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48 Hours in Kingston, Port Royal & St. Andrew

In the opening scene of Disney’s third Pirates of the Caribbean, the treasured Jack Sparrow is beaching the shores of Jamaica. Eyeing Port Royal through his monocular, Jack drops from his lookout post to the deck of his tiny boat. As he saunters onto the town docks his boat capsizes behind him.

Port Royal, Jamaica was: once the largest city in the Caribbean. Was: At the height of its fame in the 17th century, known as the “wickedest city on earth.” Where once-lived Jack Sparrows drank themselves to poverty at port pubs, throwing away pirate gold at women and wine. Where rumour has it, pirates would buy pipes of wine, place them on the street, and, oblige everyone that passed to take a swig. Effectively, rendering the entire town drunk by sunset.

Naturally, a city that lived as fantastically as Port Royal could only end on the same note. In 1692 the entire city, hit by a severe earthquake, capsized and sank below sea level. Its stories and adventures almost quite literally disappearing into thin air, or rather, sinking to the bottom of the seabed. Punishment for their sins, claim God-fearing Jamaicans. In place of Port Royal rose Kingston, an until-then agricultural village the town over.

Maybe Jack and his sinking ship actually knew more than they let on, eh?

Since its founding in 1692, Kingston has developed Jamaica’s other R and R: reggae music and Rastafarianism! Rising from the history of its illicit past is an urban city marking its own unique cultural and artistic scene. Bob Marley. Usain Bolt. Rasta-Ital cuisine. The yearly Jamaican Bacchanal. Kingston has continued to develop as uniquely as its 17th-century predecessor. Captain Davey Jones would be proud.

Here are our top places and faces for a weekend in the city just a short trip from Carleva Bay!


Tracks & Records

The aptly named restaurant is owned by no other than Jamaica’s own Usain Bolt. It features more than a whopping 45 televisions (including one 20-foot TV!), truly a sport bar dream. The menu showcases both classic Jamaican dishes, and fun fusion dishes like jerk chicken quesadillas and jam Asian Cobb salad.


Track and Records is in New Kingston, the “Uptown” business and playground for well-heeled Jamaicans. Heading the other way, economically as well as geographically, toward “Downtown,” check out a special shop in Regal Plaza, in the Crossroads section.


Veggie Meals on Wheels

Good news for vegetarians visiting the island: Plant-based food is generally much simpler to come by than in other neighbouring countries, thanks to Jamaica’s Rastafarianism movement. Based on a broader idea that “everyone has a right to eat healthy”, the Veggie Meals on Wheels offers ital-friendly dishes including brown stew tofu and ackee with sweet potato. You’re in for culture too, with music, book readings, great conversations. New things popping up every week. Business has been so popular they now cater even in the greater Brooklyn, New York area.



Life Yard

Near the sea in Downtown Kingston, the coolest new cultural spot to visit is Life Yard, an organization created by enterprising young Rastafarians. Committed to bettering themselves and their community, they started out by beautifying their area with fascinating murals that are worth seeing. Life Yard does wonderful, empowering work with the local children, and provides employment opportunities for locals. While there, you can have lunch in the Ital restaurant inside their compound, see their urban farm and tour the neighbourhood. Their latest ventures are a store and providing tours to other interesting cultural sites in Kingston. They totally deserve your support, plus, you’ll enjoy the off-the-beaten track visit!



Mount Debre Zeit Records and Variety Store

A trip to the capital of reggae music would be incomplete without a stop at a records store! Located in Papine, at the start of the road up to the Blue Mountains (make sure to stop by on your trip to the Holywell National Park below!) Zeit Records is easily the best place in town to pick up Jamaica’s latest musical drops. Owner Ras Haile Malekot is a DJ himself, and knows many of the artists his shop sells.



Bob Marley Museum

Not a stop to be missed for those interested in the history of reggae music. The museum is situated in Bob Marley’s former home, and offer well-practiced tours throughout the week. For another perspective on reggae’s golden years, take a look at the more recent Peter Tosh museum.



National Gallery of Jamaica

The National Gallery does a remarkable job at balancing Jamaica’s historical and contemporary art. Being the oldest and largest art gallery in the Anglophone Caribbean, it also sets a strong precedent for the surrounding Caribbean nations. One of the permanent ‘Art in Jamaica’ exhibitions tells the story of the nation’s history from the original Taino people, to Spanish and then English colonization.

National Gallery of Jamaica, Special Exhibit

Girl Surprised, by David Miller Jr. National Gallery


Devon House 

This is another favourite that’s just a skip and a jump from the Marley Museum. The “House” is the former home of Jamaica’s first black millionaire, the 1820-born George Stiebel. Exhibits narrate his epic journey towards becoming a gold trader in Venezuela, eventually returning back home to Jamaica to pursue local philanthropy. The grounds are beautiful and well-preserved. Several cafes, restaurants and interesting shops dot the site, including the famed Devon House Ice Cream parlour. A Carleva House favourite! We recommend the rum and raisin flavour. And if you love lounging in the hammock in our front yard, get your replica here!


Temple University group at Devon House



Holywell Recreation Area and Blue Mountain National Park

Considered the champagne of coffee, Blue Mountain brew is an international best seller and a nation-favourite local bean. Head over to Eleni’s Bakery to grab your own cuppa joe, then start planning your trip to the mountains to see the mighty bean in action. Going way up to almost 7,500 ft above sea level at Blue Mountain Peak, the range (officially, the John Crow and Blue Mountain National Park) includes recreation areas with marked trails and information centers.


About an hour drive from the city into the Blue Mountains, you’ll feel like you’re in a totally different world. Looking down on Kingston and Port Royal from about 1 km up high, the views are fantastic! The 330 acre Holywell Park includes rest areas, gazebos, play areas for kids, nature walks, and simple cabins for the eco-hardy (reservations needed). From here, you can go up Blue Mountain Peak, tour a coffee farm, watch birds, hike to waterfalls, and more.

Blue Mountains Holywell Park nature walk, source:

Blue Mountains Holywell Park cottage, source:

Blue Mountains Holywell Park bird-watching tour, source:

Up high on the Blue Mountain Peak trail

Leaving the coffee farms for the higher reaches of Blue Mountain Peak

A beautiful day with students on the Blue Mountain Peak trail

Now that’s balance!

Coffee farmers selecting beans for export under the Blue Mountain label. One of the unique aspects of the coffee is that it is packaged in barrels made of Aspen wood.

Coffee as it comes into the processing facility. Yes, the berries are red!


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