When the Outer Banks succumbs to winter’s grey skies, cold rain and renders surfing almost impossible, the prospect of spending the holiday season in warmer waters becomes a necessary escape. However, choosing a destination isn’t as easy as it sounds when constant wind is a must and the busiest travel days are afoot. There’s the standard safe bets: Cabarete, Brazil, Maui and so on, but this year I got an invite to explore somewhere different—Saint Martin—a locale in the Caribbean that isn’t your typical go-to windy destination.
During the first weeks of December I was blessed with everyday wind and waves on the northwest coast of Puerto Rico. But as my return date to the brutally cold East Coast quickly approached, my phone buzzed with an opportune text: “You know Saint Martin is only a 30-minute flight from Puerto Rico, you should come over for a week,” read an unforeseen message from Theo Demanez. A quick call to JetBlue canceled my return ticket and left my stay in Puerto Rico open ended until I sorted out the details. I like to remind myself that home will always be there, and you should never turn down the opportunity to explore the unknown.
Heading to Saint Martin I knew a few things and little else: It’s famous for its dangerously short runway, its easterly trade winds tick with the rhythm of clockwork and the flight from Puerto Rico is only a 30-minute island hop . . . or so it should be. My last minute booking habits coincided with the holiday masses and forced me onto a connecting flight through New York. The tension of a million Christmas vacationers in play and the short blasts of arctic atmosphere felt through momentary gaps in the jetways was enough to silence my annoyance with my itinerary and really made me appreciate a speedy, if not immediate return to the Caribbean.
When discovering any new place for the first time it’s usually at odds with what I imagined in my mind—not necessarily better or worse—but always different. Perhaps this is one of the things that allows me to enjoy my continuous pursuit of travel; the pure curiosity of how life can be so diverse throughout the world, to such a degree that I’m continually amazed by the substantial contrasts in neighboring islands. When I pictured Saint Martin, I envisioned a stereotypical Caribbean destination: flat turquoise waters, minimal winds and expansive white sandy beaches chocked full of tourists. Yet, what I found with the help of Theo, my local tour guide, was a place amazingly rich in culture and riding conditions. The moment I landed we were already discussing the week’s plans. While Theo had talked up his local beaches, the young buck was eager to take his family’s boat and head north to Dog Island for some exploring.
The islands that make up the Caribbean are a colonial hodgepodge of imperialist power struggles. There are three and a half French islands in the Caribbean that form part of the Lesser Antilles. Saint Barth’s and Saint Martin are considered the northern French islands with Guadeloupe and Martinique to the south, separated by Dominica and a few other islands such as Saint John’s, Antigua and Barbuda. With the French, Dutch and English warring for territory in the New World and unable to settle, Saint Martin has the unique distinction of being divided in half by controlling powers. Dating back to the 17th century when a line was drawn following a conflict with the Dutch, today the island remains split: Saint Martin is the French side and Saint Maarten is Dutch.
Dog Island is only a few hours sail from Saint Martin and much closer than any of the other French islands, but as I came to find out, it’s a marine preserve park off of Anguilla which falls under the British Commonwealth. Luckily, I still had my passport with me to navigate through this complex amalgamation of overseas territories.
With cloudy skies above and steady, warm wind at our backs, we came to anchor on Dog Island in just short of three hours. We raced to shore in a dingy piled so full of gear it nearly spilled over the sides. In contagious eagerness to ride in a remote paradise, anyone who didn’t fit in the skiff ’s first trip jumped overboard and swam ashore instead of waiting for the second landing party. We rode all day long with Theo’s family and friends in the lee of Dog Island. With its long sandy beach and stretches of water smooth as a sheet of glass, Dog Island proved to be an expedition worth taking.
Around 3pm and after hours on the water, we set sail back to Saint Martin for New Year’s jubilations. With the building wind we were able to quickly chart a course to the south aiming for home, but as soon as we rounded the corner of Anguilla our 38-foot catamaran stopped dead in its tracks against a relentless headwind. With only a few miles to go, we motored a measly 3.7 knots for the next couple of hours, battering our way amidst inexorable winds and choppy seas. Just as the sun began to set, it was clear that none of us would have the energy for the New Year’s festivities back in Saint Martin, but watching the sun go down on the last evening of the year while at sail and after a long day on the water is a tradeoff I’d make for fireworks anytime.
