A Travel Points Hacker Spills His Secrets

This is part of a special series, Indulgence, which explores extravagant living in a time of restraint. It’s also in the September 2021 VICE magazine issue. Subscribe here. 

For a small but passionate few, accruing travel points isn’t just a minor credit card bonus. To dedicated travel hackers—who hunt for mistake fares or meticulously track numerous credit cards—racking up points and miles to put toward extravagant trips can be an engrossing way of life.

When the pandemic hit in 2020, that came to an abrupt halt. While Americans continued to earn about $6.8 billion worth of mileage points, and many hotel and airline loyalty programs extended expiration dates to protect consumers’ hard-earned rewards, travel hackers had to resign themselves to a much more grounded lifestyle. Now, with vaccinations widely available in the U.S. and international borders reopening, they are back on the move. 

One such traveler is Henri Fitzmaurice, 23, who’s both prolific and proficient at racking up points and miles. Had COVID-19 not hit, Fitzmaurice—who graduated from a conservatory with a BFA in drama during the pandemic—had planned to spend last summer in Central America and Africa before pursuing a career in the entertainment industry. Instead, he’s been investing in stocks. In early April, as soon as he was fully vaxxed, Fitzmaurice flew from Los Angeles to Peru, and has barely stopped moving since. Over the past few months, he’s amassed more than 400,000 points and miles (and used 280,000 of them), boarded 22 flights, and crossed into five continents—all of it at a steep discount enabled by his uncommonly complicated spreadsheets. 

“Most people just assume I won the lotto or have heaps of generational wealth,” says Fitzmaurice. “I’d trade points for either.” 

APRIL 10, 2021 • LIMA, PERU

Ever since I was in high school, I’ve wanted to see Machu Picchu. When I found a good mileage fare for business class on American Airlines—cheaper than a therapy session—I bought my first post-vax trip. After long flight delays, I landed in Lima around 2:30 a.m. Within minutes of leaving the airport, my driver was pulled over and had to show a special ID because it was past curfew. The officer then looked in the back and saw that I was this six-foot-seven-inch white guy who was clearly going to a Marriott. We were soon on our way. 

When I got to the hotel, the person at the front desk told me they had upgraded my room because of my Amex number, which gives me status with the hotel. While going up the elevator, the doors opened on a floor that was clearly reserved for people who had been traveling in certain countries and were required to quarantine. It looked like a pseudo hospital: There were nurses and stations, and notes and numbers taped to every door. When I opened the door to my top-floor room and felt the fresh midnight air from the cracked window, I instantly started bawling. The kind of hard-cry-ugly-heave that had been pent up over 13 months of national tragedy, communal isolation, and pandemic disappointment.

APRIL 17, 2021 • MACHU PICCHU, PERU

After a week in Lima, I traveled to Aguas Calientes, the town that sits at the base of Machu Picchu. At the train station, I actually got picked up by the guide I had found through GetYourGuide, who was going to show me Machu Picchu the following day. (I think I dropped $60 or $80 for the tour, which I bought using Rakuten, a shopping portal that gives you rewards.) It was clear that I was going to be the only person in the tour group, and the guide and I made a plan for him to pick me up early the next morning.

Machu Picchu was amazing. After a year of low foot traffic from tourists, there had been so much plant regrowth. The grass was so lush, and there were hundreds of llamas freely roaming, which my guide said was new for them too. After the tour, I asked my guide about lunch, which he didn’t initially realize was an invitation. He eventually took me to the restaurant he goes to the most, which overlooked this incredible river and mountain. We ordered pisco sours, and he told me he’s been giving tours full-time for five years, and like so many people in their 20s, he had to move home during COVID. He was like, “Man, I’ve just been selling eggs at the farmers’ market for the last eight months, I feel like a total loser.” And I was like, “Dude, I literally just graduated college and my industry shut down, I feel like a loser. We’re all in this misery together.” 

MAY 12, 2021 • LUXOR, EGYPT

Hilton hotels have particularly low redemption rates in Egypt and Turkey, meaning they don’t require a lot of points to stay—as low as 10,000 points a night. So, while in Peru, I decided I wanted to look into taking a “Hilton tour” because I didn’t want to spend another $1,300 on my LA sublet that I hated. I ended up booking a flight from LA to Egypt on Turkish Air, and it cost me zero dollars to add a free stopover in Istanbul. I also booked four different Hiltons, staying five nights at each. If you book four awards nights at the same Hilton, you get the fifth free, so might as well make it five. And if you have Hilton status, you get a complimentary breakfast, which saves me a lot of money. If I eat a huge breakfast, I can usually get away with small bites until dinner. 

After a few days in Cairo, during which I saw the pyramids, I headed to Luxor, a city I’ve always wanted to visit. It has an incredible hotel on the Nile, and I also wanted to go hot air ballooning, which I was supposed to do last summer in Kenya. On Viator, I found a trip that cost about $27, and because I was using a card that got travel points, I got about $10 in travel credit. I have over 12 credit cards open at any given time (currently 14), and I know exactly which one to use for best earnings when shopping. I keep careful track in an Excel spreadsheet, and always pay off my balances in full so I don’t accrue interest. 

At 4 a.m. on May 12, a van picked up me and other tourists, after which we took a quick boat ride across the Nile to get to the launch site in this massive open field. We were the first flight of the day. As the sun was peeking out, we got photos of the banana fields below. And then suddenly, we started to hear all these little wails and screams, and all these kids—some on bicycles, some running as fast as they could—were waving. When we landed, 80 or so kids came rushing toward us, and they started grabbing my hands and asking for selfies. To have experienced a whole trip’s worth of memories and physical interaction in just two and a half hours on a weekday before I had even had a cup of coffee was sensational and completely overwhelming at the same time.

