The Cuba Logs, Part 1

Cuba Flag

 The Cuba Series which starts below is a collection of Logs which describe the conceptualization, planning and execution of our cruise to Cuba aboard our Fleming 65, Sequoia.  This cruise took place between March 26 and April 6, 2017.


I cannot recall when we first contemplated taking our Fleming 65, Sequoia, to Cuba.  Perhaps it was during one of our trips to the Abacos.  We had made the trip to the Abacos from Oyster Bay, NY a couple of times and were contemplating taking Sequoia another 800 miles south to the Exhumas.  In short,  it was time for Melinda and me to look for another adventure.  While the Abacos were enjoyable, we had familiarized ourselves with the area and started to get that restless feeling.  Been there, done that.  We were ready for new places, new experiences and new cultures.  The problem with the Exhumas is that there is really no there there, mostly low lying islands without much civilization with little protection when the winds turn to the north.

Cuba certainly seemed exciting and would fit the bill well.  And we wanted to get there while it was still fresh, unspoiled by hoards of real estate developers and possibly casinos.  After all there was the romanticism of Hemingway and the days of mafia control when it was a strange and unique extension of the United States.  And then there were the cars which captured all the colors of the Caribbean and reminded us of our childhood days back in the 50's and 60's.  You know what I mean, that warm fond feeling when the United States was a kinder, gentler place when parents let their kids out of the house in the morning and urged them to be home before dark.  There was little fear for children's safety because the neighborhood was like a family.  After all, everyone had been through the Great War together.  The people of the United States were a team devoted to taking care of each other.  Well perhaps not, after all there was McCarthyism and then again there were the assassinations, JFK, Robert Kennedy and Martin King. Well at least I liked to remember the United States that way. I am sure many of us do.

The ability to take Sequoia to Cuba without substantial financial and legal risk changed dramatically with the Obama administration which was going to great lengths to normalize relations between the two countries.  Easing the enforcement was one thing but the big item was allowing US companies to undertake business relating to Cuba.  Specifically until the new US Treasury guidelines were issued last spring,  US insurance companies could not provide insurance for US  boats in Cuba.  This was left to foreign players like Pantanious who would charge $15,000 for the privilege of letting you take your insured boat to Cuba for two weeks.  With the opening of the market to US insurance companies the cost of insurance for the boat dropped to an incremental  $1500 to our existing yacht insurance policy with ACE for a period of two weeks.  It is important to emphasize that the practical requirements of cruising to Cuba for Americans have changed dramatically in the two years prior to the latest presidential election.  Thus what seemed difficult or impossible two years ago has become much more easy and commonplace.  In other words, when we started working on this project, it was pretty fresh territory for cruisers as well as American insurance companies.  At the same time, there have been Americans who have traveled to Cuba both with their boats and otherwise for years but have done so illegally.  This is not an option that we considered nor would we consider.  The approach we took and recommend is to follow US and Cuban laws and regulations scrupulously.  There is too much at stake personally and financially not to do so although we acknowledge plenty of people have gotten away with breaking the law.

Our investigation of the intricacies of taking our own boat to Cuba began with a call to Pat Flaherty of Burr Yachts. Burr is the East Coast Fleming dealer and can only be described as exceptional in its service.  I had heard that some Flemings had gone to Cuba. Pat was nice enough to connect me with a Fleming owner who had made the trip on their own.  This was about two years ago.  He informed me that he had hired a lawyer who had charged about $2500 to assist in dealing with all the legalities.  The owner indicated that the lawyer was helpful in filling out the forms and guiding the way but that he certainly would not hire the lawyer again now that he knew the ropes. What he added was that Stuart, Florida seemed most friendly from a immigration and customs standpoint, and thus his strategy was to depart from and return to Stuart, Florida as opposed to Miami or Key West.  Thus, he added a fuel bladder to his boat to enable the required cruising range.  I did not view this as an attractive option, and this caused us to start exploring how to do it on our own.

The next step was to examine the twelve different exemptions from the prohibitions of Americans traveling to Cuba and select the best one for us.  I have been and am currently the Chairman of the Advisory Board to the Salvation Army in Alameda County. My theory was that I might work as a representative of the Salvation Army in evaluating how the Army could establish or extend its efforts in Cuba.  My investigations indicated that the Chairman of the Board for the Philadelphia Salvation Army had already successfully led a delegation from Philadelphia to Cuba.  I raised this topic with the Division Commander of the Salvation Army in Sacramento, and he delegated it to a Colonel in Phoenix who had just returned from Cuba.  I thought this might be a viable strategy with the idea we might take with us things like shovels, hammers, nails and other items that are in great demand in third world countries.  My concern was that the Army moves at a slow speed compared my usual pace of operation and could they move decision making on this front fast enough to fit with our time table?

About this time, my wife Melinda handed me a copy of Cruising World Magazine which was announcing a Cruising World / Harmony Charters sponsored rally from Key West to Havana.  While Harmony Yachts would be providing charter boats for the rally, they also would let other boats join for a fee of $1000 and would lead participants through all the paperwork.  Harmony had just successfully completed several cruises to Havana.  This would qualify for a non athletic people to people exemption.  After some extensive due diligence, we were one of the first of approximately 60 boats to join the rally.

Harmony provided us with the applications and identified the best exemption to apply under.  Cruising World, together with Harmony Yacht Charters coordinated with the commodore of the Marina Hemingway Yacht Club and arranged for us to participate in an historic parade of more than 60 yachts into Havana Harbor on the Sunday after arriving in Cuba. Additionally Harmony Yachts pulled together a number of tours for participants to partake in.  We filled out the necessary paperwork, obtained the Coast Guard permit and coordinated with our broker at Marsh to arrange for the insurance endorsement which extended coverage to Cuba.  We qualified for a people to people non athletic event.

During this time we invited a couple we have sailed with for years to join us.  Unfortunately subsequently they informed us that they would be unable to make the trip. We received this news while aboard the Fleming 65 Journey owned by Michael and Bobbe Brown last September.  Michael is also a member of the Cruising Club of America; we had joined them for a CCA cruise in the Pacific Northwest and had had a terrific time.  They were thrilled at the prospect of joining us for the adventure to Cuba.  We enjoyed cruising with the Browns not only because they are knowledgable and very nice people but also because they have Fleming 65 hull #15 whereas we have hull # 17.  Our boats are nearly identical, and both are well maintained.  Thus it makes cruising easy and enjoyable because we both know how the boats work, and we continually learn from each other's experiences with regard to the the nuances of these complex boats.  As Michael has said,  he is still learning his boat after more than ten years.  We still are learning our boat as well.

Log 2 of the  Cruise to Cuba Series provides the guidance and actual forms we received as we prepared for the trip.  We believe these would be very helpful to those considering a trip for themselves.

Peter Darbee
Captain/ Owner Sequoia