Jamaica-Beyond the All Inclusive Resorts to the Caves and Jungles of Cockpit Country

August 2020: I separate the countries of the Caribbean into big and small island countries. Typically, I prefer the less crowded small islands like Dominica but Jamaica even though it is a large island with a big population still maintains its laid-back island vibe with its strong reggae and Rastafarian scene. Rastafarianism, although found throughout the Caribbean has its roots in Jamaica. Rasta men are maybe the most iconic symbol of Jamaica, with their long dreadlocks, and a language of their own that sounds like something from a Bob Marley record. These laid-back dudes are a common sight across Jamaica. Although many Jamaican men take on the appearance of a Rastafarian, few truly practice the lifestyle. Rastafarianism is an offshoot of Christianity. The Rastafarian lifestyle consists of more than just smoking a lot of weed, although this is a big part of it. The Rastafarian’s believe that smoking marijuana is ordained by the bible and is a spiritual endeavor. They have taken the Genesis verse as follows to read that God is cool with smoking marijuana: Genesis 1:11 “And God said, Let the earth bring forth grass, the herb yielding seed, and the fruit tree yielding fruit after his kind, whose seed is in itself, upon the earth: and it was so.” They also strictly adhere to a natural diet without alcohol and promote a message of peace and love and a very chill vibe which is why we have the soothing tunes of reggae music. The dreadlocks are meant to represent the lion of Judah (Israel) in its fight against Babylon and they also believe that the biblical hero, Samson had similar dreadlocks. Rastas believe that the promise land is in Ethiopia, known to them as Zion, and that the black ex-emperor of Ethiopia, Haile Selassie, who once visited Jamaica 50 or so years ago, is the re-incarnation of Jesus and that he will return again someday to help lead his people to the promise land from Babylon.


Rasta Man

Grave of Peter Tosh who performed with Bob Marley

Also, in Jamaica you never need to go far to find adventure. Most of the island’s interior remains wild. The interior is a place of rainforests, caves and maroons-descendants of the run-sway slaves that still live off of the land. One of the wildest places in the interior is Cockpit Country. This is where the largest intact rainforest remains and hundreds of limestone caves, many still unexplored. 

This trip was my second one to Jamaica. My first trip was in 2005 when my friends and I hired a car/driver and drove around the entire island in 4 days visiting places that were not on the mass tourism route: maroon country, Port Antonio, and Treasure Beach.

2005:My friend Dan and I at Duns Rivers Falls

2005:Reach Falls

2005:Cliff jumping Negril

Beaches South Jamaica

Treasure Beach

Blue Mountains

Blue lagoon

Fresh Ganja at Peter Tosh’s Grave

Because I really enjoyed my 2005 trip and since Jamaica was one of the few countries that re-opened to tourists during the pandemic, I decided to return with my friend, Richard. This isn’t to say that Jamaica did not have any Covid restrictions in place. We were required to stay within what is called a Covid-Corridor which was loosely defined. The Covid Corridor only allowed tourist to remain on the resort side of the main road that hugged the northern coast. For me the best stuff was in the interior on the other side of the road, and I couldn’t accept that this area was off-limits, especially since this area was scarcely populated and would be easy to visit without interacting with people. Luckily, as is the case with most Covid travel requirements, they are loosely or not enforced.

On this trip, we would fly to Montego Bay via a private jet from Miami, and stay in the historical British Inn at Ocho Rios, where Winston Churchil and other celebrities like Marylon Monroe used to frequent. We would use the Jamaica Inn as our base to explore the off the beaten path destinations of the interior by day.


Map of Jamaica and the route I took on my 2020 trip outlined in yellow

Day 1/2: On day 1 we flew to Miami and arrived late, so we stayed one night. On the next morning, we flew in a Hawker 800 XP private jet Richard hired to Montego Bay. This was my first experience on a private jet, and I was pretty excited. We had 2 pilots and comfortable leather seats in the back. There were no flight attendants so one of the pilots served us coffee. The pilots were young guys accruing flight time to eventually gain enough flight time to work with the major airlines. While most airline pilots were being furloughed during the pandemic, private jet pilots were working like crazy.  The wealthy never stopped traveling when the rest of the world was grounded, and private jet pilots were busier than ever. Our flight was a quick-1 hour over the middle of Cuba to Jamaica.

