This Southwest Passenger Found a 21-Hour Itinerary With 5 Stops From BOS to SFO. Here's Why He Took It Anyway

Software developer Rafael Mendiola says he was doing a research project for work when he found an insane Southwest Airlines itinerary online: five stops, with an early morning departure out of Boston and a very late arrival 21 hours later in San Francisco. 

It was utterly crazy–especially considering you could do the same trip nonstop in under seven hours (and for less money).

“Wouldn’t it be funny if somebody actually took that flight?” joked Mendiola, who works for business travel management system Lola. “And I immediately ‘got volunteered’ to do it.”

From Kayak to Lola

I talked recently with Mendiola and his boss, Paul English, who started Lola and who was previously the CTO and a cofounder at Kayak (and who, last time I checked in with him, was driving an Uber in Boston).

The idea for the research and Mendiola’s crazy trip had been to study the customer experience at more established services, like Concur. English contends they can swamp business users with irrelevant options, focusing on price above all else.

“We think at Lola that important to show every possible option, but we don’t steer you toward taking the cheapest option. From Boston to San Francisco for example there are so many non-stops. … We thought it was ludicrous that Concur shows these itineraries, with no concern for comfort–just cost,” English said.

21 hours on Southwest

As for having Mendiola actually take the 21-hour trip, it sounded to me like a marketing stunt–one that worked, I acknowledge, since I’m writing this article).

Although English insisted, “it wasn’t really a marketing thing,” so let’s call it research, or a joke–or even just a way to haze a (perfectly willing) software engineer. Regardless, here’s what it was like actually to book this insane, 21-hour itinerary, and then actually take the trip on purpose last October.

  • Mendiola and his girlfriend left home at about 4 a.m. for Logan Airport, where they took Southwest flight 3219 to Denver, departing at 6:35 a.m.
  • In Denver, they had a one-hour layover before taking the exact same plane, still flight 3219, to San Antonio.
  • After a 2 hour and 15 minute layover in San Antonio, they flew to New Orleans on flight 1719.
  • Thirty minutes later, they took the same plane (still flight 1719) to Phoenix.
  • Another 40 minutes on the ground, and they took the same plane yet another time (once again, flight 1719) to Las Vegas.
  • Finally, after another 35 minutes on the ground, they boarded flight 1719 one last time, for San Francisco, arriving at 11:25 p.m. local time, 21 hours after their departure.

“We got to know the flight attendants very well. They were very nice,” Mendiola said. “We told one of them what we were doing, and she said, ‘Oh bless your heart.'”

A feature, not a bug

Upon arrival in San Francisco, Mendiola said they went straight to sleep. The next day he and his girlfriend got massages as a reward for their rough trip.

Hopefully he got an even bigger reward at Lola when he returned. The Boston-based company raised a Series B round last year and has 50 employees.

By the way, I asked Southwest Airlines about Mendiola’s itinerary. They airline didn’t seem surprised that the 21-hour trip had had shown up as an option. In fact, they appeared to view this kind of intinerary as a feature, not a bug.

“When we switched over to our new reservation system last year, we were able to institute something we refer to as ‘Dynamic Connections,'” spokesperson Dan Landson told me in an email. “This allows customers to see all travel options between the cities they are traveling between. It also gives them the ultimate flexibility to choose which routing, time, and price point that meets their travel needs.”

So if you ever choose to spend 21 hours flying when five and a half would do it, you know where to find your flight.

'Hero' United Airlines Passenger: I Almost Didn't Take That Flight

You might have seen the name Chase Irwin. He’s a Nashville restaurant manager who became a little bit Internet famous and was hailed as a hero recently, after he aggressively called out a fellow passenger on United Airlines for “body shaming” a third passenger in a text message.

The whole episode never would have happened, Irwin told me, but for a ridiculously big change fee on another airline.

He’d had been in Oklahoma City for a graduation, and his ride to the airport got him there 12 hours before his scheduled departure. Switching to an earlier flight on Delta would have cost him $900, he said. So he scrapped that and bought a ticket on United Airlines instead.

That’s what landed him in seat 15C of a United flight to Chicago, for the first leg of his trip, which had a 30 minute delay. As they sat on the tarmac, he said had a clear view of the cell phone the male passenger diagonally ahead of him, in 14B, was texting on. 

“The guy had his phone out far from his face. The font size was really big. And I saw the words, ‘sitting next to a smelly fatty,'” Irwin said. 

Then, Irwin said, he saw that the woman in 14A was crying, and looked like she was trying hard to push against the window away from the man. Irwin leaned forward and read the rest of the man’s message. 

He grew incensed. Over the next few minutes he talked with two flight attendants, and worked out a plan with them to convince the man to change seats with Irwin, so that the woman wouldn’t have to sit next to him.

Irwin, 34, who is about six feet tall and 200 pounds, told me he stood up and grabbed the shoulder of the passenger who’d been texting, who was about 5-foot-6 and “160 or 170,” and seemed to be in his 50s or 60s.

“You’re a heartless person,” Irwin remembered saying, and ordered him to switch seats. “I wasn’t quiet. I wanted people around him to see he was a jackass.”

The other passenger actually said “thank you,” perhaps not understanding the context, and Irwin said he sat next to the woman and tried to take her mind off the offensive message (which she had in fact read) for the rest of the flight. 

Based on Irwin’s account alone, it might be a bit hard to know what to make of this whole thing. The unidentified texter was impolite, but he did seem to be sending a private message. 

Meantime, Irwin used his size to act aggressively against another passenger on an airliner, with the apparent assent of the flight crew. 

However, the story only came to light because the woman passenger, Savannah Phillips, posted about it publicly afterward on Facebook—-as a way to try to find Irwin and thank him for what he’d done. That post went viral (more than 1,500 shares  so far), and commenters almost unanimously praised Irwin for his actions.

“The flight attendant kept trying to give him free drinks and told him that he was her hero,” Phillips wrote. “He wasn’t her hero–he was mine. …  I told him that he was a blessing sent to me and how thankful I was that he was there.”

By the time his connecting flight landed in Nashville, Irwin, who is general manager of a bar there called Dierks Whiskey Row, said his company’s corporate office in Arizona had seen her post and had contacted him. He and Phillips reconnected within hours.  

United Airlines told Newsweek, which reported on the whole incident: “We appreciate the efforts of the customer and would like to hear from Ms. Phillips to understand what occurred.”