Meet the Guys Gaming Luxury Travel on an Economy Budget

I’m going to take my shower in the sky, which is amazing,” says Brian Kelly. “And the caviar will be nice. And the Dom.” Over breakfast at the Belle Époque–style Excelsior Hotel Gallia in Milan in August, Kelly is discussing his upcoming first-class flight to New York on Emirates—using Alaska Airlines frequent-flyer miles—and his life devoted to gaming the world of luxury travel. The 32-year-old New York native runs The Points Guy, a website that teaches how to maximize airline- and hotel-loyalty programs for high-end travel—shower, champagne, and caviar included. “I have the best job in the world,” he says.

Kelly is part of a growing community of elite travelers who rack up hotel points and airline miles and spend their time hunting for regulation loopholes, taking advantage of errors in published fares, and going the extra mile to manufacture spending (see below) on frequent-flyer-point-accruing credit cards. “You don’t have to rob the bank to live life a lot better than you would if you had to pay for it,” Kelly says. “There’s always a way to maximize.” Like Frank Abagnale from Catch Me if You Can, some travelers even go as far as flirting with deception.

This elite community includes everyone from young professionals to students to retirees. Some are aviation savants who thrive on the fine print and bureaucracy. Some are jet-setters who revel in the high life and treat the game more like The Game, the pickup-artist bible. “Smart people are attracted to this ‘hobby’ because it’s like doing a crossword puzzle,” Kelly says. Or counting cards at a casino, day-trading on a laptop, or meticulously programming computer code.

Ever since major airlines started issuing frequent-flyer miles in the early eighties, savvy travelers have been searching for creative ways to accumulate them. But if the hobby had a “big bang” moment, it was likely in 1995 when an aviation fanatic named Randy Petersen launched FlyerTalk.com, an online community that now claims more than 600,000 members. And their tactics are legion. For years, hobbyists would buy dollar coins from the U.S. Mint on credit cards that award points, hiring trucks to lug the coins (up to tens of thousands) to the bank and then depositing them to pay the balance. (The Mint put a stop to the practice in 2011.) In 1999, David Phillips bought more than $3,000 worth of Healthy Choice pudding in order to redeem more than a million miles. He’s still reaping the benefits. Two years later, a miles-obsessed entrepreneur named Steve Belkin spotted $8 fares between two cities in northern Thailand and hired locals to fly up to five round-trips a day for six weeks, amassing miles. After three weeks, the DEA came calling, thinking it had caught the stupidest drug runner in the world. As Gary Leff, who works with Belkin at BookYourAward.com and writes the View From the Wing blog, explains, “If there’s a good deal, you might as well find a way to really scale it.”

Mistake fares are Leff’s favorite. The 41-year-old once flew to Italy when a $3,300 business-class fare on Alitalia was priced at $33.00. On another occasion, Le Méridien hotel in Khao Lak, Thailand, published rates in Ugandan shillings instead of U.S. dollars, so an oceanfront villa with a private pool was priced at just 60 cents a night. The hotel honored it at a marginally higher $33 a night, including tax and breakfast. Leff stayed for a week.

Even as airlines squeeze economy class, they’re upping the ante in business and first. A first-class ticket on Lufthansa out of Frankfurt gets you driven directly to the plane in a Porsche or a Mercedes-Benz. At Suvarnabhumi Airport in Bangkok, Thai Airways takes you from check-in to boarding in a golf cart, with a stop at the lounge for an hour-long full-body massage. Singapore Airlines has onboard suites with sliding doors, window blinds, and standalone beds seemingly designed to facilitate membership in the mile-high club. Etihad Airways has introduced First Apartments, complete with a chef who caters to your culinary whims. Emirates has an onboard shower and bar. “It’s not often that you get to drunk-text people from a shower on a plane while drinking champagne,” says Ben Schlappig, a 25-year-old from Florida who runs a travel-points booking service and blogs at One Mile at a Time. Schlappig recently spent a year living exclusively in hotels in his pursuit of the hobby.

There are also ways to get what you want when you’re already on the ground—the art of the upgrade. This is where Justin Ross Lee, a 32-year-old New York socialite, excels. Lee describes himself as many things—haberdasher, life enthusiast, founder of Pretentious Pocket pocket squares. But above all, he’s a luxury-travel opportunist. “If you want an upgrade, do not ask for an upgrade. The same way if you walk into a bar and want to have sex with the most attractive woman, don’t walk up to her and say, ‘I want to have sex with you,’ ” he says.

