August 2020: Jamaica and the Roots of Rastafarianism

Big Islands, Small Islands

When I think of the Caribbean, I often divide the countries into two categories: the big islands and the small islands. Typically, I prefer the smaller, less crowded islands like Dominica, but Jamaica is an exception. Despite its size and population, the island has managed to preserve a laid-back vibe, largely thanks to its strong reggae culture and deep Rastafarian roots.

The Iconic Rastafarian Image

Rastafarianism may be found throughout the Caribbean, but its heart and origin lie in Jamaica. Rasta men are perhaps the most iconic symbol of the island—recognizable by their long dreadlocks, flowing clothes, and relaxed presence. Hearing them speak, with their melodic, reggae-like cadence, feels like stepping into a Bob Marley song.

That said, while many Jamaican men adopt the appearance of Rastafarians, relatively few fully embrace the lifestyle. The true Rastafarian way is more than a look; it is a deeply spiritual practice.

Rastafarian Beliefs and Lifestyle

Rastafarianism is an offshoot of Christianity, shaped by scripture, African identity, and resistance to colonial oppression. For Rastas, smoking marijuana is more than recreation—it is a sacrament, ordained by the Bible itself. They often point to Genesis 1:11 as divine approval:

“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.”

Beyond marijuana, the Rastafarian lifestyle emphasizes a natural diet free of alcohol and processed foods, a devotion to peace and love, and a calm, spiritual outlook—the same spirit that gave birth to reggae music’s soothing rhythms.

Symbols of Faith

The dreadlocks themselves carry sacred meaning, representing the Lion of Judah in its struggle against Babylon (a metaphor for oppression and corruption). Rastas also believe that the biblical hero Samson wore dreadlocks, his strength tied to them.

Their vision of the Promised Land is in Ethiopia, which they call Zion. To them, Emperor Haile Selassie of Ethiopia—who famously visited Jamaica in the 1960s—is the reincarnation of Jesus, destined to return and lead his people out of Babylon and back to Zion.

Rasta Man

Grave of Peter Tosh who performed with Bob Marley

Fresh Ganja at Peter Tosh’s Grave

Adventure in Jamaica’s Wild Interior

In Jamaica, you never need to go far to find adventure. While the beaches and resorts may attract most visitors, the island’s interior tells a different story. Much of it remains wild, a rugged landscape of rainforests, limestone caves, and remote villages.

Among the most fascinating communities are the Maroons—descendants of runaway slaves who resisted British colonization and carved out a life deep in the forests. To this day, many still live off the land, preserving traditions that have survived for centuries.

Cockpit Country: Jamaica’s Wildest Place

One of the most untamed regions is Cockpit Country, home to the island’s largest remaining rainforest. The terrain is riddled with hundreds of limestone caves, many of them still unexplored. It is a mysterious, forbidding wilderness—part natural fortress, part cultural stronghold—that has long fascinated adventurers and anthropologists alike.

Returning to the Island

This trip marked my second visit to Jamaica. My first was back in 2005, when a few friends and I hired a car and driver to circle the island in just four days. We avoided the mass-tourism hotspots and instead sought out the country’s soul: Maroon country, the quiet charm of Port Antonio, and the laid-back shores of Treasure Beach. Those off-the-beaten-path experiences gave me a very different perspective on Jamaica, one that went far beyond the resorts.

2005:Reach Falls

2005:Cliff jumping Negril

Beaches South Jamaica

Treasure Beach

Blue Mountains

Blue lagoon

Returning During the Pandemic

Because I had enjoyed my 2005 trip so much, and since Jamaica was one of the few countries that reopened to tourists during the pandemic, I decided to return—this time with my friend Richard. Of course, the reopening came with restrictions.

The Covid Corridor

Tourists were required to remain within what was called the “Covid Corridor,” a loosely defined zone covering only the resort side of the main road along Jamaica’s northern coast. Officially, the interior—where the rainforests, caves, and Maroon communities lie—was off-limits.

