Travel to Cuba, although uncommon these days, is not nearly as taboo as it was in 1999 when I sailed there with a group of friends from St. Augustine Florida. In those days, the US Embargo of Cuba was firmly in place, Fidel Castro was still in power and travel to the island nation was almost unheard of for Americans.
There was a traveling tourist attraction that used to stop over in St. Augustine in the late 90s. It was a replica of Christopher Columbus’ Niña. Supposedly the vessel was 99% period correct and accurate with even the nails used in construction being hand-forged.
The owner and captain of the ship was a fellow by the name of Morgan Sanger. That’s right, Captain Morgan. He was the son of Margaret Sanger, who was the founder of Planned Parenthood.
Captain Morgan took the Nina literally around the globe with his mostly volunteer crew, and gave tours of the ship to locals and tourists in each port.
In 1999 I briefly lived aboard a 38 foot sailboat named “Moonpie” that was berthed at the Conch House Marina in St. Augustine. I happened to be in the first slip, just inside the northern face dock, so, when the Niña arrived and set up shop, I was their nextdoor neighbor.
During the week the Niña was alongside, I got to know most of the crew and became friends, We’d play cards and drink rum together after their workday ended. I’ll clarify by saying I became friends with the “crew” of Niña. Captain
Morgan was very standoffish, to most everyone. I’d find out later that he wasn’t extremely popular with the crew either. In fact, his quarters on the boat were completely off-limits to anyone but himself.
Eventually we said our goodbyes and Niña left and headed north. When she landed in Brunswick Georgia a couple weeks later, one of the crew departed the ship, and I got a call. “Would I be interested in helping sail the Niña back south, from Brusnwick, to Florida. Titusville, Florida to be exact.
My dad, who was living close by at the time, drove me to Brunswick and dropped me off, and I boarded Niña as a mate.
It was quite an experience, but no pleasure cruise. Captain Morgan drove the crew pretty hard. There was always work to be done. Painting, repairing systems and appliances, meals to be prepared, cleaning. Morgan rarely spoke to anyone aside from his First Mate, Caesar. Caesar was a great young guy from Ecuador. He was NOT a volunteer crewman. This was Caesar’s full time job, and he took it very seriously.
Now, I’ve been sailing sloops all my life. At least since I was seven years old. I’m decent at it. But I have no clue how to sail a Niña. Caesar, as nice a fellow as he was, was responsible for the the sailing of this ship, and our timely passage to Titusville. He spoke very limited English and yelled at me for days in his broken dialect which I tried to understand. It was funny, but I didn’t dare laugh. I tried to understand and do as ordered. We made it to Titusville unscathed and on-time.
While aboard, I met a kindly gentleman from St. Petersburg who was retired and spending time as a volunteer crewman. I believe his name was Randy. He told me about an annual sailing regatta from St. Petersburg, Florida to Havaña, Cuba. The more I learned about it from Randy, the more I was determined to enter and go.
The simple explanation at the time was, that it was not illegal to GO to Cuba. It was illegal to spend US dollars in Cuba and break the embargo. So, for this particular event, the Cuban government dropped all entry and exit fees for the regatta participants, provided free overnight dockage, free fuel and electricity. Voila! No spending of US dollars!
After 9/11 all that changed and it became almost impossible to travel there, but in 1999, we went legally. Sort of.
To be truly legal you would stay in the marina or on board your boat, grill your own meals and enjoy your own rum and cigars. You think anyone actually did that?!?
OK…let’s back up to the beginning.
I’d been in St. Augustine a little less than a year at this particular time. My wife Karen and I had just barely started dating. I signed up for the Havaña Cup and invited local friends Dr. Rex and Mike, and an old Arkansas buddy, Dan. Last names have been redacted to protect the innocent.
Out of close to 100 regatta entries, we were one of only two from Northeast Florida. There was one other entry from Jacksonville.
My boat was a big, slow, Island Packet 38, so we entered in the spectator fleet and did not compete in the actual race. I calculated a 36 hour passage from St. Augustine to Fort Pierce, Florida, sailing south against, or inside the northerly flowing Gulf Stream. We planned to leave at 7pm, which would get us there in broad daylight.
I told everyone on our crew to take necessary precautions against seasickness if they were so inclined, to which everyone replied, “oh, dont worry about me, I’ve never been seasick.” We ended up leaving four hours late due to one of the crew having “woman issues”, and motor-sailed out the inconsistently lit St. Augustine inlet at almost 11pm.
The seas were rough. The tardy crewman, who had claimed he’d never been seasick, was green within fifteen minutes and chumming (vomiting) over the side. My second mate and I managed to sail the boat for the first several hours while the first mate tried to sleep it off.
