Back when I was in the music industry, working festivals and performing as a DJ, travel became my passion. Visiting places like Playa del Carmen, Tulum, Miami, and various destinations in Latin America was exciting—and certainly helped me overcome my fear of airplanes—but it wasn’t until I started visiting the Caribbean islands that I truly fell in love.
One particular getaway to Aruba unlocked something in me—a desire to transform and be my best. With all that we have been through over the last year, I can’t wait to get back out there and return to so many of my favorite hotels and resorts that I have visited.
I’m most eager to start booking again, and we hope you will, too. Hopefully this selection will inspire you and add a little sunshine to your future.
A life of luxury awaits on the mocha latte beach at Silversands. The 43 suites and hillside and beach villas at this beloved resort are enveloped in the marvelous smells of the bountiful frangipani flowers and the spices from which this island draws its nickname, “The Spice Island.” The 100-meter infinity pool holds the distinction of being the longest in the Caribbean, and it is ideal for early morning lounging or staring at the sunset’s reflection (Grenada’s sunsets are the closest thing to heaven).
More interesting and especially fascinating is how the hotel subtly integrates its spaces throughout the northern end of the Grand Anse area with local houses, all wrapped up in the rainforest. The result is a splendid atmosphere and a Caribbean getaway unlike most others.
The Cliff Hotel—Negril, Jamaica
Chilling on your terrace, lounging in a hammock while sipping a Red Stripe, and enjoying the sounds of the waves charging the rocks—this is the life at the best all-suite hotel in Negril. In addition to a beautiful, expansive pool that is ideal for kicking back, catching some rays, and enjoying some frosty Marleys, The Cliff Hotel is also home to an incredible natural saltwater pool nestled in the rocky shore.
Honed for romance, Galley Bay is the Caribbean getaway everybody needs. It is so quiet that even at full capacity (barely the case) you won’t realize you’re not the only guests. There’s a patch of sand for everyone, even Giorgio Armani—he owns a villa on Galley Bay Heights, so you’re practically neighbors.
As a tribute to the artist Paul Gauguin, the South Pacific influence of the hotel is evident, and well assumed. Every room sits right on the sand, providing the incomparable sounds and sensations of the waves washing the sand. To top it all off, the food is delicious and the crafted cocktails are addictive. That’s Galley Bay life.
Guana Island—British Virgin Islands
What do you really need to say about a glorious private island experience set on more than 800 acres and boasting seven beaches? Probably that it only allows 35 guests, with just 18 rooms and villas, making it one of the Caribbean’s most exclusive experiences from beginning to end. This really is a tropical dream come true.
And while all dreams end, and everything washes away with the tides, these memories will forever remain with you just as your name remains in Guana Island guest book. Maybe in the very near future you will have the chance come back, or maybe not. But if you do, the courteous, friendly staff will be there, smiling, ready to make your dreams come true again.
Serenity at Coconut Bay—Saint Lucia
Your fellow passengers would be insanely jealous if they knew that while they’re circling Saint Lucia for an hour and a half, you’re already enjoying your private plunge pool after a five-minute direct transfer. At Serenity at Coconut Bay, the privacy is paramount and one of the resort’s primary rules.
Here, your backyard is your playground. Pack a light suitcase and bring your sexiest bikinis, because your principal activities will take place between your private beach cabana and your suite. And you will be spoiled—even your private butler will become your best friend.
Jumby Bay Island—Antigua
What makes Jumby Bay Island so special is that it all belongs to the homeowners, and they have their own palaces hidden among the palm trees (for example, check out the magnificent Lost Puffin). They help preserve the natural beauty of the island and keep life simple, as the sheep roam free, along with the odd tortoise and ducks. Exotic fruits and plants grow everywhere. You can even dine at the farm, or, if visiting on a Wednesday, pedal your way to a West Indian hangout at the pool grille, where you’ll be accompanied by steel pan sounds.
We can feel Antigua’s old-school charm while enjoying the sophisticated dining options, refreshing bars, warm Caribbean service, and irresistible suites. Managed by the Oetker collection, Jumby Bay is inarguably one of the best in the Lesser Antilles.
Round Hill Hotel and Villas—Montego Bay, Jamaica
When the rooms are designed by Ralph Lauren, it tells you everything you need to know about where you’re dropping your suitcases, right? Deeply rooted in Jamaican culture, everything about the way Round Hill Hotel and Villas operates is authentic yet distinct, and the result is a vacation experience that caters to the individual attitude and style of each guest.
