If turquoise water, white sand beaches and fiery pink sunsets are what you’re after, then there’s no better place on earth to visit than the Caribbean Sea. Unsurprisingly, the Caribbean is reliably popular every winter, as weary travellers head south in the colder months, seeking sunny days and rum-fuelled nights from the Bahamas down to Trinidad and Tobago. The Beach Boys popularized the Caribbean’s tropical allure in their melodies, and Bob Marley immortalized its soul and ethos in his lyrics. Mustique was a favoured getaway of Princess Margaret looking to escape the press—these days, Beyoncé evades the paparazzi by heading to St. Barts.
But there’s still much to the islands you’ve yet to discover. Even the most discerning, sophisticated traveller would be surprised to find they’d somehow missed these hidden gems tucked away alongside some of the most popular snowbird getaways on earth. So, if your idea of a perfect tropical vacation doesn’t include massive amounts of tourists, don’t be discouraged. There are more than 7,000 islands in the Caribbean archipelago, of which some are less discovered—and more luxurious—than the rest. From romantic, open-air resorts overlooking the sea in Saint Lucia to the pristine and picturesque beaches of South Caicos, here are the most elegant (and underrated) islands to visit in the Caribbean, guaranteed to bring visitors bliss and solitude (and five-star amenities, of course).
Turks and Caicos Islands, British West Indies
With its breathtaking white sand beaches and vivid aquamarine coast, the Turks and Caicos Islands have long been a favourite hideaway for the rich and famous. Keith Richards, Taylor Swift, Brad Pitt, Kim Kardashian, Oprah Winfrey and Rihanna are regular visitors to the Turks and Caicos Islands, world-renowned to have the best beaches in the Caribbean, if not the entire planet. The reason for this technicolour tropical paradise is that the sand consists of coral and shell (lending it’s blush-like colour), and the beaches reflect the island’s limestone foundation.
Most visitors opt to stay in Providenciales, the most famous island (and the one with an international airport). But there are eight main islands in the Turks and Caicos, and over 40 smaller islands and cays, which are pristine and uninhabited. We encourage you to hop on an inter-Caribbean flight from the airport to South Caicos, where the solitude (and romance) is unrivalled. The super-secluded 8.2-square-mile island is home to a population of less than 1,600 residents, so you’re more likely to spot a wild donkey roaming outside your villa than another human being. The tourism industry that altered the other islands in the Turks and Caicos has yet to impact South Caicos: The island has four different types of cacti, but only three hotels.
Of the three hotels, Sailrock Resort is the best choice—the resort overlooks the Atlantic Ocean on one side and the Caribbean on the other. The first 5-star luxury resort on South Caicos, Sailrock opened in 2017, and it feels like you have your very own private island. Book a stay at Sail Rock, the first luxury resort in South Caicos, to capitalize on your whimsical surroundings. Sailrock is navigable mainly by golf cart, useful when navigating the property’s 770 tropical acres. Watch the moon set over the Caribbean Sea while sipping cocktails poolside at the Great House, or relax in a hammock overlooking that outrageously vibrant aquamarine water, rocking back and forth to the gentle surf.
But it needn’t be all rest and relaxation. South Caicos’ remote location within the West Indies archipelago is perfect for island-hopping. We suggest exploring the uninhabited islands and cays by boat. Snorkel one of the most magnificent reefs on the planets—the snorkelling in Turks and Caicos is among the best in the world —and sunbathe upon the secluded coasts of the myriad surrounding islands. The striking rock formations may remind you of Malta or Greece—though, with its distinct Caribbean flair, South Caicos has no real rivals in the Mediterranean. One visit to the island will have you convinced of its uniqueness. You will get a taste of authentic island living, not just in the natural beauty of your surroundings, but in your community. The spot to be on the weekend is Triple J’s Grill, which feels like a backyard barbecue—and is.
Leeward Islands, Eastern Caribbean
Turks and Caicos is part of the British West Indies in the northern Caribbean (alongside Bermuda, the British Virgin Islands, and the Cayman Islands), but from here on out, we’re headed south, to the far less well-known Eastern Caribbean. Home to Emerald Pools, Boiling Lakes and Champagne Reefs, Dominica is known as the “Nature Island” of the tropics. The landscape of Dominica, as its moniker suggests, is appropriately majestic. However, most would-be visitors are more likely to mispronounce the country’s name (it’s Domin-EEK-ah) and confuse its location (no, it’s not part of the Dominican Republic) than to list its stunning natural attributes. However, one visit to the island will convince the most well-travelled visitors to believe that the nation’s diversity is evocative of the best vistas from around the globe.