There is a protected military zone off the coast of Cape Canaveral, so boats must sail many miles offshore to the east of the cape to round the necessary buoys before heading back west towards the coast. It was sporty. But Moonpie was a solid boat, and made the rounding without incident. In spite of the rough seas, the moon shined brightly above us.
We ended up tucking into the Cape Canaveral inlet the next morning and took a day of rest. I won’t say who the sick crewman was, but once we landed, he was able to call himself in a prescription for a transderm motion-sickness patch. The good-doctor was fine for the rest of the trip.
Over the next leg of the trip to Miami Beach we began to experience fuel related issues. Not sure if we had picked some bad diesel or the rough seas had kicked up some sludge from the tank, but we began fouling fuel filters. Yes, we were sailing, but in my years of traveling on sailboats, I've found the wind to almost always be blowing from where you want to go. Add to that a Gulfstream current working against you, and you realize that to get to your destination in any kind of a timely fashion, motor sailing is required.
So, sails were up, but the engine was also utilized. And we were low on replacement filters.
Miami Beach Marina was a great stop over to rest, re-fuel, eat a good meal at “Monty’s Dockside”, and plan the next leg of our trip. I believe Miami is where Dan flew in from Little Rock, Arkansas and met us for the remainder of the trip.
While there I bought a half-case of fuel filters thinking at some point, we would purge all the contaminants from the fuel. I would’ve bought more, but that’s all they had in stock.
Upon leaving Miami Beach and headed south, was my first trip sailing into the Florida Keys and it was magical. Up to that point, I had driven the Keys, down through Key Largo, Tavernier, Islamorada and Marathon, but the world is a different place when you’re on the water. That could never be more true than in the Florida Keys.
We sailed from Miami to Marathon on our first beautiful, yet uneventful day out of Miami. Outside of the Gulf Stream and with prevailing easterly winds, we were able to shut the engine off and enjoy some actual sailing, without the roar of the motor for a change. We spent a night in Marathon. Even some Floridians make the mistake of saying “Marathon Key”, which is inaccurate. Marathon is a city in the middle Keys and is made up of many Keys or islands starting with Long Key, the Conch Keys, Duck Key, Grassy Key and Boot Key. So, consider this story a geography lesson as well.
There are few places for a sailboat drawing five feet, with a fifty foot mainmast to stop over between Miami and Key West. Marathon is one of the best. Plenty of places nearby for supplies, good anchorages and marinas, and the Seven Mile Bridge, one of the only places to cross over from the Atlantic side to Florida Bay.
I know many folks have enjoyed the sunset at Mallory Square in Key West. It’s become one of Karen’s and my most favorite experiences over many years. To round the sea buoy on the south side of the island and arrive in town on your own boat however, under sail, for the first time, with sunset celebration in full swing is an almost indescribable experience. We passed the Western Union schooner full of joyful tourists, saw dive boats returning from the reefs, and were cheered by crowds onshore at Mallory Square. Dan pointed out a juggler performing on a tightrope to the delight of the crowd. Music filled the air.
We sailed past Wisteria (Christmas Tree) Island and dropped a hook at the anchorage. Someone had the idea of diving down on the anchor to make sure it was stuck, but with the current running through that area, there was no way. In fact, we were reluctant to take our dinghy to town in fear of the engine dying and us being washed out to sea. I’m used to 4 or 5 knots of tidal current on the bayfront of St. Augustine. I wouldn’t be surprised if it was ripping 7 knots here. Unbelievable.
I won’t spend much time here describing Key West. If you’ve seen it, you’ve seen it, if you haven't you should, and just know that a lot of the old, cool landmarks are gone. And the longer you wait, more of them will be, as it’s turning into a big corporate tourist trap. But, we still love it and recommend it to anyone who hasn’t been.
What we did do in Key West, however, was gain some knowledge about our upcoming passage to Cuba, both from locals who knew, and other regatta participants who’d done the race before. One of the more helpful and interesting things we learned was, to stock up on pencils, panty hose, bar soap, razors, tampons…simple things that we as Americans take for granted, and to hand them out upon arrival to the various bureaucrats that would board our boat when we arrived.
I don’t know if it sped up the clearing-in process, but the Customs people acted like we were giving them hundred dollar bills with these small gifts. It really hit home the scarcity of everyday items to the average Cuban.
Another thing we learned was the route from Key West to Havana, roughly 90 miles to the south.
Key West is blessed with a coral reef system that lies just to the south of the island and trails to the west almost to the Dry Tortugas. One must sail west several miles, to clear the reefs, before turning to the south. Our trip was to last approximately 19 hours from our anchorage. We left Key West at 3pm, May 26, 1999.
