I had been wanting to properly explore Portland for months. I had the list of places I wanted to see, but I also knew that Portland is the kind of parish that rewards you most when you go with someone who actually knows it — not just the main spots, but the stories behind them, the timing, the feel of the place. So I went looking for the right guide.
That is how I found Deeno Stevens of Yaad Unlocked Tours. I sent him my list of must-see places, and he sent back an itinerary that covered every single one of them. Right then, I knew I was in good hands.
He picked me up in Kingston, right on time, and from that first moment the whole day was seamless. Deeno is a son of Portland — born and raised — and the knowledge he brings to every stop is not something you can find on Google. It lives in him. He was punctual, professional, and genuinely fun to spend a day with. I am already planning my next trip with him, and I am recommending him enthusiastically to every person reading this.
Here is how our day unfolded — four stops, one stunning parish, and an experience that is still sitting with me.
Instagram: @yaad_unlocked_tours_
Our first stop was Fish Dunn Falls, tucked away in the peaceful community of Silver Hill. The moment we pulled up, I understood why people never stop talking about Portland. You walk in and you are immediately surrounded by the kind of thick, lush green that makes you exhale without even thinking about it.
The falls cascade gently over rocks into a deep, clear pool that is cool and absolutely perfect. Getting in feels less like swimming and more like stepping into a painting. There was no rushing. Deeno gave me time to just be there, to swim and breathe it all in. That is the thing about going with someone who truly knows a place — you do not feel like you are being pushed through a checklist. You feel like you are being hosted.
Fun Fact
The falls got their name from an old Portland saying — locals believed “fish done” or “fish cannot pass” the strong flow of water. The surrounding forest is also home to several endemic Jamaican birds, making it a quiet favorite among bird-watchers.
From Fish Dunn, we made our way to World Pool — and this is the stop where I need you to stop and pay full attention. World Pool is a natural swimming basin fed by mineral springs flowing directly from the Blue Mountains. The water is turquoise in a way that does not seem real until you are standing right in front of it. And there it is, sitting in the middle of Portland’s jungle like it’s nothing.
Deeno told me that locals have considered World Pool a sacred healing site for generations. The mineral-rich water has long been believed to have restorative properties. After floating in it for twenty minutes, I was not about to argue with that. There is something about the place that makes you feel genuinely restored.
Fun Fact
The color of the water actually changes throughout the day — from a deep turquoise in the morning to a bright, almost electric blue in the afternoon — as sunlight shifts and hits the limestone base at different angles beneath the pool.
After World Pool, we headed to Charles Town — and this is the stop I feel most strongly about. Every single person who visits Portland should make time for this. No exceptions.
Charles Town is one of Jamaica’s historic Maroon communities, and the moment you arrive, you feel the weight of what happened here. The history. The sacrifice. The absolute refusal to accept anything less than freedom. The Maroons lived under one banner — freedom or death — and spending time in Charles Town helps you understand, in a very real and personal way, exactly what that meant.
We walked through the Asafu Yard — the community’s gathering space — and the community museum, learning about the history, the politics, and the heroes who shaped one of the most remarkable resistance movements in Caribbean history. I ended up buying an Abeng from the Maroon Craft Store. An Abeng is a horn made from a cow’s horn that the Maroons used to communicate across the mountains during battle. Holding it in my hands was one of those moments where history stops being something you read about and becomes something you can actually feel.
I also watched traditional Maroon drumming and dancing in the Asafu Yard. The energy is infectious and the performances are not a show put on for tourists — these are living traditions, passed down through generations, being kept alive by the people of Charles Town right now. You are witnessing a culture that survived everything, and is still here.
Instagram: @charlestownmarooncouncil
Our final stop was Moore Town for the Nanny Falls Tour — another company owned by Deeno, named in honor of Queen Nanny herself, national heroine and legendary leader of the Windward Maroons. While there, I also had the chance to visit the monument dedicated to Nanny and the Moore Town Maroon Museum.
I had heard about Nanny Falls before, but nothing quite prepares you for actually being there. The surrounding terrain once served as a natural fortress for the Maroons, helping them defend their freedom during colonial times. Every rock face, every ridge, every winding path through those hills meant something. It kept people free.
There is a short hike before you reach the falls — green, beautiful, and absolutely worth every step. The water tumbles into a pool that locals believe has been spiritually significant for centuries. It is said that Queen Nanny herself used these falls as a place of renewal and strategy. So when you step into that water, you are not just taking a swim. You are standing in a place where one of the most powerful women this island has ever known once stood.
I stood there watching the water fall, thinking about everything that had to happen for this place to still exist. For these stories to still be told. For me to be swimming there, learning them. That feeling does not leave you easily.
Fun Fact
Locals believe the waters of Nanny Falls are spiritually cleansing. Queen Nanny is said to have used the falls as a place of renewal and strategic planning — making a swim here not just refreshing, but a step into living history.
Portland is not just a destination. It is an experience that stays with you long after you leave. Fish Dunn Falls. World Pool. Charles Town. Nanny Falls. Four stops, one day, and more than enough to completely change the way you think about this island.
If you are planning a Portland trip — and you absolutely should be — reach out to Yaad Unlocked Tours and let Deeno take care of the rest. Sometimes hiring a guide you have never met can feel like a gamble. This one is not. He is the real deal, and your Portland trip will be better for it.
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