Easy Trip to Key West

By David Sharp

We tend to forget how much GPS, accurate weather forecasting, and modern hull, sail, and communications technologies have improved our ability to get around faster and more safely on the ocean. Oh, and the wisdom that comes to most of us as we leave our 20s behind . . .

In 1974, Judy and I took a sabbatical from work for as long as our savings would last. We left our jobs in Dallas, sold most of our possessions, and began exploring Mexico by train and bus. We were staying on the beach (in hammocks under the palms) on the tiny island of Isla Mujeres when we heard of a young fellow named Troy who was looking for crew to help him sail a boat from Cozumel to Key West, Florida. I’d been sailing most of my life and, as our savings were getting thin, this sounded like a fun and inexpensive way to return to the States after our adventure.

As this was well before the age of cell phones, we made our way to Cozumel and started exploring Puerto de Abrigo, the only harbor on the island. There were only two boats from the US at the docks. The crew aboard one of them confirmed that Troy did exist and that his boat was the other, Honey. They confirmed Troy was looking for a crew, but added that he was now on the mainland, exploring the ruins. So, Judy and I started a daily routine of checking Honey and the incoming ferries, and on the tenth day Troy showed up.

Troy was also in his 20s, but younger than me and with curly blond hair, a beard, and a carefree attitude (this should have been a warning). He explained that his father was a retired airline pilot who had been living on Honey at Puerto de Abrigo for quite a while, but that he had returned to the States to dry out and had left Troy to get the boat home.

When we first inspected Honey she had various problems that included a broken bilge pump, no fuel, a non-working freshwater system, and a leaking prop-shaft packing gland. No marine supplies were available on the island, so we had to fix what we could with what we had. We stocked the galley and worked on the boat while taking many breaks to play cards, fish, and dive. After about a week of working on her, we decided Honey was seaworthy, and we took her out for a successful shakedown cruise (on a nice calm day). In hindsight, what we really should have been worrying about was how to navigate with only a compass and an RDF, but alas, our youthful optimism, lack of experience and growing investment in the trip cancelled out rational thinking.

Two of Troy’s friends, who had been touring Mexico, showed up while we were working on Honey. Troy had enlisted these two hippies as crew for the trip, but while we stayed in port waiting for a weather system to blow through, his friends decided they really didn’t want to go after all, and Troy’s crew became just the three of us. Troy and I were capable sailors, but we didn’t have a lot of offshore experience, and Judy was a good sport, but a real novice.

When the forecast seemed fair enough, money was short, and we were tired of waiting, so we told the Port Captain we were leaving. We got it all together and motored over to the town pier to clear customs, and there was no customs officer to be found. For 45 minutes we waited, while fending the boat off the stone pier with a swell rolling into the harbor. We couldn’t keep Honey from getting beat up, so we left, knowing we would never see this place again anyway.

As soon as we rounded the tip of the island, we were beating dead into big swells. Honey was a chubby center-cockpit ketch, a good old boat for living aboard, but not meant to go to weather. Motorsailing, we were making maybe 3 knots of headway. 

After we got the boat going and everything stowed, Troy took the first watch, and I tried to get some sleep in the aft stateroom. I lay there about 30 minutes before I was on my knees with my head in the head. When Troy called me for my watch, it took a superhuman effort to put my foul weather gear on and get up on deck, but once I started steering I was OK. The wind was about 20 knots out of the north, it was raining off and on, and we were taking tons of water on deck (it felt warm). By now the diesel was starting to get air in the fuel line regularly, so we would have to bleed it, and after a trip to the cramped, hot, smelly engine compartment, Troy was up in the cockpit with his head over the side. Judy (the novice sailor) was never seasick, but she couldn’t steer in these conditions, so she got Troy and me what little food we wanted. 

All the next dreary day it was an ugly scene. The crummy weather held, the rudder-shaft packing began to leak a lot, and the electric bilge pump quit, leaving us only the manual one. The weather then grew worse and the boat became a mess below from charts, tools, and wet clothes. The engine needed bleeding even more frequently, and we couldn’t find the air leak that was causing it to quit. Troy had vomited on the hot engine the night before and that pervasive smell wasn’t improving things. We had no autopilot, and by the second night, Troy and I were like rags, weak from seasickness and working the engine and the boat. To top it off, we were very unsure of our position because we couldn’t get an RDF fix. The signals from the few radio stations we could barely receive were just static-ridden Spanish. We’d seen no lights or signs of life since leaving and we had no way to communicate with the outside world.

