by | May 23, 2026
Editor’s Note: Florida Man, Rising
Editor in Chief Jamie Rich on reconnecting with an old friend and the memories made along the way
Florida Man gets a bad rap. Usually, the internet meme dominates headlines by wrestling alligators on the highway or robbing a Waffle House. But in the case of Bert Kreischer, who began his comedy career with a now-famous bit about burglarizing a train during a Florida State University study-abroad trip to Russia, the ultimate Florida Man—and our cover star—is busting out a trove of funny ventures and ascending to new heights of stardom.
The last time I spoke with Bert, in 2019, COVID wasn’t even a twinkle in our collective eye, but his career was already shining—with 1 million followers and a handful of cable TV shows and comedy specials. Fast-forward seven years, and “The Machine” is on his way to the top of the comedy food chain. With 3.5 million Instagram followers, he’s devouring audiences in his new Netflix sitcom, “Free Bert,” which just renewed for a second season, dominating the airwaves with his free-wheeling podcasts and manhandling fans on his “Permission to Party World Tour.”
Read Our Feature Story, Bert Kreischer: Ultimate Florida Man
Catching the stand-up comedian between shows meant flying to Los Angeles to meet him in all his shirtless glory (he performs bare-chested). When I arrived for our photo shoot at his studio—a cozy home in the LA suburbs where he records his “Bertcast” and “2 Bears, 1 Cave” podcasts—Bert had just flown in the night before. Wearing only shorts and de-puffing eye pads, the Tampa native didn’t take long to start dropping Florida lore, recounting the history of Ybor City cigar factories (he’s a stogie fanatic), and bantering with his wife, LeeAnn, about moving back to his home state (“It’s way too hot,” she says).
I first met Bert in 1996, when we were both students at FSU—him holding court by a bonfire behind the ATO house, me taking mental notes I didn’t know I’d one day use to write an editor’s note in my own magazine. Back then, Florida felt like a backdrop. Today, it’s a muse and the meaning behind toga-wrapping our cover model in the state flag. Which brings us here.
In this Summer Travel Issue, we explore the places and stories that make Florida more than a punchline—and Bert turns out to be a pretty good guide. In our cover story, the former travel-show host shares some of his favorite spots to visit across the state.
From there, we ramble on. We follow the pickleball boom, mapping out where to play, stay and compete—from luxe resorts to public courts. A night at Monster Jam leads us to the garage of the Pagliarulo family, Florida’s own monster truck dynasty. And along Florida’s coasts, we climb to the top of 10 of the state’s most storied (and haunted) lighthouses—holding on for dear life. Then we hop a plane to St. Martin, an often overlooked but contagiously vibrant Caribbean gem.
For the wanderers who love art, food and music, we have an itinerary of the senses—from a spaghetti al limone by James Beard nominee Bryce Bonsack to a centennial hit parade by artist Robert Rauschenberg and the latest vinyl spinning at Miami’s Sweat Records. Along the way, there’s grazing bison, hooting owls and rolling tarpon. And, of course, we can’t forget our lineup of hotel recs, table reservations and summer soirees, curated to inspire some spontaneous road trips.
Back in LA, before I left Bert’s studio, I pulled out a copy of the 1997 Rolling Stone article I had kept from the first time Flamingo featured him. When I asked him to sign it, he didn’t hesitate. “This is where it all started,” he said, scribbling his name on a grainy image of him partying in FSU’s Westcott Fountain. I couldn’t help but marvel at how far we both had come since the days of jumping in those hallowed waters. So, this summer, I invite you to chase the kind of stories you don’t simply read about, but completely jump into—you never know where they might take you.
FOR MORE NOTES FROM FLAMINGO EDITOR IN CHIEF JAMIE RICH, CLICK HERE.
About the Author
As an editor and journalist, Jamie has covered travel and culture around the world. Her work has appeared in national and international publications. She spent much of her professional life abroad and worked in newsrooms from The Moscow Times to The Times of London. She holds degrees from Florida State and Georgetown. She founded Flamingo in 2015.
