Tori Simokov, 33, and Dylan McDougle, 34, built their relationship on a shared sense of curiosity, creativity, and a lot of flying.
“I was actually terrified of flying when we met,” said Simokov, a consultant and author of Window Seat, a Substack newsletter. “But I flew every month to see Dylan. Over time, that fear transformed into fascination.”
The Brooklyn-based couple first met in July 2015 in Columbus, Ohio, where Simokov was living at the time. McDougle, who was touring internationally with a band, was in town for work. They hit it off at a concert, began dating long-distance, and for two years, their love story was written in airline miles and airport terminals.
That initial passion for aviation has become a cornerstone of their relationship. “Now we go plane spotting, visit aviation museums, and plan our lives around travel,” Simokov said.
The pair were married in June 2023. As they considered honeymoon spots, Japan quickly became a top choice. McDougle had a deep admiration for the country’s listening bars, intimate spaces devoted to high-quality sound experiences (the couple actually got engaged at a listening bar in Brooklyn). For Simokov, lifelong obsessions with Nintendo and Pokémon made Japan feel like the ideal spot, too.
“It just felt right to celebrate our marriage somewhere that reflects so much of who we are,” said Simokov. Once the destination was set, their goal was to book the trip entirely on points. This wasn’t your average honeymoon booking—it was a full-on masterclass in leveraging points. Here’s how they did it.
How They Booked The Flights
Tori and Dylan in their ANA Business Class seats.
Tori Simokov and Dylan McDougle
The Flights by the Numbers
The destination: Tokyo Total flight cost: $18,038 round tripPoints breakdown: 170,000 ANA Mileage Club miles for roundtrip business class on ANA between New York and Tokyo (transferred from American Express)The total spent: $0
Like any points aficionado knows, having a backup plan is key. Simokov and McDougle first locked in refundable Delta Premium Select tickets to Japan using SkyMiles, just in case nothing better came along. But what they really wanted was a pair of seats in ANA’s coveted business class product, The Room, which flies nonstop between New York and Tokyo Haneda.
“We were tracking ANA availability obsessively,” said Simokov. “Seats would open, then vanish in seconds.” (Tip: To check award availability for this airline, log into an ANA Mileage Club account, navigate to the Flight Awards section, and select “Award Reservation.”)
Knowing ANA only releases a handful of award seats each year, the couple made a risky move: They preemptively transferred American Express Membership Rewards points to ANA’s program without confirmed availability. Why is this risky? Because once credit card points are transferred to a travel partner, they cannot be transferred back.
Thankfully, two seats soon opened up, and Simokov and McDougle pounced. The only hitch? At the time, ANA only allowed for round-trip redemptions, meaning the couple could not book one-way flights using points (that’s now no longer the case). Since their preferred return date wasn’t available, they booked a return two days later than they wanted—and hoped for the best.
“We were in Japan, on our honeymoon, checking ANA’s website every day,” Simokov recalled. Miraculously, days before their desired departure, an ideal return flight opened up.
How They Booked the Hotels
Tori taking in the view’s from the Park Hyatt Kyoto.
Tori Simokov and Dylan McDougle
The Hotels by the Numbers
The Hotels by the Numbers
The destination: Tokyo and KyotoTotal hotel cost: $6,960 (for 9 nights)Points breakdown: 175,000 World of Hyatt points for stays at Park Hyatt Kyoto, Park Hyatt Tokyo, and Hyatt Regency Kyoto + 152,000 American Express points for a stay at Conrad TokyoThe total spent: $0
Originally, the couple’s itinerary included Tokyo, Osaka, and Kyoto. But once they landed in Tokyo, Simokov and McDougie completely fell in love with the city.
They wanted more time there after their initial stay at the Conrad Tokyo, which was booked through the Amex Travel portal. The couple decided to make a spur-of-the-moment decision to skip Osaka altogether.
That change threw a wrench into their hotel plans, however. They turned to Hyatt—their go-to loyalty program—to see what was available at the last minute. As luck would have it, the Park Hyatts in both Tokyo and Osaka had open rooms and incredible redemption values.
What the Experiences Were Like
The first business-class flight with ANA from New York set the tone for the entire honeymoon.
“The service was next-level,” said Simokov. “The crew surprised us with a personalized dessert when they heard it was our honeymoon. We even had enough room to curl up and watch a movie side by side—on a plane!”
While the couple stayed at several properties across Japan, two stood out: Park Hyatt Tokyo and Park Hyatt Kyoto. Ironically, neither hotel was part of the original itinerary. After falling in love with Tokyo, they decided to skip Osaka and extend their time in the capital—forcing a last-minute pivot on accommodations.
“We checked Hyatt’s site and couldn’t believe our luck. Both Park Hyatts had availability and great redemption rates,” Simokov said. Those spontaneous changes turned into their most luxurious hotel stays.
At Park Hyatt Tokyo, they scored a front-row seat to the iconic New York Bar, famously featured in Lost in Translation. “We were seated next to the jazz band with an unobstructed view of Tokyo. Then the band started playing my favorite jazz song,” Simokov said. “It felt cinematic.”
At the end of the trip, Simokov was feeling “deflated” about leaving Japan and going back to reality. However, that quickly changed. When she and McDougle arrived at the gate for their flight home, they realized the flight happened to be operated by one of ANA’s Pokémon-themed aircrafts; flying on one had been a dream of Simokov’s for years. “I immediately burst into tears,” she said.
The couple boarded to the sound of Pokémon gameplay music, met Captain Eevee in the galley, and were showered with thoughtful touches from the crew throughout the flight.
“I didn’t sleep a wink,” Simokov said. “It was one of the most special experiences of my life, and the perfect way to end our time in Japan.”
Points and Miles Tips
Simokov and McDougle credit much of their travel success to staying flexible throughout the planning process. Being open to shifting dates, routes, or even destinations unlocked far better deals than sticking to a set itinerary. They recommend making fully refundable backup bookings, which provide peace of mind while continuing to monitor for better redemptions or last-minute changes.
Finally, the power of leveraging business credit cards and checking account bonuses ahead of time allowed them to earn enough points for their honeymoon. For them, travel hacking isn’t necessarily about gaming the system—it’s about being intentional, patient, and prepared.
AloJapan.com