Me in front of the hawker 800 XP jet  

Interior of hawker 800 XP jet

We were the only arrival in a special part of the Montego Bay airport reserved for private jets. This meant we had immigration all to ourselves. Immigration seemed primarily concerned with our Covid status. Even though technically a covid test wasn’t required, we took one anyways. Immigration summoned us to a small stuffy room without ventilation. While we were masked, the 3 immigration officials inside the room, now with the door closed, were not. they asked us all kinds of questions about our stay, hotel, health status. Our arrival into Jamaica was starting to remind me of similar interrogations I have has when arriving in places like Libya, Pakistan, Syria.

The officials made us sign a paper that stated we would remain quarantined in our hotel. I reminded them that the official Covid requirements on the immigration website didn’t require quarantine and the officials agreed with us but said that we still needed to sign the forms to enter the country. We signed the forms with no intention of quarantine and were admitted into the country. Our driver outside greeted us and transferred us to the Jamaica Inn.

Feeling Like a British Aristocrat at the Jamaica Inn

The Jamaica Inn has everything I love in a hotel; history, old atmospheric architecture, it is small and far from being a mega resort giving the feeling of being exclusive and it is quiet and located right on a beautiful reef lined beach. I stayed in my own bungalow with a patio facing the beach. Across from my bungalow was the pool that Marylin Monroe was knows to enjoy and a VIP bungalow that Winston Churchill used to spend months at in his chair facing the ocean painting, smoking cigars and drinking his brandy. 

I absolutely loved this place and when Richard and I weren’t exploring Jamaica, I spent my time swimming laps in the ocean, relaxing on my patio and drinking rum and cokes. I felt like a foreign dignitary in the British Caribbean. 

Me relaxing in the Patio of My Bungalow

Portraits of Movie Stars Adorned in the Hotel

Sightseeing Outside Ochos Rios

Walk to Blue Hole Falls

On our first afternoon, a boat man picked us up from our hotel and took us to Dunn’s River Falls. This isn’t my favorite place because of its popularity and amusement park like setting. I was happy to see a lack of cruise ship tourists unlike my previous visit. Instead of foreign visitors, Jamaican locals were out in force enjoying the falls. This was the case all throughout the trip; our trip, few foreign tourists and mostly locals out enjoying the sites.

3rd Day: On our 3rd day of the trip, we visited Blue Hole Falls and the Spanish Bridge which were located in the mountains outside of Ochos Rios. These are two incredible places that we shared with local Jamaicans listening to reggae music, drinking Red Striped and smoking ganja.

Blue Hole Falls

A local guide is included in the price of admission to Blue Hole Falls. The guide will show you all of the good cliff jumping spots into the falls and will guide you along the river up through the jungle to different waterfalls. The further you go upriver the better the falls will get. There are some great cliffs jumping spots into a deep pool of water.  

Blue Hole Falls

Jamaicans at Blue Hole played loud reggae music, and barbecued meat while swimming. Surrounded by the jungle in pristine waterfalls, this place is a must see for waterfall lovers and is much better and less touristy than Dunn’s River Falls.

Spanish Bridge

Spanish Bridge

The stone bridge draped in green from moss and vines, was built by the Spanish in the 1700’s. The Spanish, who were in Jamaica before the British also built plantations and the bridge remains as a legacy of the Spanish presence on the island. Today it stands over an emerald, green pool and is a favorite local swimming hole for Jamaicans. There is no cost to visit, and it is a safe and relaxing place to visit. This was one of my favorite places on the island and the emerald pool is some of the most beautiful water you could ever lay eyes on, and the swimming is spectacular. Some of the locals jump 30 feet off of the bridge or swing by rope swing into the river.  I jumped via the rope swing countless times and drifted beneath the old bridge with the river current and swam back up it. This is another fun place where I observed locals swimming, enjoying the day, playing reggae music, drinking Red Stripe beer and barbecuing jerk chicken. This spot shouldn’t be missed, but I do hope it isn’t discovered by the cruise ships so that it maintains its local charms.

Local Man Jumping into the River from a Rope Swing off the Bridge

Swimming in Bio-Luminescent Waters

At night we drove a few hours to visit a bay where the plankton become bio-luminescent when disturbed. It was moonless night, which was ideal for seeing the glow of the plankton, so we set off to visit Glistening Waters lagoon. This is one of three places in the world where you can find glowing plankton on a consistent basis. 

While waiting for out boat, we had a few rum drinks and ate fresh seafood. Then our Rasta captain came to retrieve us and a couple other local Jamaican families for our boat trip into the lagoon.  Before we set off all the Jamaicans on the boat put on life jackets. I asked if this meant they were going for a swim, and everyone chastised me as crazy. No one had any intention of entering the water and were only wearing life jackets in case our boat capsized in waters that were shallow enough to stand in I discovered later.

