Not even Conan O’Brien can resist the small-town charm of Stars Hollow! The comedian found himself unexpectedly drawn into the quaint, quirky world of Gilmore Girls recently when he and a few members of his team headed down to Havana, Cuba, to film the March 4 episode of his late-night TBS talk show.

The Conan host and his crew spent four days mingling with locals and soaking up the scenery in Cuba, where there’s currently an embargo that restricts trade and travel to and from the U.S. (President Obama has announced plans to ease those restrictions this year.) When they first arrived there from Miami, though, they lacked the necessary documentation to actually enter the country, and found themselves temporarily stranded at the airport.

“There’s no Internet, and phones don’t work. So we get off this little plane and we walk over this tarmac and we’re alone,” O’Brien told Us Weekly and other reporters after the trip, at a Feb. 25 lunch at New York City’s Trattoria Dell’Arte.

Eventually, they came upon a “very genial” man who asked them to hand over their visas — which they didn’t have. Instead, they gave him the only paper they did have, a form from the production company that was supposed to “take care of everything,” and he walked away.

“We’re like, we don’t know if he’s coming back!” the comedian recalled. “And if he’s not coming back, we have no phones, we’re in Cuba, we had this idea that we thought was going to be pretty cool, and we might be just completely f–ked.”

It was then that O’Brien spotted some familiar faces — those of Lauren Graham and Alexis Bledel, who played mother-daughter duo Lorelai and Rory Gilmore, respectively, on the WB series Gilmore Girls, which ran from 2000 to 2007.

“We’re standing outside, not knowing what to do, and we go into this very small, not impressive building where women and airport workers are sitting around and looking so bored because there’s nothing to do and there’s not a lot of traffic. And in the corner there’s an old television, and it’s showing Gilmore Girls in Spanish,” he explained.

“I had this [feeling] of comfort just for a second, so I wandered over to the TV, and I’m looking at Gilmore Girls, and it’s an episode where Rory has decided to leave Yale,” the Harvard alum continued. “Edward Herrmann is upset, and people are like, ‘She can’t leave Yale, it’s her dream!’ And she’s saying, ‘I’m going to leave Yale!’ And I’m getting lost in it for a second, and I’m looking at these Cuban people who could give a s–t about whether Rory leaves Yale or doesn’t leave Yale.”

Ultimately, O’Brien and his production team escaped airport limbo and made it into the city, where they immersed themselves in the local culture.

“I felt really strongly about it — I did not want it to be a smart, snarky American comedy take,” he shared of his vision for the hourlong episode. “I don’t want this to be political. A lot of my remotes are me as a fish out of water. The joke is usually on me, so I want to go sort of as a comedian who’s making fun of himself, and I want to make the Cuban people laugh and meet them.”

To that end, O’Brien tried his hand at rolling cigars, speaking Spanish, salsa dancing, and even playing “authentic Cuban music.”

“There’s a segment that I really love where I’m learning to sing with a real serious Cuban band, and…I’m not quite getting it,” he shared. “And then I burst through and start using eighth-grade Spanish to improvise this song, and the guys in the band are really laughing, and I’m saying things like, ‘The cat is in the sky, the dog has no milk,’ but I’m singing in full passion, and the band is cracking up…I wish I had been able to sing it better, but that’s usually how it goes.”

Conan’s trip to Cuba airs Wednesday, March 4, on TBS.