Instead, Lee advocates printing fake business cards to get corporate hotel rates or lighting matches in hotel rooms and complaining that someone smoked there for an upgrade. He once brought a ziplock bag of broken glass to sprinkle on the hotel-room carpet (he later confessed). His standby line, though, is that the room didn’t live up to expectations. Recently, he got upgraded to the $12,000-plus-a-night Governor’s Suite at the Park Hyatt, the hotel made famous in Lost in Translation. “What was my complaint? I couldn’t see Mt. Fuji, and the website said they had views of Mt. Fuji. There needs to be an asterisk saying ‘weather permitting,’ ” he says. “I told them it was my honeymoon. My entire year is a honeymoon, so how can it be false?”

All the gurus agree that there is no black-and-white code of ethics to the game—it’s personal—and Lee freely admits that he is further into the gray than most. “What is okay in travel and in taking advantage of hotels and airlines and loyalty programs? When you’re at a hotel and you pass a housekeeping cart, you take a soap. That’s okay. What if you take two soaps? That’s fine. What if you take 10 soaps? What if you roll the entire fucking cart into your room?” Lee asks unapologetically. “My travel is paid for by everyone else who doesn’t know how to play the game.”

“It’s a far from comfortable relationship,” travel analyst Henry Harteveldt says of the airlines and bloggers. While some hobbyists explain how to cheat airlines, others are actually benefiting the industry. “There is this awkward business relationship where the blogger may be generating a large number of card sign-ups, which bring the airlines money.” (For their part, bloggers can make over six figures in finder’s fees from the credit-card companies themselves.)

Increasingly, as the community has grown and tricks of the trade have proliferated, a rift has developed. Some view Lee and his ilk as scam artists besmirching the hobbyists’ collective good name. Others resent guys like Kelly for compromising the community’s closely held secrets. “Many of them hate me,” Kelly admits. “I’ve taken our game, so to speak, and I’ve taken it public, which they interpret as less for them. We’ve doubled in size every year because it is sustainable for everyone to play this game.”

In 2005, The Economist valued the global stock of frequent-flyer miles at more than $700 billion, and the airline industry has begun to fight back: Earlier this year, in an attempt to curb “mileage running,” Delta and United switched to systems that award points based on money spent rather than miles accrued. (Delta declined to comment; United hadn’t responded by press time.)

After breakfast at the hotel, Kelly and I head out to see Expo Milano 2015, a massive international fair. We’re greeted by our personal tour guide, bypassing several city blocks’ worth of people waiting in line. Kelly is getting the red-carpet treatment because he booked Etihad’s first-ever Residence flight out of America, which will depart JFK for Abu Dhabi on December 1, for $33,000—though he will get at least $6,000 back through points and status matches. “I paid cash,” he says. “But it’s a business expense—the most incredible experience in the sky.” The Residence is an onboard apartment with a private bathroom and shower, and Kelly booked his ticket the morning the new flight was announced. Ten minutes later, he got a call from Abu Dhabi welcoming him. He e-mailed to say that his preferred drink is Double Cross, a seven-times-distilled Slovakian vodka. Within 24 hours, Etihad e-mailed back: It would be chilled and waiting on his flight. “The whole experience was surreal,” Kelly says.

Kelly admits to growing somewhat spoiled by the comforts of luxury, but he’s still looking forward to the next big upgrade. As for that pesky gray area of mistake fares and maximizing points, Kelly doesn’t worry much about it. “It’s amazing to me how many people stick up for these billion-dollar airlines that exist to screw consumers, and when it’s time for the consumers to do something slightly in their favor, it’s like: ‘How dare they? These poor airlines,’ ” he says. “The airlines are making billions of dollars—it’s okay.”

STRATEGIES FOR GAMING THE TRAVEL SYSTEM

Apology Vouchers
Coupons offered by airlines if a passenger notes anything broken or otherwise nonfunctioning on a flight.

Flight Bumping
The practice of volunteering to take a different flight when one flight has been overbooked in exchange for a free ride, a generous voucher, or both.

Fuel Dumping
Booking technique that confuses the price algorithm to deduct the cost of fuel from a ticket, often reducing the total cost.

Hidden-City Ticketing
Making the layover on your flight the final destination. Essentially, booking a flight from point A to point C but getting off at point B. This is often cheaper than booking direct flights.

Manufacture Spending
When hobbyists use airline-affiliated credit cards to purchase what amounts to cash, like gift cards—earning miles in the process—then liquidating the purchases to pay off the cards.

Mileage Running
Constantly flying on steeply discounted flights in order to accrue frequent-flyer miles.

From the November 2015 issue.