Jamaican Road Trip

Sitting in the driver’s seat, a friend in the passenger seat, our luggage in the trunk. A long stretch of road is in front of me, the city is at my back and off at the horizon lay the Blue Mountains. I have the window down allowing a breeze in cooling down what would have otherwise been a sweltering hot day. We are excited, she perhaps even more so than I. We are ready for an adventure.


Road trips are the epitome of Americana. Ever since Jack Kerouac’s “On the Road” the American imagination has been fixated on the open road. The road trip symbolises possibility, adventure. Anything can happen, from comedic antics, to family bonding, to coming of age – as we have seen in the many films on the subject.  However, my road trip was not in America, my friend and I decided to take this quintessential piece of Americana to Jamaica.


This was not my first time to Jamaica, to say the least. A little known fact about me, I am a Jamaican citizen – but that is a story for another day. I have been back and forth to the country for nearing on 20 years now. I have owned vacation homes in Montego Bay and Boscobel since 2005. It’s safe to say that I know Jamaica quite well, the land, the people, the culture; I even pride myself in dabbling in a little patois.


However, no matter how many times I go back to Jamaica there is a sense of awe of the natural beauty, the richness of culture and color, and the diversity. I find myself “oohing” and “aahing” like a tourist all over again. So when my friend expressed interest in seeing Jamaica I was immediately on board, and excitedly suggested we make it a road trip, so I can share some of that sense of wonder with her.


Our trip began with our touchdown in Kingston, Jamaica’s capital and most populated city. Kingston is as a Caribbean capital should be: vibrant, loud, colourful, musical. Sandwiched between Jamaica’s Blue Mountain’s and one of the largest natural harbours in the world, this city will not only overwhelm you with its size, liveliness, crowds and awful traffic, it will also stun you with the beauty of its immediate surroundings.


Stepping off of the plane and letting the heat hit me, and it felt a bit of a coming home. It had been a while since I had the chance to get to Jamaica and I was eager to see what had changed and what stayed the same. After sorting our rental we hopped in to head to our hotel. The city is divided into two distinct halves, Uptown is the newer more affluent area, where the diplomatic class reside and the best restaurants and hotels are situated. Cosmopolitan, with panoramic views of the rest of the capital below, this is where our hotel was located.


The other half, Downtown Kingston is a stark contrast – a melange of historical Spanish and British colonial buildings, somewhat run-down, but all the more charming for it. At its western edge lies the ghetto of Trench Town, made famous by Jamaica’s biggest international celebrity Bob Marley. However, the warm, familial vibe that Marley described in the neighbourhood has been overshadowed in recent years by jarring poverty, thin rule of law, and the violence that descends from that. Many of the rusted, ramshackle tin roofed homes, crowded together don’t have running water.  Appropriately many of the districts are nicknamed to signify struggle and war: Jungle, Tel Aviv, and Dunkirk (after the famous battle in World War II) to name a few.



We weaved our way through the streets working our way up until we crossed Main St, the unofficial boundary separating Uptown from Downtown. We were to stay in Kingston for the first two nights of the trip. As we drove through the downtown streets I spotted the first thing that had changed since I was last in Jamaica… or rather I smelled it.


Marijuana, in small amounts, was decriminalised in Jamaica in April 2015. Possession of less than 2 ounces, or growing five or less plants is now perfectly legal. The country planted its first legal plant, approved for medical research purposes, not long after. The hope is to begin regulating the industry and allow government sanctioned distributors. Lawmakers, though going slowly and methodically, have been watching the tourism boom of Colorado and no doubt intend to capitalise on it in the tourism-driven country.


Though selling the drug unapproved is still illegal, the relax of the law was already evident with bushels of green crop on the back of scooters and a fragrant puff of smoke emitted from a car which pulled up beside us at a traffic light.  As apparently obvious tourists, on-the-side dealers approached us for sales throughout the entirety of our road trip. However, to be fair, a tourist being approached for weed in Jamaica is not new.



We spent a few nights in Kingston, taking in its contrasts, its sensuous nature, and its rowdy nightlife. However, Kingston wasn’t the main attraction of this trip and before long we were on the road with the Blue Mountains at our backs, on our way to Boscobel – Ochos Rios’ quieter neighbour.