But for me, the interior has always been the best part of Jamaica. Remote, sparsely populated, and full of wild landscapes, it felt unthinkable to stay confined to the tourist corridor. Fortunately, as in much of the world at the time, the Covid rules were loosely enforced, giving us some freedom to explore.

Flying in Style on my First Private Jet

Richard, who had the financial means, kindly invited me along on the trip, covering my transport, including a private jet flight and hotels in exchange for my planning skills. Sadly, my fiancée Paula couldn’t take time off work, and I felt a little guilty going without her—but this was my first time leaving the country since Covid, and also my first time flying private, so I couldn’t pass the experience up.

A Base for Exploration

From Montego Bay, we would drive east to Ocho Rios and stay at the Jamaica Inn, a historic British-era hotel with a colorful past. Winston Churchill once stayed here, as did Marilyn Monroe, and the inn still exudes its old-world charm. It would serve as our base, while by day we set out to explore the island’s off-the-beaten-path interior—Jamaica beyond the resorts.

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

Day 1: Stop in Miami

Our journey began with a short flight to Miami, where we arrived late and stayed overnight. The real excitement, however, would begin the following morning.

Day 2: First Time on a Private Jet

The next morning we boarded a Hawker 800XP private jet that Richard had chartered to Montego Bay. It was my first time flying private, and I couldn’t help but feel excited. The cabin had plush leather seats, plenty of legroom, and a soft hum that felt worlds apart from commercial travel. Snacks and drinks, including bottles of rum and beer, added to the indulgent atmosphere.

We had two young pilots, both working to build their flight hours in hopes of joining a major airline someday. With no flight attendant onboard, one of them even stepped back mid-flight to serve us coffee—a small but memorable touch.

Pandemic Travel Realities

While most commercial pilots were being furloughed during the pandemic, private jet pilots were busier than ever. The wealthy never stopped traveling, even as the world shut down, and private aviation thrived.

Our flight was smooth and quick, just one hour over the middle of Cuba before descending into Montego Bay. For me, it was surreal—a taste of luxury at a time when the rest of the world still felt grounded and uncertain.

Interior of hawker 800 XP jet

Arrival in Montego Bay

We landed in a section of Montego Bay airport reserved exclusively for private jets. Ours was the only arrival, which meant immigration was entirely ours—no lines, no chaos, just us and a handful of officials.

Covid-Era Interrogation

The focus was entirely on our Covid status. Technically, no test was required, but we had taken one anyway just to be safe. Even so, the officials ushered us into a small, stuffy room with no ventilation. We kept our masks on, but the three immigration officers—now shut in with us behind a closed door—wore none.

They peppered us with questions about our hotel, health, and itinerary. The encounter reminded me of past interrogations I’d experienced in places like Libya, Pakistan, or Syria, where entering the country always seemed to come with an extra layer of suspicion.

Signing the Papers

Eventually, they presented us with forms requiring our signatures, stating that we would remain quarantined in our hotel. I pointed out that the official immigration website didn’t list quarantine as a requirement. The officials nodded in agreement but shrugged, saying we still had to sign if we wanted entry. We signed without hesitation—knowing full well we had no intention of remaining confined—and were waved through.

To the Jamaica Inn

Outside, our driver was waiting. With immigration behind us, we loaded up and headed east along the coast to Ocho Rios, bound for the Jamaica Inn, our base for the days ahead.

The Jamaica Inn Experience

The Jamaica Inn had everything I love in a hotel: history, atmosphere, and intimacy. Its architecture still carried the elegance of a bygone era, and unlike the mega-resorts that dominate much of the island, it was small, quiet, and exclusive. Best of all, it sat directly on a pristine, reef-lined beach.

A Place of Legends

My bungalow faced the sea, with a shaded patio where I could sit and watch the waves roll in. Just across from me was the pool once enjoyed by Marilyn Monroe, and nearby stood the VIP bungalow where Winston Churchill famously spent months at a time—painting seascapes, smoking cigars, and sipping brandy in his chair overlooking the Caribbean.

Living the Caribbean Dream

I absolutely loved this place. When Richard and I weren’t out exploring the interior of Jamaica, I filled my days swimming laps in the warm ocean, lounging on my patio, and sipping rum and cokes. The atmosphere made me feel less like a tourist and more like a foreign dignitary on retreat in the old British Caribbean.

