We were greeted in Port Bowden by a very welcoming Rastafarian. Kyle asked to take a picture and he obliged, but first wanted to pull out that straggling dread lock he had tucked into his beard.

Written by Kyle Hahn

April 5 – April 27: Jamaica

April 5th, 2016 we made landfall at Port Bowden. We stretched our legs on land and slept great in the well protected bay. Civilization was sparse around Port Bowden.  We saw various small farming operations and a few shacks along the rough road.  In the morning, we motorsailed 4 hours to Port Antonio where we reunited with our friend Dauphin and his parrot Baby Rico. He had departed from Panama and motorsailed straight to Jamaica. While we were peacefully sailing on one lovely tack from Colombia he had ran into heavy seas and strong winds. His passage was a wild ride with sea sickness, breaking waves, lines snapping, engine problems, and sleep deprivation.

While in Port Antonio we frequented the fruit and vegetable market and caught up with Dauphin and Rico.

The highlight of our time in Jamaica was renting a car, and driving through the Blue Mountains!  Our plan was to drive the narrow, winding road through the Blue Mountains, across the island to Kingston, and return via the more modern highway.  The road was a little rougher, windier, and more narrow than we had expected, but it made the challenge even more rewarding.  The road snaked through lush jungle, past waterfalls, many small villages, and coffee farms.  If we came upon another vehicle, we had to pull off the road, or often back up for a ways until we could find a spot in the road that was wide enough for 2 cars to pass.  To add to the difficulty of driving in the mountains, and even more so in the cities, Jamaica drives on the left side of the road.  Once we cleared the highest passes, we came upon “Holywell” which is a campground and park.  If we had brought a tent, we would have just stayed there for a day or two.  The air was fresh and clean, and the view over Kingston was spectacular.  We continued traversing down the mountain road, which became wider and smoother as we approached Kingston.

Once in Kingston, we stopped by a marine chandlery so Dauphin could purchase some more lines to replace the ones that broke during his passage, along with other various parts.  We drove through Trenchtown to see the neighborhood that Bob Marley came out of, and stopped by the Bob Marley museum.  We opted not to go in, as the day was getting late and the museum was expensive (~$25/person).  We made our way back to Port Antonio as it got dark, via a much quicker and safer highway.

After a couple of weeks in Jamaica, we were getting the boat, and ourselves, ready to continue north to the Bahamas.  We studied the expected wind and current patterns, to make our passage through the “Windward Passage” between Cuba and Haiti.  We couldn’t decide on whether we wanted to visit Cuba again by making a landfall on the south coast, in Santiago de Cuba.  Our route would take us nearby, so we decided that we would start sailing north, and make our decision based on our eastward progress and how we were feeling.

On departure day, we were first delayed in the morning by heavy rain, but decided that we still needed to depart if we were to make our safe predicted weather window.  We said our goodbyes to Dauphin and Rico, and started motoring out of the bay.  Just 4nm north of the coast, I noticed our engine temperature rising.  The exhaust was starting to smoke a bit, and we were checking different components, while the waves rocked us about.  We hailed Dauphin on the VHF, so he was aware of our situation and standing by for assistance.  The temperature continued to climb to 200 degrees F, which can cause serious damage to the engine.  I also found a fuel leak, spraying a fine mist of diesel into our bilge, so we immediately shut the engine down.  We decided it would be safest to return to Port Antonio under sail to make the engine diagnosis and repairs.  The entrance had a fairly strong cross current, rolly waves, and barely enough wind to make it back into the bay.  Dauphin came out in his dinghy, and we tied alongside so that his engine power could bring us in, and keep us off the rocks nearby.  We secured our boat on a mooring, and discussed our next plans of action as we dried ourselves out.  For the next few days, we ran tests to diagnose the problem, and eventually got things running smoothly.

Another week had passed before we had our engine running cooler, and we found a suitable weather window.  We probably did an equal amount of motorsailing and sailing, as we approached the south coast of Cuba.  When we got within a few miles of shore, we motorsailed east, with a slight countercurrent to help us along.  We adjusted our course to stay about 4-5 miles away from Guantanamo, to avoid any coast guard conflict.  We timed our approach to the eastern tip of Cuba, and the windward passage for first light.  As we snuck through, northbound, we saw huge ships passing by every 15 minutes, mostly southbound.  We were thankful that the weather was calm and the visibility was good with so much shipping traffic.  We were originally planning on making a landfall in Matthew Town, Bahamas, but continued northbound to Acklins, where we dropped anchor and rested on the west side of the island.  Our spot was safe, but not very protected.  We did not have a working depth sounder, so we used a small weight and line off of the bow as we approached shallow water and potential anchoring locations.  We knew this technique would be a little tricky in the shallow waters of the Bahamas.

That sums up our time in Jamaica. We’ve been back in the states for a while now, but we are determined to wrap up our blog so it tells the complete story from beginning to end.

Port Antonio


We were ecstatic to see our friend Dauphin and his parrot, Baby Rico, safely moored at the marina in Port Antonio.





Curried goat anyone?


This is the lighthouse that guides ships in and out of Port Antonio. We entered from the right in this photo (north), and then made a turn to starboard once clear of the small island.  When we had engine problems at sea, Dauphin met us just outside of this entrance in his dinghy to help guide us back in safely.  Sharp rocks! 




There are lots of push carts which vendors use, which reminds me of “Cool Runnings”



This unsuspecting restaurant off the side of the cliff is home to “Dickie’s Best Kept Secret”.



We enjoyed a four course vegetarian meal expertly prepared by Dickie. The British certainly left their mark on Dickie.


Our rental car, which took us through the Blue Mountains and across the island.


Passing by a waterfall in the Blue Mountains.





Holywell National Park and World Heritage Site.  I think we were feeling so happy to be there, we forgot to take many good photos in the park.


This is where we will pitch our tent the next time we visit.


I was struggling to reach the last flower on this tree. Kyle leaned out over the hill, pulled down the branch and waited patiently while I snapped a few photos.



EITS Cafe was an awesome find as we were driving through the Blue Mountains. They have several overnight rooms, their own farm that serves their restaurant and several more in Kingston and several dens to hangout. This place is away from the tourist traffic and beautiful.





Dauphin in front of the view from EITS cafe.


Bob Marley Museum in Kingston


We stopped at a pet store in Kingston to pick up a treat for Baby Rico. This character was all about Kyle.


We went swimming at Reach Falls for a few hours.  There is a path behind the falls that we climbed up to the pool at the top.


A guide took as up the river leading to the waterfall. On the way back down he showed us a path like an obstacle course. We swam, climbed and slid on the smooth rock where the water had worn it smooth. It was a 30 minute obstacle course all provided by nature.



Jamaica has several artists making wood carvings for sale. This artist carved a bust of “Nanny of the Maroons”. Legend is Nanny was an escaped slave who joined the native tribe of the Maroons and liberated other slaves and maintained freedom from British slave owners. There is still a community in Jamaica with descendants of the Maroons.


Goodbye Jamaica. Our next stop is the Bahamas.



  1. I see your selling the boat. Interested in purchasing the boat to continue adventuring aboard Winnie. Contact me if your still looking for a buyer.



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