May, 1977

Sailed out of Port Antonio towards Montego Bay and the emerging financial hub of Georgetown in the Cayman Islands. Rough passage up the Yucatan Channel and picked up the Gulf Stream. Pulled into Key West seven months to the day from when I set out.

May, 1977. An exhilarating 1000 nautical mile run from Port Antonio to Key West via the Cayman Islands. Rough passage through the treacherous Yucatan Channel. Arrived in Key West on 10 May, almost exactly seven months from when I set out.

1 – 10 May: Cayman Islands and Yucatan Channel to Key West: The powerful Cummins diesel hummed as we motored out of Port Antonio. We cruised west along Jamaica’s rugged northern coast, rocky headlands, thick jungles, flowing rivers and the odd fishing village. The mountains rose steeply above, providing a verdent backdrop to the landscape. Not unlike the terrain around La Cieba in Honduras, about 1000 kms SSW from Jamaica.

My glowing report of Montego Bay prompted Jim to layover for a day. We anchored off the beach and resort strip. I hung out while the Jim, Jerry and Brian rowed into town. Huge contrast to Port Antonio, many more tourists and fancy hotels. Lots of development. Gorgeous white sand beach, however.

Quick run up to the Cayman Islands. Sailed over the Cayman Trench, the deepest trough in the Caribbean, more than 7500 metres below. I’d read ‘Far Tortuga’ by Peter Matthiessen and was expecting a sleepy little island with a few fishermen and boaties, kind of like a mini-Roatan.

We motored in from the north to take a berth at the Cayman Yacht Club on the sheltered North Sound. The water was crystal clear. I was keeping bow watch as we slowly rounded the point and ran cautiously towards the Yacht Club in the distance. I saw a giant coral head dead ahead, we were almost on top of it! Yelled for Jerry to stop, quick fast.

He jammed the throttle in reverse and we came to a halt. False alarm. The depth finder showed 60 ft. The sea water was so clear and the refraction so pronounced that the coral heads seemed to be all around us. But we were floating far above. The Cayman islands had by far the clearest water I’d ever seen. No surface water meant no run-off. Huge contrast to Cartagena Harbor.

Sleepy little island? Not. Georgetown was full of flash hotels and restaurants, shiny office buildings, private jets flying in and out of the modern airport. Well-dressed locals and business types. Didn’t see many tourists. What gives? What was driving all this development?

Crooks, as it turned out. The Caymans is fast becoming a haven for drug money-laundering, cash-handling, off-shore trusts, tax shelters, all sorts of shenanigans. The government has taken a ‘hands-off’ approach to finance laws and taxation. As result, the Caymans are starting to rival Geneva as the destination of choice for ill-gotten loot. The locals are being priced out, replaced by slick banker types.

But the diving just off shore was fantastic and Jim didn’t mind paying the exorbitant dock fees. We ate well, explored the reef and marvelled at all the fancy new buildings. Not your average Caribbean backwater by any means.

After a few days of R and R we made ready for the final leg of the journey. It would be a 1000 nautical mile run northwest to the Yucatan Channel where we would catch the Gulf Stream. The fast current would push us up into the Straits of Florida and on to Key West.

It was the final leg of my journey as well. I’d been on the road (and sea) for almost seven months, hit nine countries, improved my Spanish and met dozens of really great people. Stayed totally stoned for the most part and enjoyed the charms of assorted young ladies.

Spent all of my money, $800. Worked out to a little more than $100 a month, $3.25 a day. Never went hungry, didn’t get robbed or sick, saw amazing sights. Sold or gave away almost everything I’d brought down. But I had a small collection of choice molas to sell and a quarter pound of primo Blue Mountain ganja in the  chain locker.

And now I was being whisked back to the very same place I started.

Sailing the Fantasy through the San Blas had been an adventure. The runs up to Jamaica and the Caymans were exhilarating. But the jaunt across the Yucatan Passage was a lot of hard work.

It was really just the three of us running the boat. Jim was getting tired and didn’t feel comfortable taking night watches. Two-hour shifts meant that none of us ever got enough sound sleep. The sails always needed trimming to catch the variable winds. We’d get knocked around by mixed up swells coming in from all directions, especially through the Passage itself. We missed Anne in the galley. And her ribald jokes.

After about five days we were smack dab in the middle of the Yucatan Channel. Cabo Catoche, on the Yucatan, lay 65 miles to the west. Cabo San Antonio, the westernmost point of Cuba, lay 65 miles to the east. Winds swirled. The channel was deep, 2800 metres, but the seas were choppy.

The Yucatan Channel is the main inflow of seawater into the Gulf of Mexico. As a result, there was a five or six knot current pushing us north, through the narrow strait. When the wind shifts to the north the chop picks up considerably.

