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.