The Caribbean Islands have all the trademarks of a luxury holiday destination. White, sandy beaches looking out onto the azure blue seas, and a pina colada waiting for you at a spot beneath a swaying palm tree.

But the group of tropical islands is more than just this picture of halcyon days, and each corner of the archipelago has its own distinct culture. Whether you’re journeying into the pulsing urban hub that is Jamaica or would rather laze under the sun with a book in Turks and Caicos, you’ll find your own slice of heaven there.

Sure, it might take awhile to get to the Caribbean from Singapore (the average flight time is a little over a day). Why should you also fly halfway across the world just to be in a climate so similar to ours? For starters, you’re not simply going on a holiday – you’re escaping on a vacation. The unspoiled nature of the Caribbean islands serve more than a purpose of rejuvenating your soul. It’s far enough that you can really take a break while being acclimatised so you can afford to pack lightly. The islands are also so far away that work becomes an afterthought, and you have the perfect excuse for neglecting that non-essential email.

If you can’t make up your mind as to which island to visit, or if you should just see all, here’s the lowdown on 6 idyllic Caribbean islands to help you plan your travels much better.


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Montego Bay in Jamaica. (Photo: Holger Leue/Getty Images)

Lovers of reggae and Bob Marley need this island on their itinerary. The cultural heart of the Caribbean with good vibes aplenty offers more than a groovy beat: there’s beautiful sights both on the beach at Montego Bay and by the lush Blue Mountains. With a recent a push into Jamaica’s health and wellness tourism, we can soon expect it to become the next big holistic destinations.

Tip: If you want to experience the true Jamaica, stay in a locally-owned guesthouse or villa instead of the glitzy hotels you’re 5 seconds away from Googling.


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The picturesque streets of Havana in Cuba. (Photo: Spencer Everett/Unsplash)

As the largest island within the Caribbean, Cuba is a cornucopia of cultural delights that will open your eyes to a whole new world. Despite its rocky relationship with the United States, a sight to behold on the streets of the country would be the many vintage convertibles from Detroit – Karl Lagerfeld in 2017 used the streets of Havana to present Chanel’s resort collection for that season with a parade of cars flanking the runway.

Tip: We’d recommend travelling to Cuba anytime from December to April, as the hot summer months can get stifling and weather-averse.

Turks and Caicos

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The Provinciales Beach in Turks and Caicos. (Photo: Libby Giambrone/Unsplash)

Those who just want to relax on a lounge chair with the sea breeze should head to Turks and Caicos. This “hidden gem” of the Caribbean is a group of 40 islands flanked on all sides by turquoise waters home to some beautiful coral reefs. Its barrier reef stretching close to 547km makes it a perfect destination for the diver.

Tip: You’d want to be staying in the island of Providenciales which is where the iconic Grace Bay Beach is (voted multiple times as TripAdvisor’s number one beach in the world).

Saint Lucia

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The pitons o Saint Lucia. (Photo: Daniel Hjalmarsson/Unsplash)

Saint Lucia is not your ordinary Caribbean island. Two landmark “pitons” or volcanic plugs greet you as you’re flying in, hinting at the lush splendour of the island. Nature lovers would have a field day in Saint Lucia exploring the roaring waterfalls hidden within the rainforest, while foodies can indulge in the local cuisine that draws from Caribbean, African, English, and French influences.

Tip: Take a trip on a catamaran out into the sea to view the island from afar. Thank us later (and tag us in your Instagram pictures).


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Yes, there are wild flamingos in Aruba. (Photo: VanWyckExpress/Getty Images)

If you’re all for the sea, sun, and beaches, Aruba is the destination you need to visit. Its arid climate with clear skies and easily-accessible beaches are just some of the reasons why many escape to its shores during winter. Plus, Aruba is just shy of the Caribbean’s “hurricane zone,” making it one of the region’s safest islands.

Tip: Access to the famous Flamingo Beach is only available through the Renaissance Aruba Resort in Oranjestad. You can either book a stay there, or purchase a day-pass at USD$125 per person.

Saint Barthélemy

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The Gustavia Harbour in St. Barths. (Photo: Andrew Rowat/Getty Images)

Saint Barthélemy, known better as St. Barth’s, is where the jetset escape to with their private jets and Birkin bags. It’s a unique confluence of both exclusivity and accessibility, where you’re likely to be sunbathing on Nikki Beach next to a socialite. There are many accommodation options like the Christian Liagre-designed Le Sereno, the Cheval Blanc, or the Eden Rock. Be sure to visit Le Select (the bar that inspired Jimmy Buffet’s “Cheeseburger in Paradise) and Le Ti St. Barth for an after-hours cabaret show.

Tip: For the ultimate seclusion, book a private villa from Luxury Retreats or St. Barts Blue.

Josiah Neo
Josiah Neo is a tech writer who contributes occasionally to the fashion, travel, and culture beats. When he’s not busy keeping up with the keynotes, he’s probably stuffing his face with the best Melbournian donuts (at Shortstop, BTW) or watching his favourite esports team, the Los Angeles Valiant, pummel their opponents into oblivion.