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  • Writer's picturetheblacksprayhood

Upwind in the Western Caribbean and a Too-Brief Sojourn in Jamaica

Updated: Apr 2


"As we looked up, we saw the mast flexing forwards and back. The last thing we needed was to be dismasted..."



Sailing in the western Caribbean is certainly more challenging than the ultra benign conditions of the eastern side where you can day sail up and down the island chain, often with the wind on the beam. For us to get north east to Jamaica from Providencia would require several days of sailing directly into the wind. In addition we were trying to do it at the worst time of year (barring hurricane season) when the trade winds are at their most consistent and the long fetch could mean large seas.


You could wait for a few months for the wind to change and a few people in Providencia had been waiting. But we had a deadline to meet our friends in the Bahamas on 12th April, so we couldn’t hang about waiting for the wind to change.


We met a sailor from French Guiana who has been cruising since the 1990s, mostly in the Caribbean. We told him we were planning to head south east and then head north in order to reach Port Antonio in the northeast corner of Jamaica, where we could wait for the wind conditions to allow us to slip through the gap between Cuba and Jamaica to reach the Bahamas.


He told us the waves and conditions would be really strong and advised us instead to head north to Cuba and then head south to Jamaica. Whilst we would love to visit Cuba, we are trying to get our ten year visa to visit the United States and with Cuba on the terrorist list there since 2021, we didn’t want to jeopardise our chance of getting the visa.


There was also the Cayman Islands due north underneath Cuba. We’ve been trying to avoid the tax havens and private islands, but we saw that the tiny Cayman Brac would be the perfect stop to head north to and then from there head south east to Jamaica as there are no fees for visiting.


You can see from our track the tacks we had to make upwind

So we headed for Cayman Brac. We knew we’d have the wind on the nose until we got further north and our progress was painfully slow as we tacked. Eventually as we got north the wind angle was more favourable and we could make more direct progress to Cayman Brac. We arrived on a Sunday and picked up a mooring buoy. They are mandatory here to protect the coral and also free of charge.


Unfortunately when we arrived, we noticed that our baby stay was partially unravelled. Presumably partly a consequence of bashing the boat’s bow into waves upwind for several days. Still, the rig is only four years old so this was still a disappointment and we were aware we had much more upwind sailing to go to get to where it could be repaired.


An intrepid cat braves the outdoors, the strong breezes ruffling his fur

... And quickly decides to head back inside

The baby stay is the part of the rig that is attached at the front of the mast about halfway up and is attached at the bottom to a plate on the deck. Its function is to keep the centre of the mast from flexing and works in conjunction with two small side stays that all work on stabilising the centre of the mast, forming a triangle.


We cleared into Cayman Brac. It was probably the best entry of anywhere we’ve been. Entirely free and with the most friendly and environmentally aware customs and immigration officers we have ever met. They even told us that suncream is forbidden while swimming to protect the reefs. (We have a reef safe version). They only see about three or four sailing boats a week and most sailors don’t stay more than a couple of days and so they seem to enjoy visitors. We were the only sailing boat the three days we were there. Other people too were extremely helpful and friendly. 


Our lone boat in Cayman Brac

Unfortunately we couldn’t stay long. Luciano managed to improvise with some ropes and a block around the winch a way to pull the mast forward in a force acting as the babystay had and we hoped for the best as we set sail for Jamaica, heading first directly eastward towards Cuba and then South to Jamaica.


The improvised rope baby stay replacement

The mast seemed stable enough in the beginning with light winds. We drifted slowly past the gorgeous coastline of Cuba with its high cliffs with multiple caves carved into the sides and the Sierra Maestra mountains looming in the background. You could almost imagine the guerrillas hiding out to battle Batista’s forces back in the late 1950s. 


Then we tacked to head south to Jamaica with the wind hard on the nose and increasing in strength as we approached Jamaica’s coast. 


As we looked up, we saw the mast flexing forwards and back. The last thing we needed was to be dismasted. We moved off the wind and then decided to bring in the sails completely, motoring eastwards to Port Antonio along the coast without the pressure of the sails, riding the galloping waves up and down, up and down. The end of the journey seemed interminable as we fretted about the mast. At last we arrived a couple of hours after dark with the mast still intact.


Our first task was to try to find a solution for the rig. We still had more upwind sailing to do in order to reach the Bahamas in time to meet our friends. However, we were very concerned about our ability to find a solution to this in Jamaica, which does not have a large cruising community or many chandleries. However, we had to try.


As if to reinforce what can happen, a totally traumatised lone sailor was towed in the next day next to us. His mast had collapsed. All that was left was a hole in the deck. Somehow he had managed to cut it all away and had survived the terrifying experience. But that was it. He was done with sailing for good.


The dismasted catamaran, Port Antonio

We hired a car and with new pals Lea and Roland from s/v Victoria’s Ghost, we headed off to Kingston for our best hope at Durae’s Marine Supplies. As we drew up outside the tiny looking shop in a residential area, my heart sank. There was no way on earth this tiny little place would have rigging parts that would exactly fit our boat. Jamaica has fishing boats and visiting cruise ships, it is not on the mainstream sailing circuit.


Well all I can say is that appearances can be deceiving. We wandered around in awe at probably the best stocked chandlery we have been to in the whole of the Caribbean. Rooms led off rooms and staircases led to further piles of treasure. The owner has been amassing miscellaneous marine gear for decades. To top it all off, they have their own bar where you are given complimentary shots of rum to fortify your browsing stamina. More sailing boats ought to visit Jamaica for Durae’s shop alone.


