End of Summer Break: MAGA Flotilla

A Visual Recap - MAKE AMERICAN FESTIVE AGAIN.

PHOTOS BY DENISE BOVEE

As we gear up for our second MAGA flotilla, it feels like the perfect time to rewind and reflect on the spectacle in Jupiter, Florida, we were part of at the close of summer: a parade so bold, so over-the-top, it defied containment — an ocean of red, white, and blue devotion swelling on the water, flags snapping like applause for the Commander in Chief.

To truly grasp a MAGA boat parade, you have to be right in the thick of it. I’ve never seen a Trump-themed flotilla captured from such an intimate perspective—and in this case, perspective is everything. From the inside, it’s not just the flashy show of elite wealth the media paints it to be. It’s something more inspirational—the embodiment of American spirit: loud, proud, and utterly unbothered. It wasn’t just about the yachts; there were vessels of all sizes, including a guy waving a flag on the tip of his jet ski, all united in a patriotic display for “everyone’s favorite president.”

From the shore, it might appear as just another display of 1% excess—a parade of gleaming yachts and oversized egos. But up close, it was a mix of unlikely characters: dinghies brushing up against mega yachts, paddle boarders somehow keeping pace with cigar-toting millionaires, all exchanging high-fives as they passed by. You really can’t compare this level of adoration to anything else in modern times. I wonder if even Trump’s harshest critics wouldn’t find a hint of intrigue in it.

A lot unfolded over that August afternoon. At one point, I left the family behind to yacht-hop and mingle with the MAGA faithful. When Drea Vernazza’s massive yacht cruised by, it looked like a scene straight out of a Hype Williams music video—champagne popping, flags waving, music blasting. Exactly what Leon Kraus’ TikTok dreams are made of. And yet, somehow, it all made perfect sense. Of course, this is what summer break during an election year would look like.

When I returned two hours later, Hayes had been unofficially adopted by Caroline Wren and the Bannon crew, looking like he might start fifth grade with an indictment under his belt. Arlo, meanwhile, was sprawled out on a leather ottoman next to a beautiful blonde who had commandeered the sound system. “I know who I’m voting for,” he smirked, clearly swept away by the allure of the young, hot women that MAGA tends to attract.

Leon was fast asleep on the front, Mike had made second and third rounds at the breakfast buffet, Hayes had fully integrated with the J-Sixers, while Arlo somehow managed to land a handful of Miami connections, get booked on a podcast, add a stock exchange app to his phone, and get his hands on a cigar (which I promptly confiscated). I blinked, wondering if I had wandered into some alternate reality.

One yacht felt like a scene straight out of a Leonardo DiCaprio film—more sunscreen, less subtlety. As I walked in, I couldn’t help but think, "What in The Wolf of Wall Street is going on here?" Boomer men in sleeveless polos, cigars dangling from their lips like accessories to their blustering egos, Fox News murmuring in the background, all while a sparkling ocean nursed their hangovers. They sipped straight liquor from plastic cups, and when their cigars burned down, they half-heartedly looked for an ashtray before tossing them into the water, their eyes glued to their phones as they checked for the latest bump in stocks.

I didn’t even realize I had landed on ‘MAGA’ Meg Weinberger’s boat until I was alerted. Congressman Brian Mast was in charge of the sendoff. He took the speaker shirtless. Mast, a decorated U.S. Army veteran, lost both of his legs while serving in Afghanistan in 2010. As an Explosive Ordnance Disposal technician, Mast was working to clear a path for fellow soldiers when he stepped on an improvised explosive device, resulting in the loss of his legs and a finger. Despite the life-altering injuries, Mast's resilience and determination led him to pursue public service, becoming an advocate for veterans' issues and national security in the U.S. Congress. On the boat that day, he was a fired-up MAGA hype man giving the parade the green light. On the same boat, Laura Loomer was aboard, demure among the crowd in a red bikini.

At one point, we swung by Don Jr. and Kimberly’s waterfront mansion to pick up Kimberly. Their sleek, white compound gleamed by the shoreline, their boat docked out front. They waved from the dock like they were part of a monument to the day’s exuberance. A small boat even offered them a letter and a CD filled with songs written for Don’s father.

I couldn’t help but laugh at the surreal nature of it all. After an eight-year journey, this is where life had taken me. One minute, I’m marching in D.C. with pink pussy hats, chanting an array of anti-Trump slogans. The next, I’m yacht-hopping with MAGA’s most decorated and devout, singing along to Kid Rock’s Cowboy—lyrics I didn’t even realize I now had etched in memory.

If someone had told me eight years ago that I'd be here, I’d have assumed they were writing the plot for a satirical reboot of The Twilight Zone. But here we are, living it, and somehow it’s not a nightmare—it’s summer break at its finest.

This campaign stop—disguised as a vacation—is one that the Kraus boys (and my adopted fifth son, Finn) won’t soon forget. In a world where everything feels upside down, this MAGA yacht parade might just be the most perfectly chaotic expression of America itself: an odd, bloated, flag-waving, champagne-popping spectacle where every dinghy and cigar finds its place in the water. A flashy brand of patriotism where every boat and status is welcome.

---

Thank you Lynne Patton for the invite and Drea Vernazza for welcoming my family on your yacht.