As far as accommodations, the Grand Pineapple Villa Suite delivers beyond expectations. Each villa suite is housed within one of the 27 spacious private villas that are tucked into the hillside and overlook Round Hill Bay. You could end up in a romantic villa on the edge of the hillside, or you might stay in a secret agent treehouse hanging on the cliff in the jungle. It goes without saying that there is no wrong choice.
Casa de Campo—La Romana, Dominican Republic
This legendary hotel is spread across a generous 7,000 acres and boasts three championship golf courses, including Teeth of the Dog, which is considered by many to be the best in the Caribbean. Plush rooms and suites, in addition to complete villas overlooking the sparkling Caribbean Sea, are available for rent.
There are phenomenal culinary experiences to try and so much to do on-site and in the surrounding region, so be ready to get the most of your golf cart. Minitas Beach Club and Restaurant is also the perfect spot for watching the sunset. Simply put, Casa de Campo has very little competition in the Dominican Republic. Just ask Jennifer Lopez.
No, you didn’t make a wrong turn and end up in Bali. With its carved trees, thatched roof pavilions, Umbul-umbuls, and tribal statues, Laluna feels like it is worlds away, which is great when your goal is an incredible romantic getaway.
Fronting a fabulous beach, the huts of different washed-out colors seem like they have been painted in faux-fini. This hotel is one of the most unique in the region, if not the Caribbean and beyond.
Eclipse at Half Moon—Jamaica
What could please your partner-in-crime more than staying at the place where 007 himself, Roger Moore, once set a snake on fire for that classic scene in Live and Let Die?
Perhaps the recent opening of Eclipse, a brand-new beachfront hotel with luxurious oceanfront accommodations boasting incredible décor and details, from the lovely white shutters to the outdoor showers. Not to mention the “Tulumish” Spice and Hammock bar with its swings and classic Jamaican cuisine. This place is a treat for everyone from lobster freaks and famous jerk festins to equestrians and nature lovers.
Eclipse is a pure fantasy escapade surrounded by Jamaica’s incomparable natural beauty.
This hippest all-villa hotel in Antigua runs with 24-hour service and on-call rotating ambassadors. Each villa is equipped with outdoor patios, an infinity edge pool, and a wet bar with top shelf spirits, all curated by the in-house sommelier. Oh, and don’t forget the 500-count thread Egyptian linens in the beds. Guests might even discover turtles swimming and nesting nearby.
Michelin-starred Chef Marco Festini concocts tremendous Caribbean lobster and ravioli dishes at Lighthouse. Just ask your ambassador to put two on the side for you before you enjoy your favorite Reggae vinyl in the “secret lair” known as Chairman’s Lounge.
Nisbet Plantation Beach Club—Nevis
Steeped in history, Nisbet Plantation Beach Club seemingly never gets old, instead becoming more beautiful with each visit. The island’s only plantation hotel located right on the beach, this property is so quiet that it feels like your own little slice of heaven.
While all three of the on-site dining options offer something different (and delicious), don’t miss out on the weekly celebrations at Coconuts, where the rum punch will certainly have you feeling the Caribbean rhythm.
Excellence Oyster Bay—Montego Bay, Jamaica
Sometimes a name is just a name, but Excellence routinely strives to make guests expect the best of its resorts, from Playa Mujeres to this truly special property located in the heart of legendary Montego Bay. As soon as guests pass through the gates here, the modern style and attention to detail in the design become overwhelmingly evident.
With the festive layout of the resort’s amenities, restaurants, and lounges—not to mention the suites with their marble accents and private pools—there’s no denying Excellence Oyster Bay’s place among Jamaica’s finest. And believe us when we say that splurging for the Excellence Club is worth it, because the exclusivity makes it feel like you’re staying at a resort within a resort.
Still craving more? Rent one of the private villas directly on the sand and enjoy the best this island has to offer.
Hyatt Zilara Cap Cana—Dominican Republic
On stunning Juanillo Beach, you can spend your days in any number of ways: lounging in a sprawling infinity pool, practicing yoga by the water, or simply working on your tan. (We prefer all of the above, of course.) With a funky style and truly unique accents throughout, the accommodations provide positive vibes and views for days, while the hotel’s on-site dining options, including flavors of Tahiti at Brando’s and Indian cuisine at Journeys, are a must-try.