The next few days back in Saint Martin were spent keeping up with Theo on a hyperactive tour of all the local spots. Most people, me included, are totally content kiting for a few hours a day and then filling out the remainder of their vacation with some casual exploration and a little R&R, but this is not the case when you stay with Theo. Every morning, 6:30am alarms were set and religiously observed while our sessions went for as long as the sun would stay in the sky. Much like my younger self, Theo has endless energy and focuses it all towards being in the water. Whether it’s windsurfing, surfing, standup, or kiting on a foil, surfboard or twin tip, Theo is hardwired to wring out every ounce of fun each day has to offer.
Theo is not so much a mutant, but a product of his environment. He’s got a young, wiry frame that’s quickly filling into the physique of a dedicated waterman. With an incredible amount of natural talent and despite not having a driver’s license, Theo can pick up just about any board and put it to use with world-class finesse. Our day would start with a few minutes bike ride to Orient Bay where the Demanez family owns and operates a kite school and Vela Kitesurf destination. We’d check the wind and then head into town to grab some food at the local bakery. Right out front of the lesson center is one of the best spots on the island to ride; protected by Green Cay and a reef, Orient Bay offers everything from small waves to flat water and fun kickers.
On the light wind days we’d explore the whole area on foils, and when the trades kicked in, we’d head upwind and around the corner to Embouchure Bay to ride some waves, or just stay right behind Green Cay Island to ride flat water. The island’s topography is unique; its many small peaks descend into a coastline that harbors hidden coves and offers so many riding spots that we could only begin to scratch the surface within the week that I was there. As we explored the jagged and curving coastline, Theo talked of how, with just the right swell direction, Saint Martin can offer high quality, undocumented surf.
As we neared the end of my visit, the forecast showed promise of a new swell arriving on the last day of my stay. Four feet at 16 seconds out of the ENE was Theo’s formula for a head high wave at his favorite spot, just 15 minutes from his house in Orient Bay. While Saint Martin sits directly south of Anguilla, it has a relatively small swell window, but it’s exposed enough where, with the right angle, swell can still find its way to Saint Martin’s beaches. While it’s not known for it’s endless surf breaks like those of Puerto Rico and other Caribbean islands, watching a good forecast line up for Saint Martin makes it all that much more exciting.
Our eyes were on the forecast all week long and when it finally arrived, it also marked the bittersweet proposition of my last few hours on the island. The night before my parting flight, I could hear the rumble of waves in the distance. Theo woke me up extra early the next morning and we eagerly drove out on a dirt road that ended near the island’s garbage dump to a place that Theo called ‘Wilderness.’ We parked the car and ran carefully on foot for the next 15 minutes across a rocky shoreline until we finally caught a glimpse around the corner of the cliff to view an ocean in its changed state. To my surprise a satisfying chest to head high wave rolled through and broke over the reef.
My bags were already packed for the airport but we rushed back to Theo’s house where I pulled my 12m Drifter out of the bag, rammed fins back into my board and rallied to make the most of the last few hours I had left on the island. We launched just down the way from Theo’s house on a pretty tight, rocky shoreline at the base of the hill that doubles as the local paragliding spot. With shallow, sharp reef and straight onshore wind, Theo and I worked our way offshore with care not to knock our fins out on our way. We rode around a small headland to where I could see the stretch of deserted cobblestone beach along with the same perfect right-hand peeler we had spotted from land earlier that morning.
With not a road or a person in sight, it truly was the ‘Wilderness.’ If the wind died or if we had an equipment malfunction, the trek out of this spot would be exhausting, and there’d be no chance that I would make my flight. But since it never gets easier to turn down opportunities, I rounded the corner and dropped in.
Back upwind with our kites wrapped up, we had scored one of the best sessions of the week within just a few hours of my flight. A small part of me was open to a good stranding; missing my plane would make for a good excuse to stay for the second day of the swell, but that was not how this adventure played out. With no time to shower, I heaped a pile of wet gear into my bag and rushed to the airport. When I stepped off the plane and into the gridlocked immigration line of Miami’s bustling airport, I looked down at my feet still covered in sand—the last reminder of my week with Theo on Saint Martin—and smiled.