How I Travel: Dan Levy

Dan Levy: Cracking Jokes, Collecting Miles

Your chances of sitting next to Dan Levy on an airplane are relatively high—considering the wandering comedian gathers miles obsessively. If that happened you’d soon consider yourself very lucky; Levy is funny as hell and a genuinely friendly guy.

Over the past decade, his humor has been featured on “Comedy Central’s Premium Blend,” “Chelsea Lately,” “The Late Late Show,” “College Humor’s I Have to Go In a Minute Show” and on his own special: “Comedy Central Presents: Dan Levy.” 

Dan didn’t get his coveted American Airlines Platinum Miles Card without forming a few opinions on how to travel and this week he was kind enough to share them with BootsNAll.

My first travel memory was me, my mom and my dad going to South Florida to visit my grandparents.

I remember being really excited to go to Florida and then really scared because everyone was so old.

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I am very minimal when I travel.

I never check luggage. I refuse to check luggage. I look down at people who check luggage. When I get on the plane I have a backpack with my laptop and a carry-on—that’s it.

If you’re going to check luggage…

you basically should just get back in your car, go home and not fly anywhere.

I never check luggage. I refuse to check luggage. I look down at people who check luggage.

My dad got me addicted to collecting miles with American Airlines.

I would say I’m addicted to American Airlines, similar to George Clooney’s character in Up in the Air. I only fly American. I’m executive platinum status, which I’m very excited about. I don’t brag about anything…except for being Executive Platinum—‘cause that shit is awesome!

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Join the miles club of whatever airline you fly.

The Admiral’s Club changes everything. There’s coffee, internet, food, good people. It changes the whole experience.

I have flown over a million miles on American.

If you’re traveling in one country you have to specialize with one airline…I hear United has some great perks too but I’m committed to American for life at this point.

I got upgraded once and sat next to the president of American Eagle.

Afterward I started e-mailing him back and forth for awhile and until I realized that I had nothing in common with him…so we lost touch.

Right now I pretty much only travel for work.

Basically the way I look at vacations is I see where American Airlines flies and then I go from there.

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I ate frog legs this summer, which was weird.

That was in Turkey.

The first thing I do when I land is get to my hotel and completely unpack.

Even if I’m only going to be someplace for twelve hours, I completely unpack everything. I’m not autistic; I just like to be very unpacked.

I just joined the Hilton Honors.

I’m getting into the hotel points—that’s the next step.

Even if I’m only going to be someplace for twelve hours, I completely unpack everything.

I never leave behind…

my laptop, my noise-canceling headphones and my sleep mask.

When you fly: don’t wear sweatpants.

Wearing sweatpants on a plane is like wearing a fanny-pack walking around Paris. It’s pretty much the same thing.

I was on a plane once that lost all cabin pressure.

We had to make an emergency landing in Buffalo. My nose started bleeding because there was no air-pressure…and then we realized that the only thing worse than crashing and dying was landing in Buffalo.

The one time I checked a bag was on a vacation to Aruba.

And they lost my luggage.

I’d love to go back to the Amalfi Coast.

I’d also love to go back to the Greek Islands and I really want to go to Japan and Australia.

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The best restaurant I’ve ever been to on the road was Alinea in Chicago.

It was like 18 courses and absolutely unreal.

I like Hollywood.

A lot of people complain about LA. I’m from Connecticut, but I really enjoy Southern California.

I love trains.

The train ride from New York City to Boston is one of the most relaxing train rides ever. I took some great train rides in Italy, too. I went from Italy to Germany, which was perfect—because you’re bringing out wine and all of that. It’s funny, because I fly so much but I don’t necessarily love flying. I hate rental cars—they always screw you with rental cars.

I listen to a lot of “sleepy time music” to help me sleep on planes.

Like eight-minute long tracks of stars smiling and waves crashing.

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My favorite place I ever performed was Hawaii.

I just loved the lifestyle, the relaxation, and how beautiful and carefree everyone was. The weather was unbelievable. It’s easy to forget you’re in America over there until you see some fat guy in a Mississippi t-shirt, then you’re like: “Oh, yeah, still in America.”

One time I sat on a plane next to Britney Spears’ mom.

That was hilarious. We talked about Britney for two and a half hours.

I love travel because I really like keeping my life fresh.

And when I’m just about to get bored back home, I’m on the road and everything feels new and exciting again.

Catch up with Dan online at and be sure to follow him on Twitter.

“How I Travel” is a BootsnAll series publishing every Friday in an effort to look at the unique and diverse travel habits of some of the world’s most well known and proficient road warriors.

all photographs provided by Dan Levy and may not be used without permission

Filed under: featured, How I Travel