Though this island is relatively small, its diverse ecosystems resemble some of the most iconic landscapes on earth—not to mention some iconic places to stay (which has gotten a recent boost via the opening of the new Kempinski.) Dominica opened its first beachfront 5-star resort, Cabrits Resort & Spa Kempinski, Dominica, this past October in Cabrits National Park. The cliffside Fort Young Hotel overlooking the ocean in Roseau resembles the Mediterranean coast in Italy, and Pagua Bay House in Pagua Bay is heaven for those looking for a Bali-type immersive moment in nature, on the beach. But nature is unavoidable on the island—just driving through the country, there are moments of breathlessness.
Dominica’s nickname is certainly well-earned. The relatively tiny island is home to nine of the 16 active volcanoes in the Caribbean. While this may sound overwhelming to the leisure traveller—and perhaps enticing to the adventurer—the nation’s beauty is something that can be appreciated by the entire planet. The hot springs and mud pots in the Valley of Desolation rivals Yellowstone—only without the crowds, of course. The Boiling Lake in Morne Trois Pitons National Park is the second-largest in the world (New Zealand’s Frying Pan Lake has top honour), and the jagged green mountains overlooking the water evokes Hawaii’s Na Pali Coast. The lush interior rainforests are reminiscent of the subtropical jungles in (relatively) nearby Belize.
While visiting, be sure to partake in some whale-watching (Dominica is also the whale-watching capital of the Caribbean, home to a year-round population of female Sperm Whales), and embark on a Boiling Lake Hike. Visit the Kalinago Heritage Center to learn more about the island’s history and the legacy of the people of Dominica. Afterward, go off-the-beaten-path (to delectable results) at Islet View Restaurant, located on an unnamed road in Castle Bruce, on your way home. Befriend your driver or a local for exact directions, and thank us later when you’re toasting on the deck with homemade plantain chips and rum punch.
Windward Islands, Eastern Caribbean
Our next choice takes us just south, from the “Nature Island” of Dominica to the “Spice Island” of Grenada, also located in the Eastern Caribbean. Grenada is a wondrous location for the discerning traveller since the selfie-wielding masses haven’t yet infiltrated every public space, and its breathtaking beauty is still mostly undiscovered to the majority of travellers, even those well-acquainted with the Caribbean. This can be partially attributed to its location, in the southern Caribbean Sea, merely 100 nautical miles off the coast of Venezuela. Less-motivated travellers will opt for closer islands when it comes to a weekend getaway, especially if they’re departing from the United States (the Bahamian island of Bimini is a mere 60 miles from Miami, for comparison.) Plus, if the north Caribbean Sea is already so gorgeous, why bother travelling several more airborne hours to the south?
Well, the beautiful island of Grenada is a pretty satisfying reason why adding a little extra travel time to your vacation is well worth it. The island of Grenada is gorgeously lush, mountainous terrain teeming with tropical wildflowers, while unexpected waterfalls and crystal clear lagoons abound in the tropical forests. The overwhelming natural beauty of this picturesque island was remarked upon as early as 1672, with the arrival of the French, who named villages Beaulieu (‘Beautiful Place’), Beausejour (‘Beautiful Residency’), Belle Isle (‘Beautiful Island) and Belmont (‘Beautiful Mount’). Book a room at Mount Cinnamon Grenada to best appreciate the vistas offered by the mountainous island nation and revel in the magnificence of the world-famous Grand Anse beach.
While the nation’s French influence is reminiscent of that other luxury island to the north, St. Barts, the atmosphere of Grenada is decidedly more relaxed. Despite being popular with its wealthy, well-known clientele who return year after year, Grenada has yet to catch on with popular culture at large. The island manages to remain just under-the-radar, even though Justin Bieber celebrated his 21st birthday in the country, which is quite the feat. The Canadian musician chose Calivigny Island as the setting for this momentous personal occasion, renting out the private 80-acre retreat. Though Calivigny is accessible via five-minute boat ride off the nation’s southern coast, the opulent oasis requires a far more significant investment in booking fees.
Similar to Dominica, people tend to mispronounce the country’s name on occasion (confusing the island with capital city in Spain). For both Grenada and Dominica, the stress is on the second-to-last syllable. Serious sailors needn’t be reminded of such basic facts, as Grenada has become a yachting capital of the Caribbean. The island’s popularity is a result of its safe harbours; the waters provide a haven protecting boats and mega-yachts from storms year-round. Additionally, the practice of traditional Caribbean sailing is kept alive and well on the island—we recommend booking a sunset sail aboard a Caribbean Schooner with Savvy Sailing during your visit.
