Known as the unofficial capital of the Caribbean, Jamaica has gifted plenty to the rest of the world. From revolutionaries like Marcus Garvey and music rooted in the sounds of Bob Marley, to delicious eats like jerk chicken and ackee and saltfish, Jamaican culture has influenced a generation. So it’s no surprise that native Jamaicans like Diana O’Gilvie return to their homeland after year away, and proudly share insight into how visitors can fall in love with the old and new vibes on the island.

Traveling to Jamaica soon? O’Gilvie shares her take on what you should see, eat, and do in Jamrock.

I was born and raised in Kingston, and after traveling and living on three continents, it was time to return home. As a returning resident, Kingston is delightfully nostalgic and new at the same time.  As a destination, Jamaica’s capital city is woefully misunderstood due to its gritty reputation, but the city is more relaxed than headlines would have you believe.  There is a pulsating nightlife, a party for every day of the week, a booming local music scene and quiet, secluded enclaves perched on hills with spectacular vistas.  Kingston is a crash course in Jamaican culture, and all one needs to do to experience it is venture a little further below Half-Way Tree to downtown, and rub shoulders with electric energy.


When I first discovered Fleet Street in downtown Kingston I was impressed with the art-covered stretch of road. At first glimpse, Fleet Street is like any other block in Kingston. Families are out playing football and volleyball; kids are riding their bicycles and joy riding on pushcarts. However, in the middle of the block, artists of the Paint Jamaica project have turned abandoned buildings and street corners into electrifying and vibrant murals. The artwork is some of the most stunning and thought-provoking you’ll see on the island.  A few doors down from the murals sits Life Yard, a delightfully hidden garden oasis operated by Rastafarian community members. Every available space on the property is used for growing crops such as plantains, breadfruit, apples, bananas, yam, peas, as well as compost heaps. Life Yard hosts international educational groups where learning exchanges take place to share new agricultural techniques. After a stroll through the artwork and the farm, cool off with freshly squeezed, or blended, juice for a nominal fee.


Jamaica is home to arguably the best coffee in the world, Blue Mountain.  A short thirty minutes drive up the winding mountains leaves Kingston behind in a spectacular vista. I especially like heading up to the mountains on a weekend and visiting Café Blue in Gordon Town.  The cooler temperatures in the hills make for an even warmer cup of coffee. I always order a mocha latte, make my way to the back verandah and sit on one of the wrought iron chairs to sip my coffee and drink in the view. If I am lucky, a humming bird or butterfly will stop by to say hello. When hunger pangs cannot be ignored, Crystal Edge, next door, serves up some delicious local cuisine. Proprietor and cook, Miss Winsome only makes about three or four dishes everyday. Her coffee crusted baked chicken with rice and peas is simply delicious.


It might be hard to believe, but up until a few years ago it was hard to find good live roots music in Jamaica. Thanks to a groundswell in support of artists like Chronixx, Jesse Royal and Protoje, there is no shortage of roots and dub music in Kingston. Leading the roots pack is Dubclub at Skyline in Jack’s Hill on Sunday nights. These days the new JA$500 (around $4 USD) cover charge may keep some locals away while the Lonely Planet lookalikes party inside. Still, the music is always good at Dubclub as the sound system speakers pump out classic reggae tunes with scintillating grooves. Drinks are still cheap and light eats are available. I adore the saltfish fritters (JA$100 each, less than $1 USD) and Sorrel Red Stripe.

Kingston is also really famous for its sound systems–giant speakers stacked around a street or an inside venue with a ‘selector’ or DJ playing the latest songs. This is dancehall culture in its purest form. In the 1960s, sound systems roamed the streets where artists honed their lyrical skills. Musical street battles meant the victor had enormous street cred and an even bigger following at the next dance. Sound system parties are part of Kingston’s DNA. Think part block party, part fashion show, with a generous mix of acrobatic dance moves and you’ll get the picture. Oftentimes, communities close down an entire street to accommodate a late night dance. Even better, they are perfectly safe as residents are responsible for security and they don’t take too kindly to violence at their events. If you attend one, just leave obvious valuables behind and have a good time. Head to Stone Love HQ for the Weddy Weddy Wednesday party, held weekly. But prepare yourself for some bent over, wild, dutty wine and head top dancing.


Before returning to Jamaica, my hotel of choice was Spanish Court Hotel in New Kingston. Built in 2009, Spanish Court is Kingston’s newest hotel in thirty years. The rooms are extremely comfortable with modern designs and top-notch amenities. My favorite part of the hotel is the rooftop. The Sky Terrace Bar area features a delightful 50-feet long infinity edge lap pool, and the sun deck and full service bar make it the perfect tropical hideaway in the concrete jungle.

-As told to Danielle Pointdujour


Danielle T. Pointdujour is a Brooklynite living the passport life to the fullest. With over 70 countries under her belt, you can always find Danielle traveling the globe in search of new experiences and the hottest luxury hotels. You can follow her writing, musings and global adventures on her blog Hotel Whisperer and on Twitter and Instagram.