We sailed overnight and crossed the Florida Straits under a gloriously lit night sky. But, we continued to experience fuel filter issues. We had been instructed to hail the Cuban authorities via VHF radio so many miles out, prior to our arrival. Rex was the only sailor aboard who knew just enough Spanish to be dangerous. Naturally, as he attempted to hail Havana Coast Guard our VHF radio began to falter.
We made it into the harbor through some perilously looking markers that were probably rarely used by foreign recreational boaters. Scared to death that we would run aground, somehow we pulled Moonpie into Marina Hemingway and were instructed to tie up alongside a concrete bulkhead for clearance.
This is when the four-hour ordeal of clearing into Cuba began. Had we not had the gifts of tampons and pencils, perhaps it would have taken longer. Our CD player was confiscated, as was our GPS, to be returned upon our departure of course. The bureaucrats were friendly. Glad to have us in their country and full of questions. Just doing their jobs. What was maddening was the slow pace of their work peppered with frequent smoke breaks.
When we had completed check-in, we were directed to a concrete seawall to tie up. This was not your typical marina. There were no floating docks or piers, or power stations. In fact, when we tied up, a young man told us to throw our power cord out onto the grass, and someone would be by to help us shortly. When the next fellow arrived, he dug into the ground and pulled an electrical cable out of the dirt, cut it, and spliced it to the end of our power cord. When it would rain…which was every fifteen minutes, the cord would sizzle and smoke, but it never tripped.
There was a rumor going around the marina that due to a power shortage on the island we would not be able to run our air conditioners, and it was HOT. Africa hot. There were flies buzzing everywhere. Thankfully, that rumor turned out to be false.
There were 230 American flagged boats in Havana that weekend as along with the sailing regatta, the “47th Ernest Hemingway International Billfish Fishing Tournament” was also taking place. Things were quite festive. We quickly learned that local Cubans were not allowed into Marina Hemingway, It was for visiting boaters only. The Cubans you’d meet inside the compound were either government employees of the marina, or entertainers paid by the government to entertain the visiting yachtsmen.
Prior to embarking on this trip, I had made a visit to my home state of Arkansas to visit family and friends. I ran into an old character I’d known from growing up sailing on Greers Ferry Lake, by the name of Len Kempner. I mentioned this upcoming trip to Cuba and he immediately mentioned his friend Bob Asher to me (name changed to protect the innocent).
Bob was from Little Rock Arkansas, and was a friend of former Governor and then President, Bill Clinton. In fact, Bob operated a restaurant in Little Rock that Bill used to frequent. My friend told me that Bob was living in Cuba, and that we should contact him when we got there, and gave me Bob’s satellite phone number.
Well, we did contact Bob, and although he had no idea who we were, he was cordial as we apparently knew his friend who had directed us to him. Bob was a piece of work. Several big gold chains around his neck. He was living on a beautiful trawler at a nearby marina, with a new Z28 Camaro parked beside it. He also had a Harley Davidson look-alike motorcycle and a beautiful Cuban girlfriend. Bob told us that the lady had worked as a school teacher in Havana for $500 US per year. After driving her to and from work everyday for a few weeks, he said, “Hey honey, here’s three years salary, why don’t you just come hang out with me?”, and she did.
We didn’t know how Bob came to live in Cuba, or what his business was there, and we didn’t ask. But we liked him, and he was generous in his tips and offerings to us.
The best thing Bob did for us was to hook us up with a local driver he knew and send us to his favorite Paladar for dinner. Now understand that all businesses in Cuba are government owned and operated. Sadly, most of the restaurants are not good. A Paladar is an exception. In Cuba, Paladar exclusively refers to restaurants that are individually owned by Cuban people. This was an experiment in free enterprise by Castro and the Cuban government to certain privileged families.
We saw many exquisitely beautiful sites in Havana. But as our driver drove us to the Paladar, I saw some of the poorest squalor I’d ever seen. We were in what I’d call the inner city of old Havana. Our driver stopped in front of a tall gated entrance in the middle of what was nothing short of a slum. The door opened and we were greeted into the most beautiful tropical garden you could imagine.
It was totally obscured from the outside surroundings. And the Paladar, like Marina Hemingway, was off-limits for local Cubans. Only visitors were allowed inside the gates.
Our hosts were a gracious man and his wife and their wonderful children. I’ve forgotten their names but I remember the food. We enjoyed Cuban cocktails and beer and then dined on Arroz Con Pollo, Ropa Vieja and Lechon Asado. This was followed by a desert of Pastelito de Guayaba, made with guava paste and sweetened cream cheese inside a flaky puff pastry. And there was strong Cuban coffee. I don’t remember the price of the meal, I only remember being amazed by it. And the experience overall. I’d give anything to go there again.
