The Chronicles of Jimmy Boylan: From Marco Island to Cuba, and back again

Jimmy Boylan
Special to the Eagle

Editor’s note: On May 23, Correspondent Lance Shearer introduced you to Jimmy Boylan’s next adventure, sailing his sloop “The Speakeasy” to Cuba. Boylan’s plan was to make a quick stop in Key West – “just a bump and run” – to pick up one more crew member, and then head out across the Gulfstream to Marina Hemingway in Cuba.

More:Havana day-dreaming: Marco Islanders set sail for Cuba

Boylan, along with a boat, a 1985 Endeavor sloop with 33 ft. overall (LOA) and 27 ft., 6 in. at the waterline, (LWL) is part owner of the Speakeasy restaurant on Marco Island.

Below is a follow-up to that report, from Boylan himself.

Also of note: On Friday, June 16, President Donald Trump, speaking from Miami, restored many of the travel limits to Cuba that had been lifted by the previous administration.

From left, John Gantz, Carol Cermak, Billy Hanson, Boe Cibula, Jimmy Boylan and Bobby Nash at a Key West pit stop.


Skipper Jimmy Boylan, age 63, owner of The Speakeasy of Marco Island, 10 years sailing experience.

Johnny Gantz, age 65, licensed 100-ton captain, many years sailing experience with several Atlantic crossings.

Billy Hanson, age 67, engineer and hand, many years sailing experience.

Patrick “Boe” Cibula, age 68, many years sailing experience, owner of “Docs Beach House.”

Bobby Nash, age 54 years, bartender at Quinn’s on the beach, Marriott Marco Island, deck hand and celestial navigator.

Capt. Jimmy Boylan, from left, Bobby Nash, Carol Cermak - who is not making the trip - and John Gantz. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner.


We originally planned to sail on Thursday, May 18, and spend two nights in Key West at Conch Harbor Marina. The plan was to meet Billy and Boe in Key West after a wedding they had attended and depart for Marina Hemingway on Sunday, May 21.

Weather quickly became an issue and nightly delays became a reality; 25-knot winds from the southeast across the Florida Bay would be intolerable and, as often happens in sailing, delays became the nightly decision.

We finally departed on Sunday, May 21, from Anglers Cove Marina at 1845 hrs. Billy joined us for this leg of the journey and we planned to pick up Boe in Key West.

With winds out of the southeast at 18 to 20 knots and four- to six-foot seas it was a pleasant sail. We travelled at five to six knots with the mainsail trimmed into the wind. The sky was a blanket of stars with a sliver of a moon.

We took turns resting, always leaving at least two on deck. We did not maintain a watch schedule but slept at will and kept two up top with no problem. Weather conditions wreaked havoc on Bob’s attempt at celestial navigation but we ended up arriving at Key West just 5.8 nautical miles west of the Northwest Channel, our goal.

We dropped the sails and motored into the very long channel into Key West. We arrived at Conch Harbor at 1545 hours. Boe Cibula joined us in Key West and we all enjoyed dinner at Pepe’s and a few drinks before retiring to bed early. Bob and I stayed on the boat, retiring before 11 p.m. and the others got rooms in town.

After breakfast we restocked the boat and sat down for a couple beers. We departed Conch Harbor at 1345 hours with a destination of Marina Hemingway. The wind was out of the southeast at 18 to 20 knots and seas were in the 5-7 foot range. It was a pleasant sail with warm breezes and no rain.

We did get a rare spray into the cockpit. We let out a lure, a “Tuna Treat” on the rod and reel that Wisconsin Jerry had given me for the trip. He had also provided the lure. At about 8 p.m. we caught a five or six pound Bonita. We got him off the hook and returned him to the sea.

Crew member Bob Nash practices with his sextant, for celestial navigation. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner.
Crew member Bob Nash with Speakeasy gear. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner.

