There’s a peculiar joy to finding that hidden-away hotel, the one you haven’t heard of, the one without a brand but with a personality.
There’s a feeling you get when you discover a hotel for yourself — one that soon develops a need to find more like it.
And the Caribbean is filled with the kinds of under-the-radar properties that invite just this kind of exploration, character-filled properties with fully developed identities that have that x-factor, that certain indescribable quality that makes them, well, cool.
Our popular Cool List is back for its seventh annual edition with a list of 20 properties from across the Caribbean, all cool in their own way, all waiting for you to discover them for yourself.
Secret Bay, Dominica The signature boutique hotel in Dominica is back and better than ever, including its spectacular Zabuco honeymoon villas with their private pools. Local hotelier Gregor Nassief’s villa resort remains one of the ultimate experiences in the Caribbean, with marvelously personalized service, a surfeit of adventure options and, well, some of the most spectacularly designed rooms anywhere. It’s modern, it’s luxurious, it’s elegant but it’s also impossibly cool.
OLV: Fifty Five, Puerto Rico The hottest — and coolest — new hotel in the Caribbean is this impossibly stylish 26-room boutique hotel in San Juan’s hopping Condado district. The all-suite property is sister hotel to the renowned O:live Boutique Hotel, just steps away in Condado. Our favorite feature? The stunning two-tiered rooftop pool deck.
Island House, Nassau Far away from downtown Nassau and Paradise Island is one of the island’s best-kept secrets: the boutique Island House, an effortlessly chic outpost with an impressive range of amenities for a small hotel, from three eateries, a spa and even an on-site cinema.
A suite at Guana.
Guana Island, British Virgin Islands There’s a mysterious, intriguing, tantalizing quality to this private island in the British Virgin Islands, where its whitewashed cottages work in tandem with the stunning environment. This is Mecca for those who love the natural wonders of the region, for those in search of that all-too-hard-to-find quality: stillness.
Skylark, Jamaica The hottest new hotel in Negril in years is this, the colorful, breezy Skylark, with a pristine stretch of white sand, quirk, funky rooms and, perhaps most importantly, the first Caribbean outpost of New York institution Miss Lily’s, the energetic Jamaican eatery.
The beach in Marigot Bay.
Marigot Bay Resort, Saint Lucia This is another side of Saint Lucia, tucked away in the island’s most beautiful bay. It’s a true Saint Lucian experience: the food, the beach, the rum, the warmth of the people. And then there are the gorgeous rooms, most of which come with their own private outdoor jacuzzis.
The lobby at The Fred hotel in Frederiksted.
The Fred, St Croix It was a game-changer for St Croix when it debuted in 2017, and now the ultra-hip boutique is one of the US Virgin Islands’ halo hotels. An eclectic fusion of historic and contemporary, this adults-only getaway is a portal to Frederiksted, a town which is quickly becoming a hotspot in its own right.
Le Soleil d’Or, Cayman Islands Cayman Brac is its own world in the Cayman Islands, quiet and serene, an untouched gem in the Western Caribbean. And now it’s got a great place to stay on its resume, thanks to Le Soleil d’Or, the farm-to-table-focused guest house marked by sleek design.
Manapany, St Barth The newest addition to St Barth’s hotel scene is this Anse des Cayes retreat, a hotel that delivers the requisite St Barth luxury but does so in a refreshingly unpretentious, colorful and laid-back manner. The rooms are full of personality (especially the toes-in-the-sand options) and the spa is as good as it gets in the Caribbean.
LTC Beach Hotel St Martin If you love the Caribbean and haven’t been to Grand Case, well, it’s time to go. The beloved French Caribbean beach town has made a comeback, and that means the spectacular culinary offering, the quirky food shacks and the bustle have returned. That includes this tiny but chic offering in the heart of Grand Case Boulevard, with light but forward-thinking design and hard-to-match ocean views.
Anegada Beach Club Anegada has long been the frontier of the British Virgin Islands — and that’s certainly the overarching feeling at this exotic outpost that includes a stunning collection of “glamping” luxury tents perched on the dunes above Anegada’s strikingly white sand.
Belle Mont Farm, St Kitts It’s hard to find a way to categorize this boutique resort set on a working organic farm. But the most important thing is this: it’s one of the most beautiful hotels you’ll ever lay eyes upon in the Caribbean, from its neo-Caribbean stone great house and its gorgeous plunge-pool cottages.
Le Domaine des Bulles, Martinique Yes, this is a “bubble” hotel. Martinique’s funkiest hotel is a beautifully designed getaway, where you stay in clear bubbles that house remarkably well appointed suites — and even your own outdoor pools. It’s a once-in-a-lifetime kind of adventure, and it’s hard to get cooler than that.
The Admiral’s Inn and Gunpowder Suites in Antigua.
Admiral’s Inn and Gunpowder Suites Nelson’s Dockyard in Antigua remains something of a secret, a tucked away historic destination packed with beautifully rebuilt and restored 18th-century architecture. That includes the endlessly charming Admiral’s Inn, which includes a historic main house and a particularly pleasant infinity pool deck overlooking Admiral Nelson’s old stomping grounds.
Baoase Luxury Resort, Curacao We just can’t get enough of this luxury resort in Curacao that marries Bali-inspired design with the incessant energy of the Dutch Caribbean. The rooms are jaw-droppingly beautiful, with the food and the service to match.
Staniel Cay Yacht Club The Exumas are one of the most beautiful places on earth – but what they don’t tell you is that you simply have to be on a boat to explore them. That’s what makes this northern Exuma hotel so perfect — it isn’t just a wonderful place to stay — the rooms come with their own boats, too.
Casas del XVI, Dominican Republic It’s time to start thinking differently about the Dominican Republic. And that means Santo Domingo. The city long forgotten by most travelers is full of wonders, none better than the streets of the Colonial Zone. This luxury getaway is the best in the neighborhood, with lush design set in a series of 16th century buildings.
True Blue Bay Grenada is getting hotter as a destination — but if you want the authentic Grenadian experience, try this quirky, family-run boutique with its diverse collection of colorful rooms and villas — and an on-site waterfront eatery that’s one of the most popular spots on the island.
Atlantis Hotel, Barbados While it’s best known as a surf town, Bathsheba, Barbados is far more than that: it’s a rugged, raw, mystical place. And the historic Atlantis is a way to tap into that energy, with charming rooms, terrific food and a view toward the special spirit of the island’s east coast. This is a timeless hotel, in a Barbados you never knew existed.
The pool at the Thompson Playa del Carmen hotel beach house.
Thompson Playa del Carmen It’s amazing to see how Playa del Carmen has changed in recent years, and the ultra-hip Thompson has played a big role in that. This two-hotel complex, with an in-town and a beach component, has injected a new level of style and aesthetics to the city.