Photos by Mark Tozer, Wes Moses and Alan ‘Skanka’ Hottat

Editor’s note: Helen Wilson, Mark Tozer, Wes Moses and Alan ‘Skanka’ Hottat are one week into their attempt to be the first sea kayakers to circumnavigate the island of Jamaica. They will be checking in weekly on to post updates, photos and paddling advice from the field. Check back to see more, or visit their website:

Text by Helen Wilson

When setting off for an expedition in a place that you’ve never been, it’s easy to have predetermined thoughts of how that place will be. Before arriving in Jamaica, my thoughts were of warm, calm, tropical beaches with sunbathers and fancy hotels, and people drinking tropical beverages from hollowed-out coconuts. That is of course what you see if you Google “vacation in Jamaica.” But that is not the “true” Jamaica that my husband Mark and I have been getting to know over the past week with local sea kayaker Wes Moses and photographer Alan ‘Skanka’ Hottat (also local).

I am writing this from the patio outside the guest house where we’re staying. There’s a small shack selling beer and fresh fish to my left, green hillsides to my right and a raging ocean in front of me. The “breeze,” as Jamaican’s call it, is more like a strong wind, and it has been causing us problems since we arrived.

Our initial plan was to launch from Port Royal, located in southeast Jamaica, and paddle around the island counterclockwise. Eastern Jamaica is very exposed, and the swell and wind hitting that part of the island can be treacherous, so we figured we’d paddle it first and get it out of the way. Looking at the forecast though, we realized that the ocean had another idea for us. If we stuck to this plan, we’d be hitting the eastern point during the largest swell and wind days on the forecast. So we decided to launch from Great Bay instead, a protected area on the south coast. This way we’d paddle for a few days before going around the eastern point, and hopefully by then conditions would have calmed down a bit.

We arrived at Great Bay in the early afternoon on New Year’s Day. Our spirits were high, and we laughed as fascinated children examined all of our gear while locals asked us lots of questions. Most of them had never seen a kayak before, and they weren’t shy with their curiosity. With some playful children helping us get our kayaks to the water, we launched from the protected bay and rounding Great Pedro Bluff (a scenic bluff that, according to locals, has a cave with Taino paintings and ruins).

We headed east towards our destination knowing that we’d be paddling into a headwind for most of the afternoon. Coming out of the bay we were immediately hit with moderate winds, relatively large swell and lots of whitecaps. We were still making good progress, however, and estimated that if conditions and our speed remained the same, we’d be off the water in about three hours. Unfortunately, conditions did not remain the same. It wasn’t long before the swell size increased and whitewater replaced blue. Soon we were on a treadmill, going up one wave and dropping down the back of it, but not actually making any progress. After a few hours on this ocean treadmill, and the landing a good eight kilometers ahead of us, we had to make a judgement call: keep pushing through the increasing wind and deal with a tricky surf landing in the dark once we arrived, or turn around and surf the wind waves back to the start. There were no landing options in between. We opted for the latter, and were back at the launch–tired, hungry and frustrated–in under an hour.

As a group we decided to try to beat the wind the following morning, so we woke at 4 a.m. and made our way to the protected bay again. The small waves hitting the sand seemed more powerful than the day before, but we were determined. We launched in the dark, headlamps on our heads. We found it slightly eery as flying fish ran into the sides of our kayaks and our bodies, startling us. As we rounded Great Pedro Bluff, we were immediately hit with the strong wind that we’d paddled into the day before. It had blown all night, increasing in strength, and we knew that as the sun came up it would only get stronger, so defeated, we turned around and headed back to the bay.

Once again we needed another plan, so we headed to Long Bay on the northeast coast. We figured that instead of fighting against the wind, we’d paddle with it, putting in some miles the following day. Hopefully, by the time that we reached the south coast again, we wouldn’t be battling such a strong headwind. After a full day of driving we arrived at a perfect beach with the plan of setting out the next morning. The beach had a multi-layer surf zone, but the waves looked soft and gentle; the seas beyond looked calm and gorgeous. The next morning we woke to the howling of wind hitting the guest house that we were staying in, and a glance out the window made me cry, yes, literally cry, because the gorgeous surf zone had expanded to the rest of the sea, which was white and foamy.

A couple of deep breaths later, and after some Jamaican coffee with a breakfast of eggs and toast, we remain optimistic. We are on a gorgeous beach, looking out over a wild and unpredictable ocean, and we are learning. Jamaica is wild, unpredictable and downright wonderful. Whether this is a test for us, a lesson for us or something else, we’re going to go with it. Maybe tomorrow will be calm and beautiful, or maybe it will be wild and even more beautiful, but there are certainly worse places to sit and wait for the wind to quit and the sea to open up. Little by little or “Evrey mickle mek ah muckle” as the Jamaicans say…

–Read Helen Wilson’s ‘Guide to Painless Travel.’