Once again our navigation landed us approximately 20 nautical miles east of our destination but none of the crew complained. As the sun rose we found ourselves sailing west at seven knots passing the El Morro Castle guarding Havana Harbor and the downtown skyline! It was very beautiful and the sail was remarkable as we had a 25 knot wind directly out of the south while heading directly west – known in sailing as a beam reach! We were healed over and had the gunnels in the water – a great time! We arrived at Marina Hemingway at 1100 hours.

We had to check in with customs. A yellow quarantine flag is raised indicating that the boat and occupants have to undergo an interview and search process. Once the health inspectors determined that we carried nothing harmful and after taking our temperatures we were instructed to take down the quarantine flag and raise the Cuban flag. We then proceeded to Customs and Immigration.

The Cuban officials were very interested in any possession of guns, drones, bicycles and satellite phones. When it was determined that we possessed none of these items our passports were collected and we marched two at a time into the immigration office to be photographed and visas issued. We then proceeded to the harbor masters office at Marina Hemingway where I signed an agreement of payment and was advised of the charges.

With the exception of the young guardia who handled our immigration procedure, everyone we dealt with was happy to receive gifts of beers and 10 or 20 dollar bills. We sailed through the process in about one and one half hours.

Once checked in and after securing the vessel our drivers drove us to private residences, known as “Casa Particulars,” where we would stay during our time in Havana. Actually Marina Hemingway is located in Jaimanitas and our rooms were in Santa Fe, both just outside Havana. The rooms were nice and clean and air conditioned. The shower felt like heaven after a long nights sail!

Our drivers, Carlos and Nelson, both speak fluent English, have their own cars and are experts on the history and geography of Cuba. They are also great friends of ours and had made all of the arrangements for us. Marina Hemingway was waiting for us and had a slip reserved for us! It’s great to have friends in foreign places.

Boylan shows his Cuban courtesy flag, with a quarantine flag behind. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner.
Capt. Boylan below decks with gear yet to be stowed. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner. After a weather delay, Jimmy Boylan and his crew are on their way to Cuba aboard his sloop "Speakeasy," which shares its name with the restaurant of which he is part owner.

After showering the guys drove us to Santi’s, a small restaurant on the second floor of a dilapidated old building overlooking a dilapidated old harbor that had the best ceviche you have ever had! The octopus was just as tasty and, after devouring several portions of each, we were fully sated and ready for the yacht club.

Club Nautico, the Marina Hemingway Yacht Club, rests on the grounds of one of the most famous marinas in the world. They sponsor regattas, 22 this year at the time of our arrival, and fishing tournaments, with the Marina Hemingway Marlin Tournament starting on Tuesday.

Two of our crew were members and myself, Bobby and John joined the club on this trip. The yacht club is small but very comfortable with strong air conditioning, a fully stocked bar, big stuffed chairs and couches and a flat screen television, comforts rarely seen in Havana!

The bar has a single bartender and they never closed while we were in house! They were very accommodating! One evening I sat there all evening drinking rum and watching the Cubs, I stayed on the boat a short walk from the club that night!

Several days we had the guys drive us into Old Havana. Between personal observations of our crew and discussion with Carlos and Nelson, it was observed that the American influence is in Cuba. Prices have increased by 150 percent since the changes in U.S. policy. Rental cars that were $150 a day are now over $250 and none are available. The bars are now full of Americans, especially if a cruise ship is in town. There was actually a line formed to get pictures taken with the Earnest Hemingway statue in La Floridita, a bar that he frequented.

The old cars were beaters belching black kerosene smoke in years past. A taxi ride to the restaurant in a 1957 Chevy might cost $5-$8, now the cars are painted and restored, burning clean fuel and charging $50 an hour per person to ride on the Malecón! The Malecón is the Lake Shore Drive of Havana. It travels along the coast and can be closed when high waves swamp the roadway. At sun down people swarm to the walls and smoke cigars, enjoy a drink, or just look out to sea. It is a popular spot for lovers.