The pool where Marilyn Monroe often swam

Portraits of Movie Stars Adorned in the Hotel

Walk to Blue Hole Falls

Dunn’s River Falls: A Familiar but Different Scene

On our first afternoon, a boatman picked us up directly from the Jamaica Inn and ferried us to Dunn’s River Falls. It’s one of Jamaica’s most famous attractions, but not exactly my favorite. The place has the feel of an amusement park, built up for crowds.

Still, this visit was different from my earlier trip. I was relieved to see no cruise ship crowds this time. Instead, the falls were alive with Jamaicans themselves, families and groups of friends out enjoying the day. That became a theme throughout this trip—very few foreign tourists, but plenty of locals savoring their own island’s beauty.

Blue Hole Falls and the Spanish Bridge

By our third day, we traded the coast for the mountains outside Ocho Rios, where we visited two of Jamaica’s hidden gems: Blue Hole Falls and the Spanish Bridge. Both spots were stunning, tucked into the lush hills, their turquoise waters flowing beneath canopies of green.

What made them especially memorable wasn’t just the scenery, but the atmosphere. We shared the day with Jamaican locals swimming, lounging, and laughing. Reggae music played from portable speakers, Red Stripe beer bottles clinked, and the scent of ganja drifted through the air. It felt authentic, alive, and worlds apart from the typical tourist trail.

Exploring Blue Hole Falls

Admission to Blue Hole Falls comes with a local guide, and it’s well worth it. Our guide knew every hidden corner of the river, leading us to the best cliff-jumping spots and showing us how to climb upriver through the jungle to reach a series of waterfalls.

The further we went, the better it got. Each bend in the river revealed a new cascade spilling into a turquoise pool. At some of the larger pools, the guide pointed out perfect ledges for cliff diving—safe drops into deep, clear water that begged to be jumped into again and again.

It wasn’t just beautiful; it was exhilarating, the kind of place that feels alive with both adrenaline and natural beauty.

Blue Hole Falls

The Vibe at Blue Hole Falls

Blue Hole wasn’t just about waterfalls and cliff jumps—it was about the atmosphere. Jamaicans filled the area with life, blasting reggae music from portable speakers, barbecuing meat on makeshift grills, and swimming in the turquoise pools.

Surrounded by jungle, with pristine waterfalls cascading around us, the whole scene felt raw and authentic, far removed from the polished tourist feel of Dunn’s River Falls. For waterfall lovers, Blue Hole is a must-see—less crowded, more natural, and infinitely more enjoyable.

Spanish Bridge

The Spanish Bridge: A Legacy of the Past

Hidden in the hills outside Ocho Rios, the Spanish Bridge is a relic from the island’s colonial past. Draped in moss and vines, the stone bridge was built by the Spanish in the 1700s, long before the British took control of Jamaica. While the plantations they established have faded into history, this bridge remains as a quiet reminder of their presence.

An Emerald Swimming Hole

Today, the bridge arches over a dazzling emerald-green pool, one of the most beautiful bodies of water I’ve ever seen. The scene is pure Caribbean magic: cool, clear water surrounded by jungle, with the stone bridge standing watch above. Entry is free, and it feels worlds away from the curated tourist attractions along the coast.

Swimming here was spectacular. Some of the braver locals leapt 30 feet from the bridge into the pool below, while others swung in on a rope tied to a tree. I spent hours jumping from the rope swing myself, drifting with the current beneath the old stone arch, then swimming back up to do it again.

A Local Gathering Place

What made the Spanish Bridge even more special was the atmosphere. Locals swam, laughed, and enjoyed the day while reggae music played from portable speakers. The smell of jerk chicken drifted from makeshift grills, mixing with the scent of charcoal, while bottles of Red Stripe clinked in the shade.

It was one of my favorite places on the island—authentic, vibrant, and alive with Jamaican spirit. My only hope is that it remains off the radar of cruise ship excursions so it can keep its local charm.