Our propeller wake glowed blue as we motored through the lagoon for 30 minutes into the lagoon before stopping in the darkest area, surrounded by mangrove forests. Then the captain urged everyone to go for a swim. Richard and I were the only ones that entered the water. It was a magical feeling to swim in the glowing warm waters. I tried to avoid standing in the bottom layer of gooey muck instead treading water.

Richard and I swimming in the Bio-Bay

Cockpit Country Caves

Day 4: On Day 4, we reluctantly checked out from the Jamaica Inn and transferred to a new hotel in Montego Bay, closer to the airport where would be departing from in a few days. Along the way, I had charted a route to a cave in Cockpit Country, a remote jungle interior where the largest intact old growth forests in Jamaica remain, concealing hundreds of unexplored limestone caves. many of the caves were used by run-away slaves to hide from the British during colonial times. To this day descendants of these slaves still live in the jungles in very modest homes and live very closely to the land growing most of what they need. There are also lots of Rastafarian communities. With the areas remoteness there is also the increased risk of banditry and running into illegal ganja farms that could pose risks.


Our goal was to get to Windsor caves, a huge wild cave that was located in the mountains down a dirt bicycle path sized road. I found very vague directions on the internet, and it was dubious if we would ever find the place, but we were up for the adventure of trying. Our driver was concerned about meeting bandits and the police, since we technically were outside of the Covid Corridor and could be subject to paying a bribe.

To get to the cave, we passed a village where the fastest man alive, Usain Bolt grew up. After the village the road became really overgrown and jungle denser. We were operating off of a string of hunches with no certainty of direction and GPS was worthless. Eventually we reached a fork in the road, where a shack described by a traveler who had been to the caves indicated we could find a n elderly Rasta man named Dango to take us into the caves. No one was around. There were numerous trials and we needed to choose wisely. In the distance we saw a few houses. One looked like a ranch house. We knocked and no one answered. Our second choice was a ramshackle house missing a roof. We approached it and a friendly golden retriever ran towards us to try and lick us to death. A Rastafarian man with dreadlocks and a big smile followed. The Rasta man was happy to show us the cave and said he goes there often to pick herbs and plants for medicinal purposes. he warned us of a bat fungus that he said was very dangerous. This matched what I read online from a cave science article on the cave. An expedition of scientists that came to the cave all became afflicted with the bat fungus, Histoplasmosis, which resembled the same symptoms as Covid and took a week to materialize. In some cases, without treatment and with a compromised immune symptom the disease could be deadly. This was clearly not enough to stop us from going further.


Jungle Outside of Windsor Cave

foot long jungle millipede

We walked for an hour through the jungle on a muddy and slippery path to the entrance of the cave, which was a hole barely big enough to walk standing upright through. They were prepared with our flashlights as we entered. it was hot and humid inside and the air was pungent with organic decay from bat guano. The Rasta man’s loyal dog followed us inside the cave. We crawled over cave formations, while trying not to fall down and injure ourselves or land in piles of bat guano almost guaranteed to have Histoplasmosis.   It was also likely that we were breathing it. The flashlight illuminated tiny dust particles suspended in the air. We hiked for an hour into the cave until we came to a room with thousands of bats roosting in the ceiling. From this point forward, if we continued, we would be guaranteed to send the bats into a panic flooding the air around us with bats. We decided to turn back to avoid disturbing them or accidentally getting bit in the crossfire.

Rasta man, who claimed to be an illegitimate son of Bob Marley, took us to  Windsor Cave

Windsor Cave

Our guide standing on a stalagmite 

Me in the cave with bats flying around my head 

Our driver stayed back with the vehicle to protect it and our packs. When we returned from the cave, he urged us to hurry into the car because of a few suspect looking guys on motorcycles that have been watching him. He was concerned they were bandits. We said goodbye to the Rasta man and paid him a tip for helping us and set off. At the same time, we set off, the bike gang started following us on the lonely dirt road. We rolled up the windows and locked the doors. They didn’t appear to have guns so as long as we didn’t break down, I figured we would be ok.  They continued to follow us until we reached the next village, where they took off in another direction. By nightfall we reached our hotel in Montego Bay. 


Day 5: On day 5, we visited the area around Negril and went cliff jumping from a bar and cliff jumping 30 feet into a spring at the bottom of a cave, called Blue Hole Cave. It is confusing in Jamaica with all the places with the color blue in their name. 

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