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A Boat Delivery to Florida via Cuba

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Papa Hemingway

Mike channels Papa Hemingway

The proposal struck a chord: Jock, an old sailing buddy, had his Pacific Seacraft 37, Annie, in Puerto Rico and welcomed hands to bring her back to Florida for sale. And since Cuba was opening up, Havana would be the intermediate destination.

Jock was a colleague from Foreign Service days. We had collaborated on Palestinian-Israeli issues in the late ‘70s and executed President George H.W. Bush’s strategy in the first Gulf War after Iraq invaded Kuwait in 1990. Upon retirement, I bought Panope, a Pacific Seacraft 34, and in 2011 Jock helped me sail her from the Bahamas to Bermuda and then on to the Azores. Inspired, he then bought Annie.

Age increasingly factored in. Jock, now over 70, equipped Annie for singlehanding—lines to the cockpit, mast pulpit, oversized winches, etc.—but found a human’s back more problematic than a boat’s rigging. On his passage from the Bahamas to the Dominican Republic in 2015, his back proved severely challenged during two long weeks of singlehanding against prevailing easterlies with the engine out of action. Multiple back operations later, and with the help of another friend, Mike, he had advanced Annie to Puerto Real in Puerto Rico.

Afterward, Jock reluctantly concluded that he should no longer singlehand a monohull offshore—working a well-heeled foredeck alone in a stormy seaway demands a younger man’s strength and athleticism. He pivoted to catamarans, bought a small Fountaine Pajot, but then needed to get Annie back to Florida for sale. He asked me and Mike to come along. We agreed.

Annie’s route

Annie’s route home via Cuba

We had many advantages as we contemplated the 1000-mile passage. Annie was a seaworthy boat that had been completely refitted in 2014 to Jock’s specifications at Pacific Seacraft’s facility in Washington, North Carolina. Jock, Mike (who also owns a Pacific Seacraft 34) and I brought with us more than a decade of blue-water sailing experience. Perhaps, most importantly, we could count in early November 2016 on prevailing easterlies and warm Caribbean weather. On the other side of the balance were our ages—Jock, 72, Mike, 64 and myself, 67.

In Puerto Rico, as we prepared for the passage, Mike suggested each of us write down any personal health issues and stow these notes in the first-aid kit. Jock’s back was obvious. Mike had slightly high blood pressure and blood sugar. I was prone to vasovagal syncope reactions. We all confessed to seasickness, for which Jock had been prescribed Phenergan while Mike and I let nature take its course.

Boat preparation included replacing a missing prop zinc, for which Jock donned a rented hookah, and refurling a spinnaker which Jock rigs on a custom bow sprit. Annie boasted a wealth of headsails: a spinnaker, a Code 0, a yankee jib and a furling staysail. The main could be triple reefed and on its third reef was meant to serve as a storm sail.

Jock tuned his SSB to Chris Parker for weather as we prepared to depart, but equally helpful was Mike’s Predictwind app, which provided reliable forecasts of both wind and sea state throughout the passage. Initially, we were looking at northeasterlies to take us through the Mona Passage and along the Dominican Republic (DR), then two days of light air before a cold front moved in from the North.

Our first day was fair sailing, but as usual, I had recourse more than once to a bucket or the lee rail of the cockpit. Jock and Mike fared better, but no one wanted dinner the first night. Jock had proposed three-hour watches that would naturally rotate as the days progressed so each watch-stander would have early, graveyard and late watches. On our Bermuda-Azores passage on Panope, we had been surprised in mid-morning on a beautiful sunny day by a ship looming over the cockpit. The lesson learned: someone needs to be standing watch day as well as night.

We made good progress under sail through the Mona Channel. However, a problem developed with the Simrad autopilot and neither it nor the Windpilot self-steering unit would hold course, so we hand-steered much of the time. It was a dubious prospect for a nine-day passage.