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

A Night at Glistening Waters

One evening we drove a few hours to visit one of Jamaica’s most unique natural wonders: the bioluminescent lagoon known as Glistening Waters. There are only three places in the world where glowing plankton can be consistently seen, and Jamaica is one of them. On a moonless night—perfect conditions—we set out to experience it for ourselves.

Rum, Seafood, and a Rasta Captain

While waiting for our boat, we enjoyed fresh seafood and a few rum drinks at the dockside restaurant. Soon our captain arrived—a dreadlocked Rasta with an easy smile—ready to take us and a couple of Jamaican families into the lagoon.

Before we set off, everyone dutifully put on life jackets. I assumed this meant they were planning to swim, but when I asked, the entire boat laughed and scolded me. “Crazy!” one said. As it turned out, no one had any intention of entering the water. The jackets were only for safety, in case the boat capsized—in water so shallow you could stand in, as I would later discover.

Swimming in Liquid Light

As we motored out, the propeller wake shimmered with an otherworldly blue glow. For thirty minutes we glided deeper into the lagoon, surrounded by mangrove forests, until the captain finally cut the engine in the darkest spot.

Then came the invitation: “You can swim now.” Richard and I were the only ones brave—or foolish—enough to slide into the water. Instantly, our bodies shimmered as the plankton lit up with every movement. It was a magical feeling, swimming in warm, glowing waters, trailing light with every stroke.

I avoided touching the bottom, where a thick layer of gooey muck waited, and instead treaded water, mesmerized by the luminous sparks dancing around me. It was surreal, almost like floating in liquid stars.

Richard and I swimming in the Bio-Bay

Day 4: Into Cockpit Country

On Day 4, we reluctantly checked out of the Jamaica Inn and transferred to a new hotel in Montego Bay, closer to the airport where we would depart in a few days. Along the way, I had charted a more adventurous route—into Cockpit Country, a remote jungle interior where Jamaica’s largest intact old-growth forests conceal hundreds of unexplored limestone caves.

The History of Cockpit Country

This rugged landscape has long been a place of refuge and resistance. During colonial times, runaway slaves used these caves to hide from the British, and to this day, their descendants—the Maroons—still live in the region. Many continue to grow their own food and live simply, deeply tied to the land. Rastafarian communities are also scattered throughout the jungle, their homes modest but self-sufficient.

The remoteness, however, brings risks. Banditry is not unheard of, and illegal ganja farms dot the landscape, their operators wary of outsiders. Even our driver expressed concern, not only about bandits but also about running into police. Since we were technically outside the Covid Corridor, a roadside “fine” or bribe was a real possibility.

The Hunt for Windsor Caves

Our destination was Windsor Caves, a massive wild cave tucked deep in the mountains. I had only vague directions scraped from the internet, and GPS was useless in the thick jungle. The dirt road leading there was barely wide enough for bicycles, choked with vegetation as the forest closed in around us.

We passed through a village along the way—the same place where Usain Bolt, the fastest man alive, grew up. Beyond the village, the road became even rougher, until we reached a fork in the trail. According to a traveler’s account I had read, this was the spot where we might find an elderly Rasta named Dango, who guided visitors to the cave. But the shack where he was said to live was empty.

Meeting Our Guide

Unsure which trail to take, we searched nearby. One house resembled a small ranch, but no one answered when we knocked. At a second ramshackle house, missing part of its roof, we had better luck. A friendly golden retriever bounded out, eager to cover us in licks. Moments later, a smiling Rastafarian man with long dreadlocks emerged.

The man, who seemed to know the area well, happily offered to take us to the cave. He explained that he often went there to collect herbs and plants for medicinal purposes. Before setting out, he warned us of a danger inside: a bat fungus. His warning matched what I had read online—scientists who had recently studied the cave contracted histoplasmosis, a lung infection caused by inhaling fungal spores from bat droppings. The symptoms, eerily similar to Covid, could take a week to appear, and in severe cases the disease could even be deadly.

But of course, this was not enough to dissuade us. With our Rasta guide leading the way, we pressed on toward the cave.

