Gay Jamaica in one week: Montego Bay, pristine beaches, Gay Kingston, and much more

Where idyllic pearl-white beaches give way to craggy clifftops and rushing waterfalls, and laidback island vibes conjure dreamy days of reggae and rum, Jamaica is a patch of paradise that almost needs no introduction. There’s an undeniable barefoot ease to this jewel of the Caribbean—though thrill-seekers won’t want for adventures, whether it’s hiking through forested mountains, snorkelling over colourful coral, or cliff jumping into crystalline waters. Yet, the alluring beauty of Jamaica is not only in its natural wonders but also in its massive influence on the world. From Bob Marley to Usain Bolt, this is a country of superstars, one that has inspired the work of countless artists and creators. Dive deep into this legendary nation with our ultimate gay Jamaica itinerary. From buzzing Kingston to bohemian Negril, here’s how to spend one week in the green garden that is Jamrock.

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Tailor-Made Aruba & Curacao

If you’re looking for something above and beyond pure paradise, look no further. Renowned for the quintessential Caribbean experience – think white sands and swaying palm trees – Aruba and Curacao is one of our favourite twin-centre Caribbean vacations.

Kingston | Photo: Ricardo Reid

LGBT situation in Jamaica

There’s no sugar-coating Jamaica’s history of homophobia and continued LGBTQ discrimination. Members of the gay community remain victims of oppression under a Colonial-era Penal Code criminalizing same-sex relations, called ‘buggery laws.’ While a rise in Jamaican activists and increasing visibility is challenging these persecutory laws, censorship against LGBTIQ rights and disparaging inequality and harassment towards the gay in Jamaica remain.

That said, gay travellers to Jamaica are less likely to face discrimination so long as they stay around well-trodden tourist areas. The 2017 tourism minister even declared Jamaica a country for all tourists, regardless of sexual orientation. To be safe, exercise discretion in public and avoid displays of affection. When it comes to booking accommodation in Jamaica, most all-inclusive resorts and mid to high-range hotels welcome same-sex couples.

Photo: Joey Nicotra

Photo: Rock Staar

When to Visit Jamaica

If you’re chasing endless sunshine, mid-December through mid-April is the time to visit Jamaica. Yes, this is peak season, so expect higher prices and tides of tourists at popular beach spots—the tradeoff for the driest time of the year. Throngs of frat boys descend on the island during spring break (mid-March through April), so we recommend avoiding this time if you’re not keen on reverberating college parties. The rest of the year in Jamaica is more wet and humid; June 1st – November 30th is the official hurricane season, and October and November tend to be Jamaica’s rainiest months. For the best value and a solid shot at the weather playing ball, late November and early December offer reliable deals ahead of peak crowds.

Travel Tips

While jerk chicken is arguably the most famed of Jamaican dishes, there’s more to the island’s cuisine than its drool-worthy spice rubs alone. Influenced by both the Old and New worlds, many Jamaican dishes revolve around yams, rice, and plantains. Don’t miss saltfish and ackee, a hearty breakfast that doubles as Jamaica’s national dish. There are also heaps of fresh local fish and juicy tropical fruits to be had, best washed down with a swig of spicy, sweet rum. When it comes to hydrating, the tap water is safe, but it’s best still to stick with readily available filtered water.

Marijuana is synonymous with a Jamaica beach getaway for many. However, it’s only recently that the government decriminalized the possession of ganja, and there remain ongoing questions about the ramifications of tourists purchasing marijuana (specifically its effects on local crime.) Should you decide to imbibe, you’ll have no trouble finding ganja from beach hawkers or even roadside stands.

Travellers seeking out wildlife will find countless opportunities to explore the marine world in its natural habitat. Avoid captive animal centres, many of which have questionable practices.

Photo: Rock Staar

Days 1 & 2: Kingston

Sandwiched between the Blue Mountains and the world’s seventh-largest natural harbour, Kingston is a fitting start to any gay Jamaica travel itinerary. A UNESCO Creative City of Music, Kingston is a cacophony of sights, sounds, and smells—at times overwhelming yet never uninteresting. The city consists of two halves. Uptown is a bevvy of towering skyscrapers, where you’ll find some of the city’s top hotels and restaurants. Downtown is bursting with historic buildings, bustling markets, and world-class museums. While the two aren’t always a seamless blend, together, they provide a beguiling portrait of modern Jamaica.

