“Throwback Trips” Use Adult Money To Accomplish Childhood Dreams

I’m nostalgic to a fault. While I’m technically a Gen Z cusp, having an older sister makes me relate to all things millennial. Sure, I love a TikTok trend, but I know ball — as tweens, while she was wearing Victoria Secret’s Love Spell, I was wearing cucumber melon body spray. Last year, I tracked down two vintage Dolce & Gabbana bags because they were the same style my sister and I had knockoffs of when we were in elementary school. I’d be lying if I said I haven’t searched for Ed Hardy on eBay recently. Point blank: Any time or money spent tending to a childhood interest is well spent to me.

So when I got the opportunity to bring her along to a T-Pain concert, the same artist I remember blasting from her wall-mounted CD player as a kid, it was a no-brainer.

I’m not the only one down to travel for a sentimental concert. Today, 2000s nostalgia has officially transcended past capris and ballet flats — it’s shaping vacations, too. If tickets for your childhood fave’s show in your hometown sold out in minutes (like many of Hilary Duff’s did), it makes sense to track down tickets elsewhere. If you’re a truly committed fan, a full tank of gas or a boarding pass is a small investment toward making your childhood dreams come true. Enter: the “Throwback Trip.”

What you do with your PTO is totally your prerogative — why not spend it singing songs from your old playlists?

Throwback Trips may not be as luxurious as a European vacation based around the Eras tour or as convenient as the concert stop in your home city. To see their nostalgic faves, people are willing to fly to Indianapolis, like user @bethanylearmont, who did exactly that to see Hilary Duff on tour. Similarly, during No Doubt’s residency at the Sphere, elder millennials have had no problem booking airfare to see their faves. Take Sarah Marcotte, who says she spent an estimated $1,550 on her trip from Arizona to Las Vegas (“But honestly for a No Doubt reunion show I would have traveled across the US”). Another TikTok user vlogged her road trip to see Shakira this month.

A few years ago, people on TikTok started calling out all of the ways they still feel like a “teenager in their 20s”: loving teen romance shows, reading fan fiction, and buying things they wanted but couldn’t afford as kids. With plenty of artists who dominated the 2000s going on tour this year, it’s a perfect time for millennials to take a Throwback Trip. And while missing a day of second grade for a concert felt like a borderline blasphemous thing to ask your parents, as an adult, what you do with your PTO is totally your prerogative — why not spend it singing songs from your old playlists?

I went on my own Throwback Trip last month when Chase Sapphire Reserve invited me to Montauk for a T-Pain concert at their Delilah pop-up, which featured roaring-’20s-themed decor, showgirls, and a moody aesthetic exported from the original dinner-and-drinks hot spot from Los Angeles. For the second consecutive summer, Chase Sapphire Reserve gave card members exclusive access to a two-weekend experience that included a prix fixe dinner, a vintage photo booth, exclusive merch, a Vivrelle claw machine, and a concert lineup featuring other #TBT stars like Mike Posner and Nicole Scherzinger. My sister and I took a three-hour road trip from Brooklyn to the Hamptons. Even though I’m not the biggest fan of driving, knowing what the pop-up would have in store was well worth it.

The entire weekend had the vibe of a slumber party with a hint of girls’-night-out energy. My sister and I laid in our robes for a little too long before getting ready. I did my makeup sitting crisscrossed applesauce on the floor in front of a full-length mirror, which is exactly how I used to get ready for school in my childhood bedroom — except this time, we pregamed with dirty martinis from room service. We helped each other choose our outfits and sang along to T-Pain, somehow still remembering all the words to the songs we used to sync to our iPods.

I’m a quintessential little sister through and through. I live life by the seat of my pants, my sister prefers a set plan; I’ll fall asleep at 3 a.m. without charging my phone, my sister prefers a solid eight hours of sleep. Being together brought out that contrast even more. And while I (29) think mid-30s is still sprightly, she reminded me several times that she didn’t feel young enough to keep up. Thank goodness for those energy drinks we had before getting ready.

When we arrived at Delilah on Saturday night for the concert, we grabbed spicy margs and made our way to a table with a clear view of the stage. We mingled with other guests, making small talk about how we all made it out east (some took the three-plus-hour train ride for their own Throwback Trip), and made guesses about what song he might open with. (My bet: “Can’t Believe It.”) When the first chords of “I’m Sprung” began, nearly everyone was out of their seats dancing and singing along.

The set was a little less than an hour long, and my sister and I both joked about how at this age, that’s kind of the ideal length of a concert. We ate hors d’oeuvres and enjoyed bottle service with our tablemates, and while other guests kept their nights going past midnight, we were already calling our Lyft back to the hotel by the time the rapper bade farewell to the audience.

Seeing an artist from our tween years at a place with fancy cocktails and a raw bar reminded us that regardless of how we might regress when we’re together, we’ve grown a lot. I’ve made a life and career for myself in New York City. She’s settled down in the suburbs and made my favorite human alive, my 2-year-old nephew. Still, our music taste hasn’t budged.

That’s the magic of Throwback Trips: Treating your inner child helps you appreciate just how far you’ve come. Some things will never change — like knowing every word to “Buy U a Drank” by heart. This time, though, we sang along with drinks (dranks?) in hand.