A two-and-a-half hour drive, in the warm Caribbean sun – it was a must to stop along the way for an ice cold brew and some delicious local favourites. Roadside stalls are ubiquitous in Jamaica, but none so celebrated as the culinary corridor, Faith’s Pen, packed with stalls selling every native delicacy you can dream of.


Years ago when I first visited it, Faith’s Pen was right along the main highway and would be packed with persons waiting in line for Jamaica’s iconic dish Jerk Chicken, and the national brew Red Stripe. Now, with a new highway recently built, the location doesn’t enjoy the same traffic it once did. When we got there it was strange for me to see it so empty, we were amongst the only ones there. However, that didn’t dampen the spirits of the stall-owners, who cheerfully attempted to persuade us to choose their stall for lunch. We allowed our nose’s to make our choice, settling on a grill turning out jerk chicken that smelled like heaven – and it was fantastic.


Once in Boscobel we settled into our hotel, preparing for a few days of rest and relaxation near the pristine waters. Tucked away and tranquil, Boscobel has a special place in my heart. For years I owned a home in the Seaclusion Condo Complex, a private oasis celebrating the natural beauty of Jamaica’s sea and flora. Looking out your window, you often felt like you were on a private boat in the middle of the sea, despite being on land – completely disconnected from the word and immersed in all that is raw and natural, without compromising luxury. Even the furniture is made of natural materials, a collective homage to Jamaican creativity with most pieces handcrafted by local artisans.


Often I filled my days there with simple pleasures, not least of all fishing from the shores right outside my windows, catching “long jaw” as Jamaicans call them, Needlefish anywhere else. Clean ‘em, salt ‘em and fry ‘em… delicious. We didn’t stay at Seaclusion this time, we stayed at the Beaches Resort nearby, however the natural beauty theme persevered, with lush gardens and a sprawling white sand beach and we were willing to forgo a little tranquillity for the resorts’ waterpark.


After a few days of in beautiful Boscobel and Ochos Rios, we embarked upon the three-hour drive to Negril. It didn’t feel half as long as it was, and it was easy to know when we had crossed the town borders into Negril – the hotels. Negril is one of Jamaica’s premiere destinations, a resort town if you have ever seen one, spotted with more spas, resorts, and restaurants than there are residences. We stayed at one of the many hotels located right on the famed Seven Mile Beach – an expansive stretch of soft white coral-sand from horizon to horizon.


Despite my ties to Jamaica, I have not spent very much time in Negril previously so I was happy to explore. We walked along the beach, or as far as our legs could carry us, hopping from the various beachfront restaurants and bars. Negril has made a booming business of catering to tourist tastes and it shows, the various bartenders and restaurateurs kept us happy and in the party mood as we bounced along.


None of the bars stands out quite so much as Rick’s Café, past the beach on the West End Cliffs. The café predates Negril’s rows of resorts, opened in 1974 when the town was a sleepy fishing village. Rick’s Café has been offering the type of laid-back, no worries party vibe most associate with Jamaica ever since. We stopped by in the late afternoon, hoping to catch what the locals agree is the best sunset view on the island. Situated right on a cliff facing the west, the sunset was breath-taking.


However, the real excitement came when my friend took a leap of faith, quite literally, cliff diving from the look out into the cerulean waters 40 ft. below. It has become a tradition at Rock’s Café and they have several platforms at different heights to suit jumpers of various courage levels. As someone who has spent much of his career analysing and managing risk, I decided to sit this one out.


Before our drive back to Kingston, we stopped one last time at what had become our favourite breakfast place, “The Sweet Spot” for what may be Jamaica’s best coffee and some incredible ackee and saltfish, ironically the national dish of Jamaica though neither of the main ingredients are native. The return drive was a sleepy ride – four hours of hills, lush vegetation, and charming residential parishes. We basked in the sun and enjoyed the breeze, as usual treating our taste buds at roadside stalls along the way.


Once back in Kingston, we found ourselves too tired from the action packed road trip to enjoy the Kingston nightlife and spent our last day in Jamaica lounging in our hotel and savouring our last hours in the country. On the flight back, we peered out of the window at the Kingston Harbour, already nostalgic for reggae vibes on the Jamaican roads. America may claim to be road trip Mecca, and that may be so. But Jamaica is giving us a run for our money, with long winding roads, beautiful coastal and mountain scenery and interesting destinations along the way. If you think of lying out on a beach for days at a time when you think of Jamaica, think again. There is an entire island to explore and I wholeheartedly recommend doing so.

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