Some of the top things to do in Kingston include the Devon House, the former residence of Jamaica’s first black millionaire, and the Bob Marley Museum. From here, hop into any of Kingston’s contemporary art galleries for a guided tour of Jamaica’s kaleidoscopic art culture, or head straight to the open-air Kingston Craft Market to pick up a colourful souvenir. Whatever you do, don’t miss Port Royal; once the ‘wickedest city on Earth,’ the ancient Pirate capital of the Caribbean is now almost entirely underwater. From here, uninhabited Lime Cay is just two miles south, a worthwhile add-on.

Kingston is a cultural mecca, but that doesn’t mean it wants for natural marvels, too. On a clear day, Holywell Park is the spot for sweeping city views from Port Royal to Portmore. The 300-acre park lies at 3,200 feet above sea level, a wonderful escape from the perennial hustle and bustle below. Climb even higher with a trek to Blue Mountain Peak, Jamaica’s tallest point visible from virtually anywhere in Kingston. Back in the city, New Kingston is the spot for heady nightlife with some of the best reggae artists on the planet.

Kingston | Photo: Rock Staar

Blue Mountain | Photo: Yves Alarie

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With its swaying palms and sugar-fine sands, Ocho Rios is the postcard for swoon-worthy Caribbean vacations

Days 3 & 4: Ocho Rios

With its swaying palms and sugar-fine sands, Ocho Rios is the postcard for swoon-worthy Caribbean vacations. It hardly comes as a surprise then that this once sleepy fishing village is now a popular tourist hub. Many a cruise ship frequent Ocho Rios’ shores, and, admittedly, it can get quite crowded. That said, avoid the frequent dockings, and you’ve got all the trappings for a balmy tropical escape in paradise.

The calm, turquoise water lapping on the sands of Ocho Rio is tonic for the soul; we’d forgive you for spending your entire two days here on one of the many sun-soaked bays. Turtles Beach, James Bond Beach, and Paradise Cove are some of the best. Outside your resort walls, there is a veritable playground of wild wonders. Dunn’s River Falls cascades 600 feet into a cool swimming hole, warranting its spot as Jamaica’s most visited attraction. Jungle zip lining, river rafting, and rainforest bobsledding are some of the more exciting offers to be had at Mystic Mountain. Nature lovers seeking something a little less exhilarating yet just as rewarding can hike along Little River, where exotic birds and flowers abound.

Ocho Rios | Photo: Lakeisha Bennett

Days 5 & 6: Negril

Beloved hippy haven of the early 1970s, Negril hasn’t lost its bohemian charm—even after some 40 years of development. Here, precipitous limestone cliffs give way to crystal-clear water. The jagged coastline is dotted with swanky boutique hotels, most with staggering ocean views from their treetop locales. Join the friendly locals as they daringly dive into the azure waters below or simply soak up the unquestionably cool vibes with a refreshing Red Stripe in hand.

The north part of Negril is graced with some of Jamaica’s best and longest beaches, including ever-popular Seven Mile Beach. There’s plenty of tasty local restaurants and buzzing beach bars when hunger strikes. For something a bit more secluded, Calico Jack Pirate Island is a rustic bar hidden away on a private island. A relative newcomer to Negril’s hip and happening scene, expect authentic Jamaican cuisine, unspoiled snorkelling, and zesty cocktails—all in a setting that pays homage to Jamaica’s fascinating pirate past.

Photo: Rock Staar

Photo: Caique Silva

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The jagged coastline is dotted with swanky boutique hotels, most with staggering ocean views from their treetop locales

Day 7: Montego Bay

Rounding out our gay Jamaica itinerary is Montego Bay, an enchanting Jamaica beach that is also home to one of the island’s most thrumming city centres—right behind Kingston for its unscripted depiction of modern Jamaica. Lovingly dubbed MoBay, the shiny Jamaica all-inclusive adults-only resorts lie far outside the gritty urban centre, with The Hip Strip (Gloucester Avenue) and its mid-range hotels falling somewhat in between the two.

Most of the best beaches in Montego Bay are private, which means you’ll pay for access. Doctor’s Cave Beach is one of the most sought-out for good reason. And if you’ve yet to leisurely float down a river on a bamboo raft, a quintessential thing to do in Jamaica, then Montego Bay is the spot to hop on and soak up the island’s serene inland countryside.

MoBay is a foodie’s delight, so finish up your Jamaica travel itinerary by eating your heart out. The Pelican Grill is a city landmark serving up bowls of steamy stewed oxtail and addicting deep-fried cassava flatbreads. For decadent cuisine coupled with big-time thrills, Pier 1 is a waterfront seafood restaurant that doubles as one of the city’s top dancing venues. Finally, if you’re in Jamaica with your special someone, Sugar Mill Restaurant is as romantic as it gets.

Montego Bay | Photo: GianlucaFerrobr

Photo: Sean Witter

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Photo: Yves Alarie

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