I didn’t even know where I was going 5 days before leaving. I didn’t even have a place to stay 48 hours before.
I didn’t know anything about Jamaica and just booked a flight to Montego Bay as a branch off point. I made a post on Reddit, asking people about relationships or recommendations there to visit… And got a bunch of wonderful replies. One of these, led me into a town in the mountains, having a day I will never forget, with a place that tourists never go. It was like I was the Pope visiting this small town.
I found a place on airBNB and reached out to them, and asked if they would like to trade for photographs. One of these is to be able to leave the locals with a place that attract more visitors, so they can make more money and live an easier life. But, the main reason is that, when I do a trade, I have to interact with the owner of the listing. I don’t just check-in, close my doors and connect to Wi-Fi. We have a long conversation when I arrive, and we almost always hit it off and become friends right away. Then, I see them everyday and many of them introduce me to family, or invite me to their homes for dinner. Or tell me special places to go, that only the locals know about. Or friends to visit in beautiful place. It always makes it a much richer experience.
Now, it’s like I’m staying at a friends house, rather than in a distant country where I don’t know anyone.
My first place in Jamaica was owned by a guy named Winston, that I know absolutely nothing about. When I arrived, he quickly greeted me and apologized - He would have to show me to my place quickly because he was in a meeting. I figured this experience my not be too special.
But the next day, he introduced me to his niece and her husband, and they asked me if I needed anything. I told them what I was doing there and they quickly offered to connect me with the tourism board. I said yes, please and I thanked them for the stay. Jennifer (the niece) told me a little about Winston and his story, which was absolutely awe-inspiring.
Jennifer took me to pick up my rental car, waited to make sure everything was okay, then drove in front of me as I learned how to drive in Jamaica (on the opposite of the road and opposite side of the car!). This helped a tremendous amount.
The next day, Jennifer told me Winston would like to have me up to his home for lunch in the mountains. I said I would love to go, and we all went up to an absolutely gorgeous home in one of the highest spots in Montego Bay, looking down over the entire city. Winston showed me around his property, where he had lived since the 60’s with his wife, even during some very tense moments in Jamaica. As we walked through his property, he showed me a different fruit tree every 5-6 feet and told me about the history and what they use it for. He told me stories about famous parties they’ve hosted there. He told me proudly about a wedding they had just had.
After the walk, he asked his wife to prepare a lunch for us all. I watched as she instinctually just walked through her property, where every tree and plant is burned into her memory, and brought back fruit and vegetables to cook. Winston went and got us rum to drink. We all sat and the conversation started flowing.
When he was younger, Winston a sailer. He would help other captains charter their boats and one day, he came back into Montego Bay and heard music playing at the Yacht Club. Him and the captain decided to go check it out and saw there was ska music playing, and lots of people dancing. Winston walked in, saw a beautiful girl he wanted to dance with and asked her partner if he could butt in. Begrudgingly, he let him and Winston danced so long with her that the partner eventually came up and said ‘If you’re going to keep dancing with her, you have to pay me back for her admission fee.’
He didn’t hesitate. He pulled the money out and gave it to the guy. This year, they will have been married for 45 years.
As a couple, they both have literally and figuratively fought vigilantly to keep Jamaica as great as it is. In the 70’s, under threat of communism, many Jamaicans fled the country out of fear. Winston recalls going to work on a Friday with some of his best friends and, on Monday, none of them showed up. They had all fled and didn’t say a word. Some of them he didn’t hear back from for years, since they were scared to tell anyone were they were.
Because he was involved in politics, many people advised Winston and his wife to flee the country also. He was getting death threats and they had to move him back and forth between his home and the mountains, to keep them both alive. He recalls having the paperwork for his Canadian visa sitting in front of him, where all he had to do was sign the papers, and he tore them up instead.
He said ‘If I die, I will go down with the Jamaican flag on my back.’
They never left and never will, he strongly says as we walk around his property, overlooking the city he helped build.
Since then, he has remained heavily involved into politics and make sure they stay a democracy. When drugs became a threat in the 90’s, he quickly had the government install checkpoints at each Parish, to stop the flow of trafficking before it got to the coast. He said ‘We will never become another Mexico.’ To this day, the checkpoints still exist.
Now in his 80’s, Winston is making sure Jamaica will be left in good hands when he is gone. He is helping build parks instead of businesses, in places where commercial endeavors would make a lot of money. In his legacy, this country will never forget the impact he has made.
