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To See the Real Jamaica, Skip the Resort and Go to Kingston

Restaurants + Bars Insider Guides Culture
by Rob Chursinoff May 11, 2020

Jamaica is the largest island in the English-speaking Caribbean and has a population of nearly three million. Jamaica is also home to one of the highest peaks in the Caribbean, the 7,402-foot Blue Mountain Peak, and 120 rivers, more than 200 species of orchids, and one Usain Bolt — the fastest human on Earth.

If you’re the type of traveler who feels more secure holing up in an all-inclusive, then you’ll likely head to Jamaica’s picturesque, heavily touristed beach towns of Montego Bay, Negril, or Ocho Rios. But a trip to Kingston shows all that makes Jamaica a Caribbean hub for arts, culture, and cuisine. The city of around 1.3 million people is set against the lush backdrop of the Blue Mountains, and with its bevy of boutique lodgings, fun festivals, and dancehall clubs, Kingston beckons you to explore. One thing is for certain — you won’t be bored.

Here, you can find yourself in a friendly Jamaican patty battle one day, then sipping one of the world’s top-rated coffees at a lush estate the next. You can wake up in a luxurious boutique hotel then head for an afternoon hike in the stunning Blue Mountains. Regardless of your itinerary, you should indulge in the Jamaican staples of jerk chicken or ackee and saltfish (the national dish) in many fine restaurants throughout the city. And yes, you’ll likely experience what Jamaica is best known for: Rastas; reggae, which you’ll hear everywhere; and rum, the country’s national drink.

Some of the lore surrounding Jamaica is true. Cannabis is commonplace, and since 2015, possession of up to two ounces is no longer a criminal offense and locals and tourists can legally consume at designated dispensaries. The average annual average temperature hovers around a near-perfect 80 degrees Fahrenheit. The Jamaican government recognizes Reggae music as the country’s most valuable export.

These are all reasons to head to the island, and Kingston in particular. But there’s so much more to know.

For a deep dive into Jamaican culture, look no further than Kingston

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One of the first things you’ll notice as you touch down in Jamaica is that smiles abound, from street hawkers and taxi drivers to restaurant staff and office workers. When a popular song comes on at a restaurant or high-end bar, it’s not uncommon to see the staff take a few moments to laugh and dance with each other. Jamaicans know the importance of having fun.

Start your day by fueling up with a hearty Jamaican breakfast, which is what islanders consider to be the most important meal. A Kingston favorite is Triple T’z Eatery, a simple restaurant with funky décor that serves up breakfast staples such as mackerel rundown (a stew), callaloo (steamed leaf vegetables), ackee (a fruit with the consistency of scrambled eggs when cooked) and saltfish, corned pork, dumplings, and Johnny cakes (cornbread).

Another favorite is the award-winning Boone Hall Oasis in the Stony Hill neighborhood. Here you can enjoy a popular Sunday brunch of curried goat, sweet plantain, fresh salad, and soup next to the Wag Water river.

For something fast and delicious, try the ubiquitous Jamaican patty. It’s what sushi is to Japan and tacos are to Mexico. The delectable pastries are filled with beef, chicken, seafood, or vegetarian options, with the flaky shell tinted yellow with turmeric. A visit to Jamaica without trying a patty is a sin. On top of that, every citizen pledges their allegiance to a local fast-food brand for a patty — you’re either a Juici or Tastee boy or girl, or (much less so) a fan of Mothers. Occasional Instagram hashtag battles break out between supporters of these three main brands. Pick your side.

Follow in Bob Marley’s footsteps

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With your belly full of patty, you’ll want to head Uptown to pay homage and learn about Bob Marley, the global face of Jamaica’s greatest export. Even if you’re not a fan of the legendary musician, head to Kingston’s most visited site, the Bob Marley Museum. The museum offers a fascinating look at the life of one of the most influential musicians in the history of popular music — a man who brought Rastafarianism, reggae, and Jamaican culture to the masses. For $25, you’ll get you a 75-minute guided tour of the two-story colonial-era house where the reggae star lived and recorded from 1975 until his death in 1981.