That night, while I was on watch alone in the rain and pitch black, the only thing I could see was the white jib we had furled on the foredeck. As the boat fell off the tops of the big waves, the jib would lift and then fall back down. After hours of this I started to see the jib as a giant squid on the deck. Nothing I could do would dispel the image of the monster, and finally I ran below to wake Troy to show him the squid. He relieved me of the watch and we figured out that I was hallucinating from being tired and dehydrated. Drinking enough water turned the squid back into a jib.

Around that time, Troy bypassed one of the two fuel pumps and the engine stayed running, which gave us a great psychological lift. We fixed the bilge pump, straightened up the boat, and managed to keep some food down. We reduced the rate of the leak around the rudder shaft, the rain quit, and we saw a freighter. Just seeing the freighter and knowing we weren’t in some sort of twilight zone lifted our spirits.

But navigation was still a problem. I disagreed with Troy’s DR position when I finally looked at it. We decided there were only two places we could be and have come this far without sighting land. We were either southeast of Cuba, or northwest of Cuba. We sailed another day and finally sighted land at about 3 p.m. Troy at first hoped that by some miracle it was the Keys coming into sight, but the RDF said no, and when we saw that the land we’d sighted was mountainous, we knew it was Cuba and that we were south of it. We started sailing west along the southern coast of the island, intending to round Cuba’s west end and then head for the Keys. Just after sunset, we spotted a light ashore and decided it must be El Holandes near the tip of Cuba. I took over for my watch and Judy and I jibed the ketch back out to sea with everything set and later jibed her back to a course I thought would clear the tip of Cuba.

About two hours later, I gave the wheel to Troy and told him the course. But as soon as I hit my bunk it came to me that the light we had sighted might have been Maria la Gorda, well east of the one we thought it was, and that the northern course we were on would not clear the tip of Cuba after all. As I ran through the saloon to the chart table, I told Troy to jibe out to sea again while I replotted. Unfortunately, we couldn’t agree on which of the two possible lights we had sighted earlier, and there was no way to check as we sailed along the totally dark and featureless parkland coast of hostile Cuba. 

Deferring to Troy, we eventually returned to the course under the assumption we had seen the more western light, and I went back to sleep. About an hour later the boat heeled sharply and I went on deck to flogging sails and a very white helmsman. About a hundred yards aft was a reef with swells breaking over it. We were close enough to see the Cuban beach in the darkness and to hear the surf! We decided to head out to sea, and after gaining some room, we took everything down but a little jib and the mizzen and hove-to for the night. We were too tired to sail safely.

The next morning we got a good RDF fix showing we were finally near the western tip of Cuba, and we had to make a decision to turn to starboard and head for the Keys, or return to Mexico. After we took stock of how far we had to go into another norther that was coming through and acknowledging that we were running low on fuel and stores, we decided to head back to Puerto de Abrigo and take our chances with the customs officials. The sun finally came out and the 180-mile trip back was fast, downwind, and very pleasant. It always amazes me how quickly we forget ugly sailing experiences as soon as the weather turns nice.

We celebrated with a beer upon sighting Cozumel, but the party lasted only as long as it took the customs agent to find us. We said we’d just gone fishing, but he didn’t buy it (one fishing pole, no fish). We were accused of making a drug run to somewhere, and it cost us most of what we had left in cash to stay out of jail.

Troy wanted to restock Honey, make some repairs, and head off again for the Keys. But by now I was familiar with Honey’s shortcomings and with our inability to navigate. After a very short discussion, Judy and I decided that another try at Key West wasn’t a great idea. I called my father and asked him to wire me enough money for two airline tickets from Merida to New Orleans, which he did.

Troy decided to go back to the Mexican mainland to try to find his original crew with the intent of convincing them to take the “easy” sail to the Keys with him. He didn’t plan on telling them the whole story of how he ended up back in Puerto de Abrigo. Judy and I enrolled in graduate school and restarted our more conventional lives. As this was before Facebook, I never heard whether Troy and Honey made it safely back to the US.

After this ill-fated trip David got his masters in Ocean Engineering and has worked in that field ever since. After owning 18 boats, he and his partner, Nancy, now cruise New England waters from their homeport of Newport, Rhode Island, in Pegasus, the 1969 Tartan 34C David has owned for 20 years.


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