Winter in Montauk can be a beautiful kind of quiet—but eventually the grey skies and freezing temps get the best of us, pushing everyone south in search of some vitamin D. For our family, that means making our annual pilgrimage to the island paradise known as Barbados.

My wife’s roots on the island run deep. Her family has been spending winters there since the 1970s. Originally from Cuba, her great-grandparents spent a season sailing the Caribbean in search of an island to call home, and when they reached Barbados, they fell in love and settled on a stunning little stretch of the West Coast. Most would argue that the West Coast is the most beautiful part of the island—and I wouldn’t disagree, but if you’re there to surf, the waves are better just about everywhere else...

If longboarding is your thing, the South Coast is paradise. The spot where we stay has clean, peeling lefts and a bay full of sea turtles. My wife claims it’s her favorite place on earth, and honestly, I get it. For something that packs more of a punch, there are a few spots up on the Northwest side that will definitely deliver when the conditions are right. But if you’re like any surfer visiting the island looking to get the heart rate up, you really came here for one wave and one wave only, and that means trekking across to the East Coast where things are sure to get a little more exciting. We're not out here trying to blow up anyone's spot, but... IYKYK.