At each stop along the tour, your knowledgeable guide will prompt a group singalong to the relevant Marley song for that specific point of interest.

A vast array of gold and platinum records and Grammy awards adorn the walls in various rooms, with photographs, paintings, posters, and media clippings in others. Alongside these treasured mementos are Marley’s guitars; costumes worn by his backup singers, the I-Threes; and Marley’s famous working man’s denim shirt which he donned at concerts around the world.

At the rear of the house is the spot where gunmen snuck in one day in 1976 in an attempt to assassinate Marley, evidenced by bullet holes preserved in the walls.

In another, more pleasant area of the house is the wood-paneled recording studio of the former Tuff Gong Records, replete with original mixing boards where hits like, “No Woman, No Cry,” “Buffalo Soldier,” and “Could You Be Loved” were recorded.

Experience Jamaica’s national drink

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There’s always time for rum on Jamaica, especially with Bob Marley’s melodies floating around in your head and some legal medical marijuana from Kaya Herb House, Itopia, Epican, or another dispensary.

Feeling irie? Good. Quench your dry mouth and wet your palate with a dram or three of rum — Jamaica’s national drink. If you’re a fan of classic cocktails like the mojito, dark ‘n’ stormy, daiquiri, piña colada, mai tai, Cuba libré, and yes, even Long Island iced tea — or you simply want to stave off scurvy after a long bout at sea — then rum is your key ingredient.

While Barbados is widely considered the birthplace of rum, Jamaica has the honor of honing the rum-making process and putting the amber-hued spirit on the global map.

One of the best places to experience the craft of rum-making is at the 265-year-old Appleton Estate, a scenic two-and-a-half-hour drive west from Kingston into the heart of the island and its lush Nassau Valley. Once there, take in the view overlooking miles and miles of sugarcane fields that merge with the green hills far beyond. know that underneath your feet are the fertile soils and mineral-rich limestone waters that contribute the unique terroir of the distillery’s product.

Presiding over all this time-honored craftsmanship at the estate is the affable and passionate Joy Spence, the first woman in the world to be appointed Master Blender in the late 1990s. During tours of the estate, you’ll be able to taste wild fermented molasses, a key ingredient that gives Jamaican rum its distinct, full-bodied funk.

Other qualities define the island’s amber gold, as well: It’s made using all-natural GMO-free yeast, it’s aged in 40-gallon American oak barrels, and never in any step of the process are artificial flavors or sugar added to rum. Just fermented pure sugar cane, whose juice you’ll be able to try after volunteering yourself for a few laps turning the cane press.

Once you’ve taken a short and secretive (no photos or video allowed) walk through the sweltering steampunk world of the distillery, you’ll be thirsty. Lucky for you the tour concludes with a tasting led by professionally trained rum experts.

Eat, and then eat again

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En route back to Kingston from Appleton Estate, there are two must-stops for food. The first is halfway up the long Spur Tree Hill road in Manchester. There, underneath a Banyan tree, you’ll spot a man named Wayne stirring a big boiling pot of his famous peanut soup on the side of the road. If, like myself, you’re allergic to peanuts, then treat whoever you’re traveling with. Word from my companions, even days after they tried the thick, aromatic soup was that it was the best thing they ate the entire trip.

Stop number two is at Fancy Fruits Health’staurant in the mountain town of Mandeville. One part fresh fruit and health food market, one part restaurant, Fancy Fruits is 100 percent ital (natural) Rasta food. Friendly, soft-spoken co-owner Yahya El will gladly take the time to tell you that in order to assimilate mind, body, and spirit, one needs to enjoy raw, fresh food prepared without fire, sugar, salt, or artificial preservatives.

For other traditional, hearty cuisine there’s a bevy of fine food choices once you’re back in the capital. Redbones Rooftop in the stylish boutique R Hotel is a cultural hub in Kingston. The open-air rooftop bar and restaurant has hosted live music, book launches, art exhibits, poetry slams, and theater in its numerous locations since 1996. The current location in the New Kingston neighborhood offers you panoramic views of the city all while savoring the recommended jerk chicken pasta and, of course, another round of dark ‘n’ stormies. If you’re there during the day, pop down to the gallery in the basement for the latest exhibits by celebrated artists.