Havana is safe! If it is your first visit you will be surprised! Many Americans suffer the belief that the Cuban people dislike the American people – quite the opposite is true! The Cuban people can’t understand why more Americans don’t visit their country – well that is changing! Cuba is a police state, there are no guns. I am not saying that you cannot put yourself in harms way – just use common sense and stay to the beaten path and you will never feel threatened and there is no need for alarm.

One afternoon we had lunch at La Bodeguita del Medio, a famous Cuban bar and restaurant that was frequented by Errol Flynn, Earnes Hemingway, and the other rich and famous frequenting Old Havana. There are even Cuban songs about the place.

We were taken to a small room on the second floor. As we passed one room a band was playing and they were rocking, I was disappointed that we had to be in a different room.

Once seated mojitos were ordered and delivered promptly and they were mas fuerte (very strong)! We were then offered menus and basically just ordered an assortment of entrees with black beans and rice. The food proved to be delicious and the service was great.

There were three women at the table next to us – they were from Milwaukee, Baltimore and Washington, D.C. After they left a dozen young men came into the room – it was crowded! Then one of the band members told me they were coming to our room next – where would they set up?

The band entered the room and set up along a wall next to me. Another group of six entered the room and stood on the balcony. The music started and it was terrific. When they finished and exited the room Bobby told me that it was the most fun he had ever had in a small room with 28 guys and few chicks.

I purchased their CD before leaving the restaurant. We tried to purchase serving trays with the Bodeguita emblem but they would not sell them – America has not got them quite yet.

Everywhere you go in Havana music breaks out. Stop for a drink or a bite to eat and a band or wandering minstrels will be playing Guantanamera in short order! Give them a buck or two!

Back at the marina we learned that a large marlin had been caught by a young Canadian girl and had been half eaten by a shark – we went to investigate. We found the remains of what they estimated was a 250 lb. blue marlin. We took pictures and video of them cutting the fish into huge steaks for consumption. They related that while bringing in the fish it was bitten in half by a Cuban Night Shark. We googled it yes they exist.

We then returned to the yacht club for cocktails and two troubadour’s, one playing a guitar and one playing a fiddle, entertained us for the entire evening. Cuba Libre’s flowed and a good time was had by all.

We had been watching the weather and fisherman awaiting the tournament had been discussing the north winds that were expected on Tuesday. We did not need north winds and decided to leave Sunday afternoon under cover of nice east winds.

Carlos invited us for lunch and on Sunday we feasted on shrimp kabobs, pork, chicken and plantains. The balance of the food, enough to feed an army, was packaged up for our return trip. Upon returning to The Speakeasy I found that the food took up all of our refrigeration space and I promptly gave it to one of the marina guards. It would be a short overnight passage and juices and cocktails took priority. I would soon regret that decision!

We checked out at the marina paying our bill, shaking hands, giving away Cuban cigars, and some currency, to our hosts. We encountered the same young guardia that had checked us into the country and, after an hour or so we were underway, leaving Marina Hemingway at 1540 hours. Our destination – Key West!

The water drops off dramatically as soon as you depart the harbor and we had the sails up and were under sail minutes after departure. I tossed our lure into the water and let out about 200 feet of line and we were underway. To our dismay the wind was out of the northeast, our intended destination, so we sailed to the northwest and motored along. We could always change direction and motor into Key West as needed or, hopefully, the wind would shift.

About 45 minutes out of the marina our fishing reel began to sing as line was drawn out rapidly. Bobby was nearest the rod and began to set the hook and reel in our catch. It appeared that we had lost our fish as the line went limp – looking back we think he was swimming toward the boat. The reel sprung to life and went limp again and again. When we were convinced we had something on the line I put the engine in neutral and turned into the wind to slow down the vessel.

Bobby was feverishly manning the reel and reported that he could see the fish behind the boat. We all turned our attention to the stern and 30 to 50 feet astern saw a marlin jump from the water twice, the second time spitting out the lure and heading to open seas. We saw it clear as day – we all did – it had to be 6 feet or longer – a real beauty! John said, “Men doing manly things” as he and I sucked on Cohiba Behike cigars and high fives were exchanged. This made our day!