We were in Havana for four days. We watched them hand roll and then we smoked Cuban cigars at the Partagas Factory where they had Havana Club rum on tap. We visited La Bodeguita Del Medio, the most famous bar in Cuba and the El Floridita, the birthplace of the Daquiri, where Ernest Hemingway supposedly hung out after moving from Key West in 1939.
One particular night, having become aware of how crazy the local Cubans were about most anything American, I decided to put on my Harley T-Shirt, jeans and biker boots to go out. (I lived on my boat at the time, so the stuff was aboard). In short order we were introduced to a local biker club where the guys were all riding vintage American bikes. Much like the old cars you’ll see there, the old Harleys are there too.
That same evening in a local night spot, we met some ladies. It seemed ladies outnumbered the men 3 to1 in Havana. But we met these girls and they wanted to dance. By the way, music is everywhere in Cuba and it is infectious.
I always considered myself to be a good dancer. I have rhythm. But the average white man’s dance step in America is slightly different than Cuban salsa. Especially when said white-man is wering heavy biker boots. I thought I was doing quite well however, when my lady friend began giggling and saying something in spanish to me. When I asked Dr. Rex to translate he laughed and said, “She’s saying you have feet of Stone!”
We walked the Malecon, the seawall that stretches for miles along the northern Cuban Coast, sat in with a couple local bands. One even played a rousing version of Hotel California in our honor. Sadly, we were not allowed to leave our mooring at Marina Hemingway during our stay, so we were not able to explore the coastline by boat while there.
All of us developed a deep sense of respect for the Cuban people. In spite of their economic situation, they seemed happy, were well educated and proud. If there is, or was, any sense of animosity between the Cubans and Americans, I’d opine that it stopped at our respective governments. The local Cuban people were some of the most generous and gracious I’ve ever met.
We found Cuba, or Havana at least, to be clean and friendly, in spite of its disrepair and deterioration. In the poorest areas, we never felt unsafe. Perhaps we were young and naive, but at that time I’d been to Mexico and other places in the Caribbean, and at home, that I could not make the same statement about.
When it was time to leave, the same four-hour process ensued, this time checking out of the country. Our confiscated belongings were returned and finally it was time to go.
Unfortunately when we were finally cleared, the weather was beginning to kick up. But, rather than wait and repeat the four-hour process again the next day, we cautiously left Marina Hemingway and were escorted out to see.
Did I mention that we had been having fuel filter issues?
The wind was mostly calm that night, but the seas were rough. We motored across the Florida Straits in darkness with an old school Garmin gps and a paper chart to show our way home. Then the engine would stall.
It was my boat, my responsibility to change the fuel filter, which required one to hang almost upside down in a hot engine compartment in rolling seas. Oh, and there was the smell of diesel. I’ve never been seasick in my life, but figured if it was ever going to happen, that would've been the night.
The fuel situation got worse. It seemed that every 30 minutes or so, the filters would clog and the motor would stall. I'm ashamed to admit that when we got down to our last remaining filter of the case I’d bought in Miami, I made the decision to dump some of the dirty fuel overboard and replace with clean, spare fuel we had in jerry jugs. We limped into Government Cut in Miami worried sick that the engine would quit at any time. After we landed, I hired a fuel polishing company to come to the boat, pump all the fuel out of the tanks, filter it and then pump in back aboard. We never had another problem.
Even though we had proper documentation, and had by all appearances completed our journey legally, we were still cautious. Many fellow boaters had advised that we clear back into the US in Miami vs Key West for various reasons nonetheless the overzealous authorities down there that might not be up to date on the “legality” of this semi-annual event.
1999 was before the proliferation of cell phones. The law required that the captain of a returning vessel fly a yellow, “quarantine” flag from her shrouds until the boat had cleared US Customs and Immigration. No one was allowed to leave the vessel, except the captain who was required to go to the nearest pay phone, and call the proper authorities for clearance.
It was a bit intimidating.
I recall going through a series of questions with the woman on the phone. She gave me a number to write on my clearance form and mail into US Customs. No one even came out to the boat. We’d just sailed in from Cuba! “Is that all there is to it?” I asked. I’ll never forget her answer, “Well, perhaps”.
A few days later Moonpie sailed back through St. Augustine Inlet. I sold her not long after that, bought a house and moved back onto dry land. Karen and I married and we bought a smaller boat some time later. One better suited for the weekend type sailing most of us typically do if we are still working. But that Cuban adventure still rates as one of the most memorable experiences of my life.
Thank you Captain Morgan.