For something more local, head downtown to Gloria’s Seafood City at the waterfront’s newly renovated Victoria Pier. The airy, nautical-themed restaurant is bright, loud, lively, and friendly. It’s the kind of fun Jamaican vibe where, in the middle of tucking into a giant seafood platter, curried lobster, or sweet onion blue crab, you might be asked to jump up and join a drink chugging contest.

Get out on the town

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Let the rum party continue. The ultimate celebration of Jamaican rum is the lively Jamaica Rum Festival held in the leafy, palm-treed surroundings of Hope Gardens. You can take in seminars led by Joy Spence and other notable professionals in the rum industry, participate in cocktail making workshops, or learn to tweak your palate at a rum tasting. Then, once sufficiently tipsy, saddle up to some locals at the main stage and shake your booty to the likes of Kymani Marley, Capelton, Naomi Cowan, Spragga Benz, Freddie McGregor, and many more.

A trip to Kingston would not be complete without enjoying its famous nightlife. A good starting point is the Regency Bar & Lounge in the opulent, Old World-styled Terra Nova Hotel. The Regency is a chic, laid-back lounge with an outdoor patio where many in the capital gather before heading off for more raucous venues.

Fiction Nightclub calls itself Kingston’s premier nightclub, and for good reason. It’s one of the city’s hotspots for dancehall music, upscale parties, and a place to rub shoulders with international celebrities. Pro tip: Don’t go too early as parties start late in the city.

The Sunday evening highlight for many in the capital is the legendary Kingston Dub Club. Situated in the tony hills overlooking the city — right across from Rita Marley’s estate — the club is home to the Rockers Soundsystem and is dedicated to Rastafarian culture and music. Dub Club is operated out of the home of Karlyle “Gabre Selassie” Lee and has an outdoor dance floor, a store, and a bar and patio serving ital food with a stunning view of Kingston. You’ll find plenty of locals here mingling with international tourists, everyone enjoying the soulful music, and the spicy scent of the “herb” drifting through the air. Like Dub Club’s saying goes, “the only good system is a sound system.”

Don’t forget about the coffee

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After a night out where you probably had a little too much fun, you’ll definitely need some world-renowned Blue Mountain coffee. A 40-minute drive into the lush hills 2,600 feet above Kingston is the 200-year-old Craighton Coffee Estate.

A casual hike through the plantation will bring you to a gazebo surrounded by coffee bushes and a magical view of the mountains and villages around.

What makes Blue Mountain coffee so sought after by discerning coffee drinkers around the world is the blend of perfect climate, soil fertility, hours and angles of sunlight, and plentiful mists and rainfall found in the region. Add a cheerful, knowledgeable, and music-loving master roaster and guide in Alton “Junior” Bedward, and you get an exotic, exciting, and sensuous brew with a unique and definitive flavor. A tasting on the patio of the estate house is included.

For those that enjoy nature and a good, hearty hike, the mountains that rise up to make Kingston’s back yard are not to be missed. The peak of Blue Mountain sits at 7,402 feet, the highest point in the Caribbean. So, while you may start your day wearing shorts, make sure you pack rain gear and warmer clothes for the mountains as temperatures can quickly drop.

The Blue Mountain peak hike is labeled as hard, but if you’re a brisk hiker, and the weather cooperates, the hike can be done in under six hours. To get there, pre-book a taxi (make sure it’s not a car with low clearance) or rent a 4×4 and then prepare for a one and a half-hour drive from Kingston along narrow, snaking roads into the spectacularly lush mountains. After the pavement ends the drive continues along steep, rutted dirt road through charming cliffside villages until you reach Whitfield Hall, where most of the hikes begin.

You can reach the peak without a guide, but I would not recommend it as it’s easy to take a wrong trail. Besides, you may end up being led by a charming and knowledgeable 70-year-old Rastaman with tall tales and plenty of energy to keep pace with you. Near the top you’ll pass through a lot of changing vegetation — the Elfin Wood being the most magical. Once at the peak, if you’re fortunate to have a cloudless day, you’ll be able to see the north and south side of the island stretching far below you to the sea.

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