After much hunting, we managed to dig out a part that if we could get it welded, would make it possible to fix our rig by reusing the same cable. But we didn’t want to waste our opportunity of being in Kingston, so we headed for the nearby Bob Marley Museum to make the most of it.


The museum is at the singer’s residence at 56 Hope Road, which he purchased in 1975. The tour guide was outstanding, with jokes galore. The property tells the tale of his musicianship, his commitment to Rastafarianism and heart stoppingly, it is also where he was caught in the crossfire of the political turmoil that racked Jamaica in the late 1970s.


Bob Marley's house in the background. Photo courtesy of Lea Oberman, S/v Victoria's Ghost

The evidence of his music abounds, from the first room which is covered in his award winning records to his personal recording studio and his ever-present guitar in his bedroom. 


His commitment to Rastafarianism is evident outside as well as in. Rastafarians have a deep reverence for nature and many conform to a vegan or Ital diet. Bob Marley wasn’t a vegan, but he did have a strong belief in eating natural foods and we were shown the kitchen where he used to prepare his unprocessed meals. 


The interior murals of Haile Salassie and the bedroom where his very last spliff lays unsmoked on his bedside table give further evidence of Marley’s religious commitments. In the grounds is a shop/café where you can buy cannabis and smoke it while playing his records. For Rastafarians, the smoking of marijuana enables a closer connection with Jah, or God.


In Jamaica smoking small amounts of marijuana in licensed premises is now legal for both medical and religious purposes.


In 1976 there was an attempt on Bob Marley’s life and the bullet holes where he was fired upon are embedded in the outside walls of his house. I first became aware of this assassination attempt through the fictionalised depiction of it in Marlon James’s A Brief History of Seven Killings. James became the first Jamaican winner of the Booker prize in this epic work told through multiple perspectives and it’s well worth a read.


Briefly put, Marley became a target through his involvement in the Smile Jamaica Concert in an effort to promote peace in the febrile atmosphere of the political situation in Jamaica at the time. Like many nations during the Cold War, Jamaica became caught in the crosshairs of the CIA. 


Whilst ostensibly neutral, many believed that Marley favoured the left-wing People’s National Party (PNP), led by Prime Minister Michael Manley. Manley had made positive comments about Fidel Castro and supported Cuba’s anti-imperial measures, such as sending troops in the Angolan Civil War. Alarmed by this, the CIA funded and armed the paramilitary wing of the right wing opposition party, the Jamaican Labour Party (JLP.)


It was JLP gunmen who shot Marley in the arm and chest and his wife, Rita in the head. Thankfully they and the other two victims who were hit, all survived. Two days later, Marley performed at the concert to a crowd of 80,000. But the attempt scared him enough to leave Jamaica and spend two years in exile in England. He continued to perform around the world before dying of cancer aged just 36 in 1981. He was given a state funeral in Jamaica and is buried near his birthplace in Nine Mile.


Jamaica's epic Blue Mountains

The following day, the four of us ascended the steep potholed winding roads into the Blue Mountains - home of the world famous Jamaican coffee plantations. We toured the family owned Devon’s Coffee Plantation. Devon himself introduced us to all the locally grown medicinal herbs, showed us the orange trees and the different stages of coffee roasting. Finally and most importantly we got to try his delicious coffee, home grown grapefruits and to buy some coffee liqueur and cannabis wine.


Devon talks us through the coffee production process. Photo courtesy of Lea Oberman, S/v Victoria's Ghost

The views were spectacular across the lush mountainsides. We had been warned to take a jumper to ward against the chill high up in the mountains. But the sun shone strongly and we sipped our coffees in the shade as Devon told us about how the plantations in the area were originally farmed by maroons. More recently, his grandfather had bought land and farmed food crops, like pumpkins. Gradually the plantations, large and small in the area, all switched to the more profitable coffee and it was Devon himself who had made this conversion on his land.


We drove on and stopped again for another coffee on a road side perched above the mountain side. A Streamertail (or Doctor Bird) hummingbird fed from a feeder and the café owner informed us that they are only found in Jamaica. The males have long tails and are really spectacularly elegant.


The next day it was back to the business of fixing the rig. The first task was to visit a local welder to see if he could weld in Stainless Steel for us. Luckily he could and Luciano was able to effect a temporary repair and reinforcing under the deck until we can get the rig professionally examined.


The unravelled babystay (before) and after welding


Before we set sail again we had the important task of stocking up on Jamaican delicacies. We had heard that our next stop, the Bahamas, is very expensive, so we went a bit crazy, going shopping three times! Here’s some examples of our shopping below, not including the fruits and vegetables. And a shoutout to Juici Patties in Port Antonio which has two flavours of vegan patties - soya and vegetable.


An array of Jamaican goodies

And so onwards to the Bahamas. This passage was partially upwind until it changed in our favour. The rig was marvellously strong. The deck less so, continuing to ‘breathe’ up and down. It will need a proper backing plate and reinforcement, but we are one step closer to meeting our friends. However, the Bahamas brings a whole new set of weather and navigational challenges that are totally different to elsewhere in the Caribbean. 


There's no video this week as we sadly lost our phone in Jamaica along with our footage :-(


You can find our PODCAST episodes at the links below

YOUTUBE (for video version)





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