After coping with a nasty squall on the first night, we had some good sailing, broad-reaching at 6.5 knots before the wind dropped. Mike proposed that we make an unscheduled stop in Puerto Plata, Dominican Republic, to take a break and take on additional fuel. Still feeling punky, I welcomed the respite and the options additional fuel promised.

Since we were planning to stop in Cuba, Jock had previously filed a notice with the U.S. Coast Guard. Our permit stated no restrictions on intermediate stops, so we headed into the DR. Having first mistakenly entered the industrial port, we found in due course Ocean World Marina—the Disneyland of the Caribbean! A huge, garish casino loomed over the marina, and sea lions performed next door. Bedraggled, we contrasted with the clientele flocking to the slots, cigar bar and cabaret.

Annie at rest in moonlight in Marina Hemingway

Annie at rest in moonlight in Marina Hemingway

A quick weather check revealed that the light airs would disappear that night with the arrival of a cold front, then there would be clear sailing for many days ahead.

Once underway, Annie leaped through the sea on a broad reach under full main and jib. We were averaging about 6.5 kts., very close to hull speed. We had worked our way through the seasickness, and the crew polished off bean soup for dinner. Moreover, the Simrad system had recovered its basic point-and-go capability. As night approached, Jock reefed the main, and we weathered the 25-knot cold front handily.

As we made our way along Hispaniola and the Windward Passage, we fell into our sailing groove. With easterlies sometimes backing into northeasterlies, Annie sailed easily on beam and broad reaches, maintaining 6 knots. or better. Jock was active trimming the sails: rigging a whisker pole if the jib needed help, setting the Code 0 when winds diminished. He even deployed the spinnaker, but wind direction foiled its use. As I watched this 70-years-plus sailor, I concluded that, regardless of technology, a skipper needed the physical wherewithal to go forward and work sails, spars and lines. One cannot sail entirely from the cockpit.

Our nearly effortless progress allowed ample time and energy for debate. The utility of technology proved a favorite subject. I am a minimalist who rejects even refrigeration but has adopted AIS and satphones. Jock seems to embrace it all: SSB, radar, Iridium Go uplink, wind gauges, electric windlass, water maker and no less than four furling head sails. Mike took a midway position—heavy on electronics, less on hardware. 

Each could adduce evidence in support. Refrigeration meant our food kept well. We had ice on departure and on arrival nine days later. But we never used the radar because AIS provided us ample info on shipping in our path. In fact, the radar dome affixed to the mast proved a liability later in the passage when the main halyard fouled around it so badly that we had to tie it off and use a spare halyard to hoist the main. (Jock’s attempt to climb the mast while underway with harness and ascenders failed, but the halyard was easily freed in Marina Hemingway with a hoist by the crew. I suggested he remove the radar dome while he was at it!)

As we coasted along the eastern part of Cuba and threaded our way through the Old Bahama Channel, I took a night watch. Soon afterward a white light appeared off our starboard bow, but AIS showed no target. Gradually, it moved to our beam, and I could see running lights then flashing white lights. I summoned the skipper just in time for him to respond to the hail of USCG cutter 03, which had a few questions. Jock identified the vessel, himself, our ports of call and destination, and finally provided the number of the permit for our stop in Cuba. A very polite “coastie” took it all in, then wished us a pleasant voyage. Clearly, no vessel would be transiting between the Great Bahama Reef and Cuba without the USCG’s knowledge.

In a few days, we could make out the lights of Havana, and we timed our arrival at Marina Hemingway, just west of the capital, for early morning, motoring in with Nigel Calder’s guide as our reference. The modest blue building to our port housed the authorities. A doctor was first aboard to take our temperatures and confirm our health. Then customs, where my satphone was declared and put under seal—no telephone calls beyond Cuban government control! Finally, immigration where we were photographed and our passports stamped. Very modest facilities, but efficient one-stop processing.