Alongside sailing, rum is, of course, another tradition—as well it should be in the Caribbean’s Spice Island. The rum at River Antoine Distillery is so popular amongst locals, it is never exported (of course, the 150-proof liquid would never be allowed on a plane), so we suggest visiting the source for a taste of local flavour. Afterward, dance the night away at the Dodgy Dock, as you will undoubtedly have imbibed the liquid courage necessary to do so.
Windward Islands, Eastern Caribbean
Our next choice is the sister island of Dominica: the magnificent nation of Saint Lucia. Both Caribbean islands share a mountainous landscape (the Pitons are dramatic, overlooking the coast of Soufriere, and their pointed peaks are reminiscent of the (similarly named) Tetons in America’s Western states. However, the green hues of the lushly forested mountains resemble the Andes in nearby South America. But while Dominica, the Nature Island, promises a rustic escape, Saint Lucia is decadent luxury (and romance, but more on that later.) Both islands, however, offer the same promise of seclusion.
Just how secluded, you may ask? Well, your Saint Lucia Vacation isn’t complete without booking a stay at either Ladera Resort or Jade Mountain, both of which boast an open-air ambience in picturesque, oceanfront suites. Embrace the three-walled architectural design (and accompanying laid-back island lifestyle) in one of the utterly romantic seaside abodes offered by either hotel. Don’t worry about the potential lack of privacy—all of the properties in Soufriere are so tucked away within the tropical environs that walls hardly seem necessary. Why would you need them when you have such an idyllic view overlooking the sea?
Sugar Beach is another elegant resort that redefines Caribbean hospitality, with its 24-hour butler service and chilled champagne just waiting to be popped open beside your private poolside cottage. Though it’s difficult to leave such enticing accommodations, you should venture outside at least once to explore the island’s varied offerings. We suggest a chocolate tasting at the historic Hotel Chocolat and hiking in the foothills of the Pitons (and perhaps higher if you’re feeling ambitious.) Of course, if you’re content to watch the sun rise and set above the Caribbean Sea from your mountainous perch amongst the tropical rainforest, we certainly wouldn’t blame you one bit.
Antigua and Barbuda, Leeward Islands, Eastern Caribbean
For our final selection, we are headed to the Leeward Islands once more, to the hillside luxury that abounds throughout Antigua Island. Similar to Grenada, Antigua is also famous among yacht-owners and consummate travellers, who sail from the South of France in the summertime back to Antigua when the temperature drops. And what is it about Antigua that makes this island so impossible to resist?
Well, to put it in the simplest of terms, it’s a place where billionaires can go and pretend to live like dockhands, angling for a drink at Cloggy’s in English Harbour after a shift, or surfers, attempting to hang ten for sunbathers on the beach at Half Moon Bay. There’s a unique Antiguan blend of hyper-luxury and maximal laid-back island vibes that makes the island irresistible. Travellers can book a room at the sophisticated and elegant environs of Jumby Bay or Curtain Bluff, enjoying the seclusion of their surroundings before heading to the Sunday night barbeque at Shirley Heights, where the camaraderie is evident amongst locals and visitors alike. This sense of privacy and community in Antigua is unparalleled in many other islands around the world.
Antigua and Barbuda, also known as the Twin Islands, are a picturesque oasis for beach-lovers and wellness-seeking travellers alike. The crystal-clear turquoise waters, white-sand beaches and towering palm trees at Carlisle Bay are enough to provide even the most tormented of travellers a bit of internal relief. And active travellers should book an excursion with Adventure Antigua for some first-class boating and snorkelling in the legendary blue waters surrounding the island. Despite its luxury resorts and first-class hospitality, Antigua still has an old-school Caribbean vibe, it still feels quaint—and these authentic island vibes are reminiscent of what was once another secluded island getaway: Harbour Island.
Though Harbour Island is only 3.5 miles long, it has grown to occupy a far more substantial presence in the global imagination. This outer island of the Bahamian archipelago has become a magnet for status-conscious travellers. The formerly low-key beach shack, Sip Sip, is now immortalized in the opening scene of China Rich Girlfriend (Ken Kwan’s sequel to Crazy Rich Asians, of course.) So, visit Antigua while you still can, before it becomes swarmed by the rich and would-be famous. ◼