Or, if you’re looking to get a little more from your dining experience, take one of Hyatt Zilara Cap Cana’s daily cooking classes. They pair nicely with dance and Spanish classes, too. All in all, this place is high on energy and color, and it’s so much fun that you might forget to apply sunscreen between drinks.
Happiness is guaranteed for anyone who takes the dirt road leading to Hermitage Bay. Guests are rewarded upon arrival with fresh-squeezed mojitos, and the truly inspiring and original Bob Marley portraits signal your chill Caribbean break ahead.
With just 30 cottages, this resort has earned its reputation as a beacon of Antigua’s hospitality by enhancing every aspect of the guest experience. This is especially the case with the food.
Rosewood Little Dix Bay—Virgin Gorda, British Virgin Islands
As you make your grandiose arrival aboard the hotel’s catamaran from Tortola through Little Dix Bay, your butler will be waiting to transfer your baggage to your suite. Opened in 1964 by the visionary Laurence Rockefeller, this resort is a wonderworld. And despite the destruction caused by Hurricane Irma in 2016, Rosewood used its magic wand to restore and even revamp this property to its full glory.
While visiting Rosewood Little Dix Bay, enjoy the “beach drops” to a variety of hard-to-reach local spots, but especially the rocky caverns of The Baths. And be sure to indulge in Pavilion’s Trinidadian seafood pot with a nice wine from the restaurant’s extensive list. On a sunny day, under the “hairy” palapas, swimming in the crescent-shaped saltwater bath is tough to beat.
Calabash Cove—Saint Lucia
With enticing suites, dreamy ocean vistas, mahogany loungers, a swim-up bar, and plenty of Planter’s punch, you’ll definitely find your happy place at Calabash Cove. The infinity pool is a big selling point here and is, as they say, to die for. Factor in the beach and guests will wonder why they would stay anywhere else.
The Balinese-inspired waterfront cottages will make it difficult to leave them, but the amenities will snap you out of it. Especially the Windsong Restaurant, where you’ll feel as though you’re dining on the highest platform of a cruise ship with lights in distance.
Petit St. Vincent—St. Vincent and the Grenadines
Ready for your Pirates des Caraïbes vacation? Fly to Barbados, where you’ll be whisked aboard a private charter for a quick flight, ultimately boarding a boat that provides a blue watercolor spectacle until your arrival at this magical island.
White sand beaches, coral reefs, and lush greenery beckon visitors to Petit St. Vincent. One- or two-bedroom stone cottages are dispersed across various spots of the island, with some right on the beach, where guests will be greeted by bountiful marine life. Your mobile meditation app is not required for slowing your pace here, as you are always a mini-moke ride away from a Hawaiian lomi-lomi massage with four hands.
Spice Island Beach Resort—Grenada
Dreaming of soaking up the sun at a family-run, Six-Star Diamond Award recipient in Grenada? Spice Island Beach Resort is set right on Grand Anse Beach, the most beautiful slice of paradise on this off-the-radar island. Here, refined suites rest along the sand, allowing guests instant access to the stunning water while enjoying unparalleled amenities, including especially creative gastronomy.
Also boasting one of the most devoted staffs in the Caribbean, this resort is well-known for exceeding expectations. Janelle Hopkin, president and managing director of Spice Island Beach Resort, recently recalled to us the legacy her late father established and how she will keep it going.
“Sir Royston, my father, was a giant of a man,” she explains. “The warmth and personal touches of his legacy will remain embedded in the DNA of our resort’s highly acclaimed sense of casual, Caribbean chic. He was renowned for being a leader, a trailblazer and an innovator but for also remaining grounded in Caribbean hospitality—’Quintessentially Caribbean.’ It’s upon this amazing foundation that I will continue to build with the management and team, embracing the modern conveniences of the 21st century and firmly securing our position as a premier resort destination in Grenada and the wider region, while retaining the charm and personality that has made it famous.”
It is a no-brainer why loyal guests from around the world are so impatient when it comes to arriving at Maurice Bishop International Airport again. Us, too.
With unspoiled views of Long Bay Beach, this tropical castle owned by Geoffrey Fieger is very uniquely decorated with extensive Haitian art that you’ll fall in love with, quickly. From luxury suites to the penthouse, there’s an accommodation for everyone seeking a little piece of Caribbean elegance.
It is not costly to dream at the Quintessence Hotel; in fact, this is an ideal place to unwind and explore the shores of Anguilla. You can even rent the whole tropical grand mansion for the sake of making this a family adventure.