Rappaport is doing a mileage run — a trip taken for the sole purpose of earning frequent flier miles, specifically the "butt in seat" kind required to keep elite status on airlines. (Read more: Have Elite Fliers Been Downgraded?)
Carriers award status based on the number of miles flown during a calendar year, so November and December are crucial months for travelers who are trying to reach their elite-qualifying points goals. They look for cheap fares with long routes to put as many miles into their accounts as possible. The strategy is so common that Flyertalk.com has a whole forum devoted to mileage runs and the future freebies they can ensure.
Rick Ingersoll, who writes the Frugal Travel Guy blog, says putting together the perfect mileage run is like a game.
"We're trying to beat the system," Ingersoll told TODAY's Janet Shamlian. "I have been to 65 different countries using these techniques."
Rappaport, 33, takes two or three such trips a year to maintain his Diamond Medallion status on Delta Air Lines and Executive Platinum status on American Airlines. He doesn't care about the destination, just how many miles he will get for the cost and how long the journey will take.
Ask him whether he regrets coming to a scenic place like Hawaii and not seeing any part of it, and he's quick to answer.
"Not in the slightest. I wish I could spend some time there but what it comes down to is the purpose of the trip is to get miles," Rappaport said.
"My wife has no problem calling me crazy. My mother shakes her head, my brother calls me crazy, most of my friends call me crazy, but they are intrigued by it because they know me and they know that I tend to take things to the extreme."
The Maui trip will re-qualify him for the top-tier status at American. To do the same thing on Delta, Rappaport recently put together another exhausting itinerary. He flew from Washington to Atlanta, then to New York, then to Istanbul, Turkey, where he spent the night and walked around the city for a few hours. He then hopped on a plane to Paris, then to Salt Lake City, then to Baltimore.
Rappaport's coach ticket was upgraded on the flights heading to Istanbul, but it was back to economy class on the way home. The trip required 27 hours in the air and left him sleep deprived and exhausted.
"It was a bit much," Rappaport conceded.
The airfare cost $665 and the Istanbul hotel set him back about $85, Rappaport said. He earned about 14,000 miles towards his status with Delta and about 35,000 frequent flier miles total when bonuses and promotions were taken into account — enough for a coach ticket from the U.S. to the Caribbean.
But Rappaport — who flies more than 100,000 miles a year for his job as a product manager for a software company — is happiest about getting to keep the extras that come with his top-tier status, like upgrades and free meals on flights. (Read more: Virgin America Woos Elite American, United Fliers)
"It's a lot of time up in the air so any little perk that you can get goes a long way," Rappaport said.
"(Also) I have more miles that I can then use to take my wife somewhere ... we really appreciate travel, we both want to see the world and I really don't want to fly to the other side of the world in coach."
The couple is flying first class to Thailand in January, to Poland in May and to Bali in July — all for pennies on the dollar because of Rappaport's frequent flier miles obsession.
Meanwhile, he's getting ready for what most people would consider the least romantic trip to Hawaii ever. It won't be so bad, Rappaport said, as all of his upgrades have cleared so he'll be flying first class the entire way.