MAY 21, 2021 • ISTANBUL, TURKEY

I started hacking points and miles when I was 18, and I’ve been to over 45 countries in the past four years since, nearly solely on points. Right before coronavirus hit, I had an amazing year of travel. In 2019, I studied abroad in Barcelona, a location I picked because it had the cheapest airport in Europe. I went away almost every weekend—to Morocco, Poland, Ukraine, and others. It was during this time that I first visited Istanbul, using a free stopover from Turkish Air, and it’s now borderline one of my favorite cities. 

I had been in Istanbul for a day or two when I realized I hadn’t journaled, and I wanted to find a place where I could sit down and write. I came upon this terraced restaurant on a hill, where I grabbed a seat outdoors and ordered a kebab and a Long Island iced tea. I eventually ended up sitting with this older gay couple from Virginia. They were browsing Zillow and marveling at how they could afford to live in a new two-bedroom condo in downtown Istanbul for the price of just one of their Social Security checks. Finding queer people who are elderly is sort of a rarity, and it was really cool to see a couple who had been together for 30 years, had children and grandchildren, enjoyed each other, and were in Turkey to find their little pied-à-terre. I’m not sure I touched my food once that night. 

MAY 24, 2021 • TBILISI, GEORGIA

While I had a direct flight from Istanbul to Los Angeles, and I had to be back in California soon for a family trip to San Diego, I realized I had a few extra days to kill between the two. So, toward the end of my stay in Istanbul, I started looking for good deals on Google Flights and travel sites like AwardHacker. When nothing was really cutting it, in terms of a steal, I found a $40 flight on Turkish Air to Tbilisi, and I earned miles for it. I’m not big on spending actual money, but one of the most paramount things about traveling on points and miles is learning when not to use them on a purchase. At the beginning of post-vax traveling, the biggest out-of-pocket cost for me was COVID tests.

I ended up booking an Airbnb experience, which I had never done before, for a wine tasting in downtown Tbilisi. I was greeted by this Russian sommelier who had moved to Georgia a few years ago and spoke absolutely no English, and her best friend, who was also Russian, but who knew a little bit of English and served as her professional translator (using an app). It was just $10 for at least six half-pours of wine, and then they came out with cheeses, Georgian breads, and all these oils to try. I asked them to please sit with me—that there was too much cheese for one. At the end of it, the translator told me she’s this world-class poker player who goes to Las Vegas every year and makes her year’s salary in two weeks. It was crazy.

JUNE 5, 2021 • SANTO DOMINGO, DOMINICAN REPUBLIC

After my family trip in San Diego, I drove to Los Angeles to move into this new sublet that turned out to be totally not legit. When the cheapest nearby hotel I could find cost $130 a night, I asked a friend if I could sleep on their couch. There, I started looking into flights, and by midafternoon the next day, I found one to the Dominican Republic, and I bought a really cheap cash fare. I used an upgrade certificate, and I ended up getting a first-class flight with a lie-flat bed, mimosas, and a meal—all for less than what I could have found in the sticks of LA. I took the red-eye that night, and the next morning, I checked into this gorgeous $40-a-night Airbnb in a highrise in downtown Santo Domingo. 

I then spent the morning doing laundry and listening to NPR. The Airbnb had a washer and dryer, so I had packed piles of dirty laundry. It was a very normal weekend morning for me—it just happened to be in a wholly different place. 

JUNE 13, 2021 • PANAMA CITY, PANAMA

Toward the end of my time in the DR, I realized that I did not have a place to return to, so I started looking at where I could go next because I had had a really great week. I ended up flying directly to Panama, using the miles I got from my flight to the DR. I had an option: I could’ve flown through Miami on American Airlines—Oneworld Alliance airlines are what I normally fly—but it was fewer miles and direct to go on Copa Airlines. So, I just transferred a few miles over from my Chase Ultimate Rewards into my United MileagePlus account, and I think I ended up paying just $33 in taxes and fees. It rained nearly the entire trip.

JULY 9, 2021 • LOS ANGELES, USA

After five days in Panama, I flew back to Los Angeles and moved directly into a new sublet I found on Facebook. So far this year, I’ve traveled almost 50,000 miles. I’d like to earn one million points this year, and I actually think I may do it. Next up this year, I have trips planned to Alaska, El Salvador, Senegal, Portugal, Ghana, Chile, Colombia, Mexico, and I’m always lookingfor more. I don’t think I’ll make it to Antarctica and Australia (the two continents I haven’t visited this year), but I plan to hit both as part of my 2022 travels, which I’m already getting lined up. I really want to see some penguins.

THE FINE POINTS OF HENRI’S POINTS HACKING
Credit cards: Currently 14
Favorite card: Amex Gold (it gets 4x the points for restaurants and groceries)
Countries visited: 46
Countries since being vaxxed: 6
Flights since being vaxxed: 22
Favorite airline: Alaska Airlines for domestic travel, Qatar Airways for international
Most-visited P&M websites: Doctor of Credit, AwardHacker, Travel Codex, One Mile at a Time, Upgraded Points, View From the Wing, The Points Guy, Straight to the Points
Points and miles accumulated since getting vaxxed: 400,000
Points and miles used since getting vaxxed: 280,000

Amanda Arnold is a freelance writer and editor, and previously was a staff writer at The Cut. Follow her on Twitter.