I'M ABOUT TO GO FOR THE RIDE OF MY LIFE. It's February, and I've been in the British Virgin Islands for five days with Trip Forman and Matt Nuzzo, founders of the Cape Hatteras, North Carolina–based Real Kiteboarding. The duo has recently teamed up with charter-yacht juggernaut the Moorings to offer a weeklong kiteboarding cruise in the BVIs. Their first official trip will be in December, but I'm on their shakedown sail, an informal preview that's part scouting mission, part Faustian flotilla. Within these hundreds of miles of Caribbean perfection—where warm and consistent trade winds swirl across deserted beaches and secluded bays—our aim is simple: Eat like royalty, drink like rock stars, and kite our asses off.

We've just dropped anchor near Eustatia, a small island opposite Necker, the private enclave of British billionaire Sir Richard Branson. The two sleek 50-foot sloops and one spacious 47-foot catamaran we've chartered are hauling kiteboarding equipment, surfboards, snorkeling gear, a barbecue grill, several pounds of bacon (Forman's favorite dish), and enough Mount Gay Rum to drown a whale. Last night, Forman, 38, plied me with far too many Manatinis, his homespun concoction of four parts rum, one part Cointreau, and a splash of lime. "Drink more than two," he warned, "and you'll be canceled." I did, and I'm still shaking off a hangover as we bounce across an aquamarine lagoon in our dinghy to Eustatia's southern shore. On a pearly-white beach, Forman helps me rig a 20-square-meter kite.

I'm a little nervous about holding down a mighty 20-meter. The largest kite in my quiver of four is only 17 meters, so the 20 seems like a monster, spanning 23 feet from wingtip to wingtip. But Nuzzo, 31, Real's teaching guru, assures me it's all a matter of technique. My problem, I tell him, is riding upwind—the single defining skill that, when mastered, graduates a beginner to intermediate. Nuzzo's upwind tip: "Just imagine you have a piece of coal between your butt cheeks and you have to squeeze it hard enough to turn it into a diamond."

Nice visualization. But if that's what it takes for me to get into the zone—when I become a perfectly balanced fulcrum, flying between water and sky—my butt cheeks are ready. Dialing in the right stance means a magical ride, which is what fuels my passion for the sport, drains my bank account, invades my sleep, and obsesses me by day. I keep a browser window open on my computer 24/7 to a Web site that tracks the wind at my local beach, New Road, in Delaware. If it breaks 12 knots, I'm there. My wife, Ashley—also an addict—and I have amassed a basementful of kites and boards and have road-tripped thousands of miles in search of the perfect breeze.

We're not alone. By some estimates, there are already 250,000 kiteboarders worldwide—and the sport is only eight years old. That may sound unimpressive next to the estimated 2.4 million global windsurfers, but the latter has had four decades to mature, and its popularity has been in a steady decline since the mid-nineties. (A fact that Forman and Nuzzo have heralded with their trademark bumper sticker: WINDSURFING HAS BEEN CANCELED.) Kitebeaches.com lists more than 2,000 kite launches around the world—from Argentina to Cambodia. A half-dozen magazines cater to the sport. A thriving gear industry churns out 80,000 kites annually, and, with the exception of Antarctica, there are kiteboarding schools on every continent.

On TV, you might see the pros whipping across the water at speeds surpassing 25 knots and launching wildly complex tricks 30 feet in the air, but kiteboarders are not just extreme-sport nutjobs. A swift learning curve—most beginners catch rides their first day on the water—and new, virtually foolproof safety systems are luring everyone from preteens to baby boomers. I regularly kite with a 73-year-old retired Air Force pilot who struts down the beach wearing a T-shirt that reads, OLD GUYS RULE. Senator John Kerry famously gets his summer fix on a kiteboard. Bruce Willis has reportedly been spotted shredding flatwater near his compound in the Turks and Caicos. Today, Richard Branson's twenty-something son, Sam, radios our boat from his dad's island. He wants to ride with us.

I glance toward Necker, wondering if the Bransons will show. But when it's windy, Forman doesn't like waiting around, so he launches my kite, and it charges full-throttle. I have five minutes before I'm too far out to return to the beach. OK: Coal... butt cheeks... squeeze... whoa, it works! The ass-clenching trick forces my hips forward and throws weight onto my heels, allowing me to lock in my board's edge and carve upwind. I slice through the chop while holding an arrow-straight tack across the lagoon. I'm in the zone.