Marina Hemingway is like no other in my experience: long, wide canals, some with condos allowing alongside mooring. Fees were modest. Facilities, like a shower, coffee bar and internet, were a short walk away. Rum and cigars were available at a Club Havana shop, basic supplies at the grocery. The four restaurants ranged from snack bars to a rather posh Chinese place. There was no free Wi-Fi, but one-hour cards could be bought for two convertible pesos (CUC), about $2. Later we learned that these Wi-Fi cards could become scarce as people hoarded them.

Our U.S. visiting permit specified our purpose as journalism, and we scheduled accordingly. Our subjects were: first, the USS Maine, the ill-fated Navy warship that exploded mysteriously in 1898 in Havana harbor, leading to the Spanish-American War in which Cuba became independent; second, Ernest Hemingway and his beloved fishing boat Pilar; and third, Cuban music.

Jock had contacted a fellow named Ricardo Hernandez to serve as a general fixer, and Rico showed up early the next day on his electric motorcycle, wearing a polo helmet as protection. Fast-talking with a ready smile, Rico promised to solve any problems and ensure we saw plenty related to the Maine, Hemingway and music. 

The following day he came back with our guide Haley, a delightful 27-year-old psychologist who had given up mental health for tourism, and Alberto and his ’57 cherry-red Pontiac, for which shock absorbers were a distant memory.

Havana delights in a helter-skelter way, and Papa’s tracks are easy to trace: from the Mondos Ambos Hotel where he lived between wives, to the Floridita Bar where his bronze statue appears ready to down a dozen Daiquiris, to the Finca Vigia where he entertained famous guests and humble fishermen and where Pilar rests in shining glory, to the little fishing town where he went to hear the local tales which he transmuted into The Old Man and the Sea and to our marina, where Papa presided over annual fishing tournaments and awarded a very young and triumphal Fidel Castro honorary trophies.

Our pilgrimage was remarked upon by the Cubans because in Mike we brought with us a Papa doppelgänger. With a smile, I took to introducing Mike as Hemingway’s great-grandson, Fidel! The Cubans were delighted. Their leader’s favorite gringo in the flesh!

Three days were too short for even our limited purposes, but the weather forecast had turned ominous. A strong cold front was setting in from the north with winds predicted in the 20-30 knot range. Our course for Key West was west of north to account for Gulf Stream current, but we were headed into harm’s way. 

So, we stowed our rum, cigars and guayabera shirts paid our bills and cleared out by midday. Winds were light and the sea calm as we drove north. Around midnight two USCG cutters hailed us and after taking our information, asked if we had been previously hailed. Yes, we confirmed, we were the same Annie USCG cutter 03 had checked on our way into Havana.

Getting a boost from the Gulf Stream, we made excellent time. At first light, we were at the approach to Key West channel and followed a couple of huge cruise boats through the reef and into Key West harbor. By now the winds were increasing, and the sea becoming choppy. Even in the lee of the key, we progressed with effort. Had we dallied and been in open water, the 90-mile hop from Havana to Key West would have been an uncomfortable passage, indeed! 

I had contacted Galleon Marina by sat phone to reserve our slip, and Cindy, one of the staff, was waiting as we approached. She cautioned us as we approached a shoal, then directed us to our slip. Age again intervened. From the bow, I relayed Cindy’s directions to Mike, who in turn relayed them to Jock. Without his hearing aids, Jock misunderstood and headed back out of the marina. We raised our voices to bring Jock around, but he perceived our efforts as alarm absent any danger and gruffly responded. The misunderstanding was immediately resolved, but demonstrated just one more challenge for aging sailors!

Eventually, though, we got turned around and lined up with the slip, where we docked smoothly. We laughed at the contretemps aspart of our general “lessons learned” exercise over a beer in a Key West bar. At the time, all that mattered was that Annie was back in the continental USA.

Edmund Hull was U.S. Ambassador to Yemen from 2001- 2004. He keeps his Pacific Seacraft 34, Panope, in Cyprus


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