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 was previously the CTO and a co-founder 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 it's 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.

Twenty-one 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 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. The airline didn't seem surprised the 21-hour trip had shown up as an option. In fact, they appeared to view this kind of itinerary 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 the 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.