously don’t understand.

Doran Cushing
Doran Cushing
Reply to  JONATHAN

Jonathan, how many times have you been to Cuba? Do you know, for example, that any commercial ship that stops in Cuba cannot come to the US for 6 months? Ponder those implications to “free trade.” That’s only an opener. YOU obviously don’t understand our Cuba policy and the Cuban system…a social democracy/not communist by any definition.