What the definition of a hip destination? It’s the place itself. It’s the people who go there — or the lack of people who go there. It’s the locals. It’s the culture. It’s the energy. It’s what draws people. The Caribbean is full of hip destinations. They’re not usually cruise destinations. They’re places that are for different crowds, they’re places that are under the radar and are kept that way. You’ll notice that many of these are surfing spots — that’s because often surfers have the best compasses for hip places, if they’re not making them hip by their very presence. These are the places that are connected with their environments, the places for people in the know. And now you’re one of them.
Cabarete, Dominican Republic
Really the top surf destination in the Caribbean, but it’s more than that — windsurfing, kitesurfing and a amazing collection of beach cafes and world-class eateries right on the sand. It’s the hippest place in the Dominican Republic and a popular destination for Europeans and young people. For a great stay, try the Millennium Resort and Spa.
Rincon, Puerto Rico
One of the Caribbean’s surfing capitals, this is Puerto Rico’s laid-back capital of cool, too. It’s a place apart, a secret getaway on the far west edge of Puerto Rico. If you want to be really hip, stay at the tony Horned Dorset Primavera boutique hotel past the edge of town.
St Barth
This isn’t under the radar, but St Barth has always been able to retain its hip factor. It’s not just because of the celebrities who come here — this island is full of trendy bars, high-level shopping and relaxed but elegant accommodations. For a reasonable, St Barth affordable on the beach, go for the Tom Beach hotel.
Port Antonio, Jamaica
This is one of Jamaica’s harder-to-reach destinations, and that’s afforded what is really a fishing village with an ultra-cool mystique, helped in large part by its collection of boutique hotels like Geejam and Trident (above).
Tulum, Mexico
Forget everything you think you know about the Mexican Caribbean. Tulum is the bohemian beach destination, the place that attracts artists and dreamers and those in search of a classic beach hideaway. Try the Hotel Nueva Vida de Ramon for your stay.
Cooper Island, British Virgin Islands
This private island is home to a single hotel, the Cooper Island Beach Club, but it’s carved out a niche in the British Virgin Islands as a young, cutting-edge hospitality center, attracting a healthy mix of locals, young people and sailors.
Bathsheba, Barbados
It may not be the Barbados you’re used to – there are strong waves, large boulders and rocks and its own little world. Yes, there are surfers here, but you don’t have to be one to enjoy the fascinating vibration. Head to the Atlantis hotel for the essence of Bathsheba cool.
La Trinité, Martinique
Set on the eastern Atlantic coast of the island, this is a funky, off-the-grid corner of Martinique. It’s of course popular with surfers, but the allure here is that it really feels like a closely-guarded secret. For the best views of the sea, try the Residence Oceane hotel.
Bequia, St Vincent and the Grenadines
When you think of hip in the Grenadines, you probably think of Mustique, which is one of the most exclusive places in all of the Caribbean. What makes tiny Bequia hip is everybody-is-welcome vibe — this is an artsy, friendly, eclectic island.
Roatan, Honduras
Honduras is one of the Caribbean’s on-the-cusp destinations, with a large number of expats and a smattering of eclectic, artful villages making for a rather unique vibe. Its low cost of living also makes for an unpretentious, relaxed place to visit. For an authentic stay in the Bay Islands, try Anthony’s Key Resort (above).
Terre de Haut, Guadeloupe
Some call it mini-St Barth, or at least St Barth as it was a few decades ago. While this retains the charm of a small French fishing village, it’s also a magnet for European travelers in search of a tucked-away paradise. There are art galleries, haute cuisine restaurants and an overwhelming sense that no one will have any idea where you are. For an affordable, beachfront stay, go to the LoBleu Hotel. Lô Bleu hotel right near the port.
Isla Holbox, Mexico
This place first became hip as a destination for whale sharks, and then the people followed. But not too many of them — there’s nary an automobile on the whole island, which is set off the coast of the Yucatan peninsula at the crossroads of the Gulf of Mexico and the Caribbean Sea. Stay at the Casa Las Tortugas (above).
Lac Bay, Bonaire
Bonaire isn’t a big destination to begin with, but its epicenter of hip (or should we say hipicenter?) is Lac Bay, home to the island’s best beaches, its windsurfing community and assorted beach shacks. For a great little beach stay, go to the Sorobon Beach Resort right on the sand (above).
Bocas del Toro, Panama
We’ve called the Undiscovered Caribbean in the past, and this enclave of islands off Panama’s Caribbean coast remains untouched by mass tourism. It’s an eccentric, maritime place that’s a destination as much for its natural beauty as the cast of characters it attracts.
Placencia, Belize
There’s a reason there are quite a few Western Caribbean places on this list — it’s because the whole sub-region has a burgeoning hip factor. Belize isn’t unknown, but Placencia is its wonderful little beach destination. With 12 miles of beach, great diving and an active, eco-conscious vibe. And it doesn’t get hipper than Francis Ford Coppola’s Turtle Inn boutique hotel (above).