The combo of swirling winds, short, steep and breaking swells and a speedy current meant that we had to stay alert at the helm. We’d fight the wheel, trim or let out the sails, watch for other boats. It was a busy shipping lane, not to mention fishermen with almost non-existent running lights.

Then, at the most critical moment, at night in a howling gale-force wind, the main halyard, the line that we use to lower and raise the main sail, jumped out of the block at the very top of the mast and jammed. The sail was about halfway down the mast and we needed it lowered. We were being driven on our beam ends and dipping the rail. The main sail had to come down. And fast.

One of us would have to get hauled up to the very top of the mast, unjam the main halyard and slide it back into the block. If we couldn’t, we’d have to cut the halyard and lose the mainsail to the wind and sea. Jerry quickly rigged up the bosun chair and snapped it to the jib sheet.

The 40-foot mast was teetering back and forth like a giant metronome on speed. The spreaders dipped to 10 feet above the raging seas on port, then 10 feet above on starboard.

Since I was the lightest it made sense for me to go up. Jerry and Brian were a lot beefier than I and could haul me up and down fastest.

Strapped myself into the bosun chair, put a few tools in a pouch, tied myself loosely to the mast and held on. Jerry and Brian used the hand winch to pull me up, but it was slow going. The wind pressures on the jib halyard, the wildly rocking deck and slippery lines required all their strength. Even Jim lent a hand.

By the time I was closer to the top I was being flung violently back and forth. I could barely hold on with both hands and legs. I would have been thrown overboard for sure if I hadn’t been tied on. Slowly I inched my way up to the top. At the very pinnacle I tied myself tighter to the mast so I could use my hand tools. I had a small pinch bar, but the pressure was so great that I couldn’t even budge the jammed halyard. It was hopeless.

But as I sat there trying to figure out what to do I noticed that the halyard slacked off for a few seconds each time we rolled from one gunwale to the other. I saw my chance.

Waited a minute to get aligned with the rhythm of the movements. I’d have maybe ten seconds each cycle to pry the halyard loose, lift it to the block sheave and slip it back in. The first attempt and I almost got my fingers crushed. The second attempt I got closer. Jerry yelled ‘You’re coming down. We’ll cut the halyard. It’s too dangerous.”

“Not yet,” I cried.

Last chance. Timed it perfectly. The halyard slackened, I slipped the thick nylon line into the sheave. The main sail gave a huge shutter and started to luff. We had control again.

Brian and Jerry immediately lowered the main sail and steered into the wind. The Fantasy stabilised, crisis averted. They lowered me back down. I was fried, had to sit down. But what a ride.

Continued on under a reefed main through the passage and then picked up the Gulf Stream at dawn. We literally flew into the Straits of Florida. Steered north, keeping far away from the Cuban coast, until we saw signs of the Dry Tortugas and the Keys. Pushed the helm due west.

These were my home waters. Skirted the Marquesas Keys, over the watery grave of the Atocha. Passed Sand Key lighthouse, the spider-like iron tower standing proud.  Almost there.

Jim had radioed ahead and reserved a berth at Steadman’s boat yard on Stock Island, Key West’s center for boatbuilding, repairs and industrial marine operations. I’d worked at the neighboring Munroe Boat Yard two years ago helping build fiber-glass lobster boats – nasty job – but learned a lot of practical boat building skills.  

And I knew the best way to enter the harbor. It was a tricky approach with dog-legged channels, unforgiving coral banks and barnacle-encrusted piers here and there. Jerry gave me the helm.

The early morning light was perfect. The channel and obstacles stood out and we were able to pick our way through quickly and easily. Pulled up to the dock at Steadman’s Boat Yard. Ah, Key West.

But first things first. US Customs.

“Where have you been?”

“Mexico, Panama, Colombia, Jamaica,” Jim offered. Smuggling hotspots all.

“Anything to declare?”

“Three cases of fine Jamaican Rum,” says Jim. “Can I pay the duty now?” He knew the drill. Jim was no dummy.

Jim wrote the check, signed a few papers, flashed our passports and, Bingo! Back in the USA.

Spent the morning washing down the Fantasy and straightening up after the bumpy ride. Worked fast and efficiently. Besides, I needed to clean the chain locker….

Mission accomplished. Hitch-hiked to Hilton Haven, walked over to the empty lot out back and found Mark sanding away on his under-construction Cross 33 trimaran, just where I’d left him seven months earlier.

“Hi Phil. Nice to see ya again. Almost sunset, let’s go down to Mallory Square. Hey, weren’t you going to Mexico or something?”

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