How I Travel: Questlove Is Finally Learning How to Vacation

Ahmir Thompson, best known as Questlove, has not really stopped producing content once during his fifty years. While most know him as the drummer of the Roots, which has been the house band of The Tonight Show since 2014, he’s also a radio host, composer, Broadway producer, author of four books, actor, and now, a filmmaker: he makes his directorial debut this month with Summer of Soul (…Or, When the Revolution Could Not Be Televised). The documentary, in theaters and on Hulu now, shares the story of the Harlem Cultural Festival, a nearly forgotten concert series the same summer as Woodstock that featured performers like Stevie Wonder, Gladys Knight, and Nina Simone.

In case it wasn’t clear, Questlove isn’t really a kick-back-with-a-tiki-drink kind of guy when it comes to travel. “I’m super notorious,” he says. “My reputation is known for being anti-vacation. The pandemic slowed that down, and made me realize the importance of resting.” He shared his other inspiration for more leisure time, as well as his favorite cities and why private planes are overrated, with Condé Nast Traveler.

His catalyst for trying to become a vacation person:

In the past five years, I’ve struck up a friendship with a gentleman named Shep Gordon. He had a documentary made about his life, directed by Mike Myers, called Supermensch. And when I saw Supermensch, I went on social media and just stalked him, like, “If anyone knows who Shep Gordon is, contact me.” Weird enough, Apollonia was like, “That’s my BFF.” So Shep, he invented the rockstar manager rule book, like everyone from Alice Cooper to Anne Murray to Teddy Pendergrass, Rick James. He’s had them all. Like me, he was a workaholic, and then one day he just walked from it all. He’s just like, “I’m letting everything go. I’m going to make relaxation my priority.” He basically opened up a utopian getaway for fellow workaholics. All you have to do is call him up and say, “Shep, I need a break.” Once a year, for the last five years, I go to Maui just to do nothing. It’s his house, and it’s really simple, a beautiful, sprawling estate. But he has the world’s best grass. There’s nothing like walking on his grass with your bare feet. That’s one of my top five feelings in the world, is just to sit and let hours go by. And that’s the thing, I go there specifically to do nothing. Sleep, sit, and do nothing. Wake up and go back to sleep. Just to unwind.

His love affair with JetBlue:

People think I’m joking, but I’m dead serious—JetBlue Mint, to me, is even better than private planes. Private planes aren’t fun at all. The only good thing about private planes is the bragging that you get to do in that 20 second walk up to the plane. Once you’re in it, there’s no space. I’m in 11-man groups, so you’re crunched in there. If you’re the kind of person that gets off on that one Instagram story that makes it look like your life is that fabulous, more power to you. But for starters, [JetBlue has] the right balance of the movies I like to watch. Right now, their whole summer is dedicated to Hitchcock. I usually catch up on the black and white films or musicals or thrillers that were done between the ’50s and ’60s that I always say I’m going to watch and never do. I’ll say that yes, I often do sometimes just go to sleep, but most of the time, if I’m on a plane, chances are I’m doing a DJ gig, so I’ll practice what my plan is going to be.

His ranking of the world’s best cities:

My all-time top five cities, places I would like to spend the last part of my life if I didn’t have to work… My all-time favorite city in the world is Portland, Oregon, because that’s the best place for record shopping. I’ll say maybe 60 percent of my entire record collection comes from Portland. Not to mention food truck culture is very big there. There are movie theaters; I’m a big old-timey movie theater expert. Second place is Austin, which is kind of a twin to Portland. Same thing: food culture, food truck culture. My third place is Tokyo. Again, I base all my spots on accessibility to rare records, rare artifacts, rare pop culture items. Montreux, Switzerland, is probably my favorite European city of all time. Taking the train from Paris to Montreux in the afternoon, there’s nothing like it in life. Even when we do the Montreux Jazz Festival, I make sure that I fly to Paris so that I can take the train up there. And fifth, I’d go back to Maui.

A destination he thinks is underrated:

What place really shocked me? Charleston. I’m often curious about these one-off, hippie college towns in places that aren’t necessarily hippie. A blue city that’s inside of a red state, that sort of thing. Charleston, the town is sort of built in the image of New Orleans. It’s almost the exact twin of New Orleans, and it’s really chill and amazing. We did two shows there and I put it on my list like, “Okay. This is a really interesting town. I like it.”

What he recommends to visitors to his hometown:

Any of my friends that go to Philly, my job is to stop them eating tourist cheesesteaks. It’s the equivalent of like going to 42nd Street, going to Times Square, when real New Yorkers—no one hangs in Midtown, Times Square. That’s where the tourists go. I’m that way with my cheesesteak recommendations. Whenever anyone goes to Philadelphia, I have to become their Zagat guide on where to eat. Stop them from tourist cheesesteaks!

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