We continued motor sailing and our northwestern route was taking us off course but not a concern at that point. About three hours out of Marina Hemingway the alarm on the engine sounded indicating engine overheating. We immediately shut down the engine to cool it off. We had been healing hard to port in the northeast wind and I hoped that the water intake had been exposed to air causing the overheating – this was not to be!

I checked the sea strainer and it was relatively clean and water was flowing. It was now getting dark, in a bumpy ride, and it was insanely hot in the engine room, I decided to put off further repairs until daylight.

About 10 p.m. the fishing reel began to sing again – John and myself took turns reeling it in with similar results we had experienced earlier with the marlin. The final result was that the reel began singing and spinning and then popped loudly leaving no line on the reel – we can only imagine what sort of beast was on that line! I then turned in for some rest!

I had not quite fallen asleep when I heard Bobby stating that the wind had died and the motor needed to be started. I told them to let me check the belts and pumps first to not hazard further damage to the engine. My nap had ended!

Belts fine, strainer clear, it’s time to start taking things apart. The first hose I removed was the supply hose to the raw water sea pump. This is the pump that pumps cool seawater through the engine to cool it. No water was coming through the hose! Problem detected.

I examined the flow of the hoses and learned that the hose first feeds the ships refrigeration system and then the engine. I cut loose the refrigeration and installed a direct feed to the engine. Next I disassembled the raw water sea pump to examine the impellor. As expected it had been compromised and one blade was broken off and luckily wedged in the outlet of the pump housing – it had not gotten into the engine. Also I had stocked the vessel with replacement parts and had an impellor. I replaced it with Billy’s help.

It was now 3 a.m. and I was drenched in sweat – the engine room had to be 100 degrees and my shorts looked like they had just fished me out of the ocean. I was totally convinced that the problem had been corrected. With defiance I yelled, “Gentlemen start your engines!” and they did – within minutes the alarm sounded and I turned into bed dejected. I went to bed hoping that we could get close enough to Key West to summon Sea Tow and get hauled in for repairs.

When I awoke at 0700 hours I was informed that we were at a 60 degree heading holding five knots and heading directly into Key West – the wind had changed. Bobby Nash told me that he had been sleeping in the cockpit when he was awoken by the sound of a dolphin clearing his blowhole. Billy, at the helm, told him there were two dolphins next to the boat and they could almost be petted from the cockpit. The wind then changed directing us home. It is always believed that dolphins are good luck when accompanying a sailing vessel and this was no exception.

It was time for me to get back to the engine. I started at the top of the engine, at the heat exchanger – the first bolt I loosened resulted in a flow of sea water. I then removed the hose coming from the raw water pump and instructed the crew to start the engine – not so cocky this time. The pump was functioning and I reassembled everything. The engine ran smoothly and we were able to enter Key West under our own power.

We arrived at Conch Harbor at 1430 hours. We were welcomed By Carol Cermak who had arrived to join us for our last leg into Marco Island. Conch Harbor is connected with Dante’s a bar with a pool often full of hot young bodies and this day was no exception! Hot showers were the primary concern followed by dinner and an early bed time.

Breakfast was at Blue Heaven with filet eggs benedict and Bloody Mary’s and mimosas! I bought a hat and an extra impellor for the raw water sea pump and three bags of ice and we were off to Marco at 1550 hrs.

We experienced light southeast winds all night maintaining five- to six-knots with light seas and several cocktails – we deserved a quiet night. We actually slowed down intentionally to ensure that we arrived at daylight making landfall at 0700 hrs.

One of my crew members wife called us five geriatrics crossing the Florida Straights and wished us luck – I believe we got the luck! I am very glad I made this crossing but doubt if I will do it again. If I do I would insist on two or three days at Key West in both directions – back to back over night crossings take a toll on us geriatrics.