Gybing in Jamaica: A visit from the Jamaican Coastguard

Updated: Jun 17

I thought it was time I finally put this story to paper. It happened in February/ March 1986. I was just 20 years old at the time.


The story begins in St Thomas in the US Virgin Islands. I was tasked with delivering a Swan 46 to Galveston, Texas. A few months earlier I had met a young English guy in Antigua, who had just completed his first Atlantic crossing and we had hit it off immediately. I cannot remember how I got back in contact with him in those days, but anyway he turned up in St Thomas. [His name is Richard Merriweather and he remains a good mate to this day.] We did not have much cash so we decided to try to find a couple of crew, who might want a ride, in return for giving us some US dollars.


We found two young ladies who were keen to sail towards the USA; one was from somewhere in Oregon and the other, Los Angeles. I am sorry to say that I do not recall their names. They contributed towards supplies and I remember we bought beer with the money we got from them. In what was later to prove a significant moment, I sat them down before we departed and read them the riot act about drugs and not bringing anything on board. I thought they got the message, though at that time I cannot say I was 100% sure.

So off we went. It is a passage of around 1900 nautical miles that takes you underneath Puerto Rico Hispaniola and Cuba then across the Gulf of Mexico. Jamaica is enroute, so we figured we would stop there for provisioning, and Montego Bay sounded like a cool place.


Figure One. Rhumb line course from US Virgin Islands to Galveston


I remember a good trip downwind with the prevailing NE trade winds, swimming off the stern, enjoying the beers and having some funny conversations with our crew. The ladies were not very worldly. To their surprise, we were explaining that not every country used US dollars and we showed them some Australian dollars and coins. Looking at the image of Queen Elizabeth II on the coins, one announced they had no idea Australia also had a queen, just like the UK. The other, from Los Angeles, was amazed at all the stars in the sky and claimed to have never seen the stars before! (I guess partially due to the lights of LA being so bright.)


Figure Two. A rather young looking author enroute to Jamaica.



On the night before arrival into Montego Bay, we were sailing downwind on the northern side of Jamaica. Richard was on watch and he came below to stir me saying he could hear some large engines noise growing louder from astern. Ever aware to the possibility of pirate activity I jumped onto the VHF and put out a radio call identifying ourselves, giving a position, and asking the approaching vessel to identify themselves. I guess I thought at least someone else might hear of our plight and sound the alarm. After two calls with no answer and the massive engine noise growing ever louder but without any accompanying navigation lights or any light at all, suddenly the VHF sparked alive, “ This is the Jamaican Coast Guard we are about to board you!”. Well maybe it was the coast guard and maybe not. I responded, asking them to stand off while we dropped sails. The answer came back loud and clear. “Negative!, Heave-to immediately with the crew on the foredeck”.


I ran back on deck and grabbed the helm from Richard, just as a large spotlight flooded our yacht with light. The engines had backed off and the vessel was very close. I did not have my glasses on having just been awoken from sleep but through the glare I could just see a large vessel with a large gun (Bofers?) mounted on the foredeck and trained at us!


Luckily there was very little wind and Richard and the two girls stood on the foredeck. After a few minutes an inflatable boat approached our starboard side loaded with young Jamaicans wearing Mae West style life jackets and carrying sub-machine guns. The apparent leader, had only a knife in a pouch on his belt. I signalled Richard to come take the helm while I went below with the leader and one sub-machine gun man. I made the mistake of bolting below to get my glasses so I could see properly and was followed by the machine gunner who pointed his weapon at me till I showed him what I was grabbing. Oops.

The leader explained they were here to search for drugs and began going through the yacht picking up things and sniffing them. I asked how come they did not have a dog for that and he said he had been doing it for years and had a nose for it. Mmm.


Meanwhile, the girls were still on the foredeck and the blokes, still in their bright orange “Mae West” life jackets positioned themselves around the yacht sitting on winches or standing. Richard told me he made the mistake of reaching into his pocket for a smoke only to have multiple guns trained on him until he removed his hands, all the while remaining silent. One way to stop smoking!


Figure Three. An image of a similar Jamaican Coast Guard vessel. Two BIG guns visible.


We continued through the yacht with the smelling and searching. It seemed the boss man was relaxing a bit as he realised we did not have sail bags full of dope on board. Then, he moved to the bow and my heart sunk as I saw him pick up one of the girl’s backpacks then begin sniffing with intent. Oh shit I thought, here we go. Sure, he is looking for huge amounts but maybe he just needs a little find to justify his raid. He continued sniffing then conducted a thorough search of the back pack but found nothing, phew! The search concluded after about 40 minutes and I managed to convince him to sign the ships log as proof they had actually been on board. In discussion with the boss, after he had determined we were not drug smugglers, he explained that they targeted us because our zig-zag course as we gybed along the coast was taking us in an out of their 12 nm territorial region and so they assumed we were trying to keep out of their reach. The territorial sea is regarded as the sovereign territory of the country. Good to know!


Once they left, we got going again and I described what had happened below. I said to the girls that the lead guy had been very interested in one of their bags and has sniffed it a lot. “Oh”, she said (the one from Oregon) “ I had a big bag of dope in there but you told me no drugs, so I got rid of it before I came on board”. Turns out the pre-boarding talk was worthwhile! We continued toward Montego Bay arriving later that day. The story is nearly over, but not quite. We moored up stern-to in Montego Bay. and I set off down the dock to “clear in” with customs. As I walked along a rasta looking bloke signalled me and whispered, “Hey Maan, do you want to buy some ganja?” I laughed and politely declined. Then I saw something that will stay with me forever, a white guy walking along in his speedos (swimming shorts) with a handgun in a holster! WTF. Maybe Jamaica was not the best idea after all.

The visit to Jamaica concluded without further incident and we headed off towards Galveston with quite the story to tell!


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©2020 by Will Oxley.

Photo credits Amory Ross and John Grainger.