Jungle Outside of Windsor Cave

foot long jungle millipede

Into the Depths of Windsor Cave

We followed our Rasta guide for nearly an hour along a muddy, slippery jungle path until we finally reached the entrance to Windsor Cave. It was little more than a jagged hole in the ground, just large enough to enter while standing upright. Armed with flashlights, we stepped inside.

The Stench of Decay

Immediately, the air grew heavy—hot, humid, and pungent with the unmistakable smell of bat guano. The Rasta’s loyal golden retriever trotted in after us, unfazed by the darkness. The beam of my flashlight revealed tiny dust particles hanging in the air, likely laced with the very spores of Histoplasmosis we had been warned about.

Navigating the Darkness

We crawled over jagged cave formations, careful not to slip or tumble into piles of guano, each step a balance between curiosity and risk. The deeper we went, the more claustrophobic it felt, the walls pressing in and the air growing thicker. The thought that we were probably breathing in something dangerous lingered in the back of my mind, but the thrill of exploration pushed us forward.

The Bat Chamber

After nearly an hour underground, we reached a vast chamber. Thousands of bats clung to the ceiling in eerie silence, their bodies packed so tightly they looked like a living carpet. We knew that if we went any farther, we would disturb them—and once startled, the air around us would erupt into chaos as thousands of bats took flight.

Not eager to be caught in that storm of wings, or risk a panicked bite, we chose to turn back. As we retraced our steps, I felt both relieved and exhilarated, knowing we had ventured deep into one of Jamaica’s wildest and least-seen places.

Windsor Cave

A Narrow Escape from Cockpit Country

While we explored Windsor Cave, our driver had stayed back with the vehicle to guard our packs. When we emerged from the jungle, sweaty and covered in mud, he looked uneasy. A few men on motorcycles had been circling, watching him, and he feared they were bandits.

We quickly thanked our Rasta guide, gave him a tip for leading us through the cave, and climbed into the car. The timing couldn’t have been worse—just as we pulled away, the motorcycles fell in behind us on the lonely dirt road.

The Chase

Windows rolled up and doors locked, we bumped along the rough track with the bikers tailing close behind. They didn’t appear to have guns, and I told myself that as long as the car didn’t break down, we would probably be fine. Still, the atmosphere in the vehicle was tense, every glance in the rearview mirror a reminder of how isolated we were.

Reaching Safety

The motorcycles shadowed us until we reached the next village, where they suddenly veered off in another direction. Only then did we breathe easy. By nightfall, we were back at our hotel in Montego Bay, exhausted but grateful the day’s adventure hadn’t taken a darker turn.

Day 5: Cliff Jumping in Negril

Our final full day in Jamaica took us west to Negril, where the coast is famous for its cliffs and laid-back beach bars. We joined the fun with some adrenaline-fueled cliff jumping—first launching ourselves from 40-foot cliffs straight into the Caribbean Sea.

Into the Blue (Again)

Later, we drove inland to try another kind of jump: leaping from a 30-foot ledge into a freshwater cave pool. To make things even more confusing, this spot was also called Blue Hole Cave—just one of many “blue” places in Jamaica. The plunge into the spring at the bottom of the cave was exhilarating, the cool water a sharp contrast to the salty ocean earlier in the day.

A Night in Negril

That evening, we checked into a five-star all-inclusive resort in Negril. It was the kind of place most travelers dream about: unlimited food and drinks, pools overlooking the sea, and every comfort you could imagine. But for me, it lacked the charm of the historic Jamaica Inn. Still, I couldn’t complain—Richard had generously handled the hotels while I took care of planning the trip.

Reflections on Jamaica

Jamaica was the first Caribbean country I ever visited, back in my early twenties, and at the time it felt wildly exotic. Decades later, despite mass tourism reshaping much of the island, it still holds a special charm. The mix of music, culture, history, and wild landscapes continues to amaze me, and this trip only deepened my appreciation for a place that never loses its magic.

Onward to the Next Adventure

After Negril, our paths diverged. Richard returned home, while I continued on to the Dominican Republic for the next leg of my journey: cave diving.