It’s often been said that if you have to ask how much something costs, you can’t afford it. The same is true of cool — if you have to ask why a place is cool, you’re never going to get it. That’s where this list comes in — the Caribbean’s coolest hotels for 2016, the places that ooze character, personality and, well, cool. These are our favorite places to stay right now in the Caribbean.
Secret Bay, Dominica
This hotel is comprised of treehouse-style bungalows and large, state-of-the-art villas, with the latter boasting their own private plunge pools. Everything here is high-tech and high-luxury — and you can have every meal served right on the deck of your villa.
JW Marriott Santo Domingo
The star of the show here is definitely the Winston Grill and Patio, which has a spectacular glass floor 101 feet over the capital Winston Churchill avenue. But the ultra-modern, amenity-full rooms are superb, too.
O:live, Puerto Rico
This hotel is a work of art — and the coolest hotel in all of Puerto Rico. The design here is eclectic but elegant, all the way to the stunning rooftop bar with views of the Condado lagoon.
Cooper Island Beach Club, British Virgin Islands
We always like to say that the coolest hotels are always full of more than one story. Here, that’s everything from the solar panels on the roofs to a world-class rum bar and a friendly, energetic staff. Not to mention that the beach is a happening spot for cruisers.
Karibuni Lodge, St Martin
This is cool because it’s two places for the price of one — a hillside lodge in St Martin with hip rooms and a private beach bar on the offshore islet called Pinel Island.
Four Seasons Resort Nevis
Embracing the local community is cool. And the luxurious Four Seasons Nevis pulls it off, combining the quintessential luxury experience with an unmistakably Nevisian flavor.
South Point Antigua
Antigua’s newest hotel is a crisp, sleek boutique right on the water in Falmouth Harbour, right in the center of one of the Caribbean’s megayacht hubs. But it’s an oasis, with large rooms and a great little patch of sand.
Lobleu, Guadeloupe
This is a no-frills hotel, affordable and simple, but it’s overflowing with character, set on the beach on the charming little French Caribbean island of Terre de Haut. It’s like a hotel from a book — a book you want to be in.
Suite Villa, Martinique
This isn’t just a cool hotel — it’s a work of art in itself. Proprietor and art lover Gilles Duplan has created a masterpiece in the hills above Trois-Ilets in Martinique — from the furniture to the dozens of paintings adorning the walls.
Hotel Chocolat, St Lucia
It’s located on a working cacao plantation and it’s got an infinity pool overlooking the Pitons. Do you need to know anything else? The rooms are eco-chic (with indoor-outdoor showers) and the food is simply spectacular.
The House, Barbados
This adults-only 34-suite hotel on the Platinum Coast has a library, a spa, a lovely stretch of beach and a mix of old and new Barbados. And the food comes from the adjacent Daphne’s restaurant, one of the island’s best.
Palm Island, Grenadines
This is castaway-chic, an impossibly beautiful white-sand private island in the middle of the Grenadines. The all-inclusive resort is cool in its simplicity, which maximizes the natural environment.
Baoase Luxury Resort, Curacao
This 23-room-and-suite boutique hotel is far and away the coolest hotel in Curacao, with a fascinating mix of Caribbean and Asian influences, with high-level food and a diverse room product. While it’s small, the beachfront area is large, offering all the zen you’ll ever need thanks to clever planning.
Laluna, Grenada
Grenada’s signature boutique hotel has 16 cottages, with a mix of myriad design styles. This is a hotel that also emphasizes wellness, with a strong spa and yoga focus.
Bucuti & Tara Beach Resorts, Aruba
Aruba’s coolest and best hotel is upscale without being pretentious, incredibly eco-friendly and set on the most beautiful stretch of beach on the island. This is a hotel that is religious about detail, even down to the air quality, something you rarely notice inside a hotel.
Sorobon Beach Resort, Bonaire
This is the best beach resort in Bonaire, set on beautiful Lac Bay. The highlight is that the bungalows here are right on the sand, not set back — that means you’re thrown right into the beach life.
Blancaneaux Lodge, Belize
The reason Francis Ford Coppola chose this place is because it was so cool before there was even a hotel. Now, it’s perhaps the ultimate Caribbean jungalow, with thatched roofs, Guatemalan-inspired decor and the luxury of being in touch with pure nature — without losing the essentials.
Tom Beach Hotel, St Barth
This is the essence of St Barth cool, without the pretentiousness. This 12-room boutique is set on one of the best beaches in St Barth, St Jean, and a hip, playful atmosphere. It’s just a fun place.
Hermitage Bay, Antigua
Whether you’re in the hillside or the beachfront cottages at this Antigua luxury outpost, you’ll be assured of one thing: a show-stopping room and an incredible view. The best part? It’s an all-inclusive — just not the kind you’re used to.
Southern Cross Club, Little Cayman
Little Cayman is cool in its own right, thanks to less than 200 people and some of the Caribbean’s most incredible diving, and this hotel takes directly to the soul of the island.
Thompson Playa del Carmen, Mexico
We’re big fans of Playa del Carmen’s Quinta Avenida, and the street now has a hotel to live up to its hype, the ultra-hip Thompson, also home to the first Mexico outpost of New York city eatery Catch.
Meridian Club, Turks and Caicos
This is a hideaway, pure and simple, a place to detox and connect with one of the Caribbean’s best white-sand beaches on an 800-acre private island.
Staniel Cay Yacht Club, Exumas
This is on an island away from an island, the beautiful little island called Staniel Cay. And if you’re staying here, there’s nowhere better than the Staniel Cay Yacht Club, a bungalow hotel that’s the essence of the Exumas.
Graycliff, Bahamas
From the third-largest wine cellar in the world to its own cigar factory to a selection of rare cognacs to the Brazilian churrascaria to the chocolate factory… you get the picture. Enrico Garzaroli’s Graycliff boutique hotel is, simply, a portal to the good life.
Queen’s Gardens Resort, Saba
This boutique resort high above Saba is, well, the best reason to visit Saba. Every room has its own three-walled jacuzzi, the service is terrific and the restaurant is one of the Caribbean’s best. A hidden Caribbean gem.