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How to fly first class on every trip: Travel hacking tips revealed

Ben Schlappig, 25-year-old master manipulator of frequent-flier programmes, is spending his VIP life airborne. Ben Wofford takes to the air with a hero of the secretive, obsessive subculture known as the Hobby

Reading Time:16 minutes
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Schlappig gets the first-class treatment. Photos: Ben Schlappig
Schlappig gets the first-class treatment. Photos: Ben Schlappig
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The boarding procedure has barely started at Chicago O'Hare airport and Ben Schlappig has already taken over the first-class cabin. It's Valentine's Day and, on Cathay Pacific Flight 807 bound for Hong Kong from the United States, he's passing out designer chocolates to a small swarm of giggling flight attendants. The six suites in this leather-bound playpen of faux mahogany and fresh-cut flowers comprise the inner sanctum of commercial flight that few ever witness. They're mostly empty now, save for two men in their 20s who seem even giddier than the flight attendants. The two stand to greet him. "This is so cool!" exclaims one, and soon Schlappig is ordering champagne for everyone.

This sort of thing happens to Schlappig nearly everywhere he goes. On this trip, his fans will witness Schlappig's latest mission: a weekend jaunt that will slingshoot him across East Asia - Hong Kong, Jakarta, Tokyo - and back to New York, in 69 hours. He'll rarely leave the airports and when he does he'll rest his head only in luxury hotels. With wide ears, Buddy Holly glasses and a shock of strawberry-blond hair, Schlappig resembles Ralphie from if he'd grown up to become a J.Crew model. Back beyond the curtain, in business class, a dozen jowly faces cast a stony gaze on the crescendos of laughter and spilled champagne - another spoiled trust-fund kid, they've judged, living off his parents' largesse. But Schlappig has a job. This is his job.

Schlappig, 25, is a hero to an elite group of obsessive fliers whose mission it is to outwit the airlines, self-styled competitors with a singular objective: fly for free, as much as they can, without getting caught. In the past 20 years, the internet has drawn together this strange band of savants with an odd mix of skills: the digital talent of a code writer, a lawyer's love affair with fine print, and a passion for airline bureaucracy. It's a whirring hive mind of IT whizzes, stats majors and aviation nerds.

Schlappig owes his small slice of fame to his blog, One Mile at a Time, a diary of a young man living the life of the world's most implausible airline ad. Posting as often as six times a day, he metes out meticulous counsel on the art of travel hacking - known in this world as the Hobby. It's not simply how-to tips that draw his fans, it's the vicarious thrill of Schlappig's non-stop-luxury life - one recent flight with a personal shower and butler service, or the time Schlappig was chauffeured across the tarmac in a Porsche. But his fans aren't just travel readers - they're gamers, and Schlappig is teaching them how to win.

“There’s a joke: I’m not heterosexual, I’m not homosexual, I’m aerosexual”

"I'm very fortunate in that I do what I love," says Schlappig, stretching out in an ergonomic armchair as we reach 30,000 feet and just before the mushroom consommé arrives. In the past year, since ditching the Seattle apartment he shared with his ex-boyfriend, he's flown more than 650,000km, enough to circumnavigate the globe 16 times. It's been 43 exhausting weeks since he slept in a bed that wasn't in a hotel, and he spends an average of six hours daily in the sky. He has a freewheeling itinerary, often planning his next destination upon hitting the airport. Yet for all his travel, it would be a mistake to call Schlappig a nomad. The moment that he whiffs the airless ambience of a pressurised cabin, he's home.

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