Simon Murray goes all-in on a poker run aboard the Midnight Express 60 — the builder’s biggest, baddest boat to date.

It’s hard to measure excess in Miami. Where to begin when even the ocean crashing intoxicatingly close to urban sprawl has a touch of the extravagant in every wave? In this sun-drenched climate, a fuel-efficient sedan feels all wrong. No, only exotic Italian sports cars will do. The American Dream as we know it might be contracting, but American Dream Miami, when it opens, will be the largest shopping mall in America. It’s pervasive. Follow the rumblings of dirt bikes to the graffiti-stained, bohemian glitz of Wynwood or the tapping of stilettos to the swanky clubs of South Beach and you’ll experience the same thing. Overindulgence isn’t an insult or a turnoff here, it’s a state of mind.

On a Thursday morning in February, no one in Miami seems to care that a coterie of powerboats numbering over 50 strong has set out from North Miami heading south; an armada of Tommy Bahamas on the warpath, sun dancing off stainless. As they snake in unison under the ICW’s low-lying bridges, traffic doesn’t stop. As they jockey, playfully, to be first in the procession, no one pulls over to the side of the road to whip out a phone. A helicopter circles loudly overhead—whup, whup, whup—the sole paparazzo, but even they are paid to be here by the Florida Powerboat Club (FPC), the organizing body of the 24th Annual Miami Boat Show Poker Run. The event was originally intended as a post-show manufacturers’ rally. Now it’s mostly just an excuse to grab some friends and get the hell out of dodge.

The first rule of poker runs is: You talk about poker runs. You tell your friends, your coworkers and depending on your relationship, your spouse. Each one is pure high-octane wish fulfillment for a certain demographic; fast, offshore power cats the boat du jour. It’s Miami Vice and Playboy and Margaritaville all rolled into one. Babe brigades in matching bikinis flaunting it because they got it. Entrants running fast and low over the waves, going point to point collecting cards. With the best poker hand winning—what exactly? During the entire trip to Key Largo, the final stop on our cruise, I never find out. It doesn’t matter. I’m too busy aboard hull number one of Team Midnight’s excessively large, 60-foot super console fulfilling the prime directive: using a fast boat the way its designer envisioned.

I know this because the designer is at the helm. Eric Glaser is co-owner of Midnight Express, and he’s brought with him some friends. Helping navigate is Brian Wilson, a software engineer from Miami Beach, Dustin Goldstein, a banker from Chicago, and Christopher and Gina Olsen, a couple from Ft. Lauderdale. This crew has a lot of experience on the water, with the Olsens alone estimating they have at least 20 poker runs under their belts.

After stopping to receive the first card in a sealed white envelope, Team Midnight leads the formation in a long drawn-out parabola, a playful dolphin riding our wake. But the offshore cats aren’t far behind, and soon they’re flanking us like a high-speed security detail. Before we disembark from his newly purchased waterfront property, Glaser tells me he’s looking to practice some rare restraint with the 60. “I’m not trying to go as fast as some of these guys,” he says. “We’ll stay around sixty, sixty-five [mph] for most of it.”

There aren’t too many situations where 50 knots—or a Midnight Express with four, 627-hp Seven Marine outboards—is considered slow. In fact, Glaser and his brother, Harris, have made a living building semi-custom, high-performance center consoles for an international clientele. (“I can always tell how good the company is doing by how many new cars are in Eric’s driveway,” says Wilson, who is only partially kidding.) And yet, in contrast, the offshore powerboats—Cigarettes, Donzis and their ilk—can easily exceed 100 mph.

A 46-foot Skater with a billowing American flag paint job sharks up alongside us. It’s single file under the North Bay Causeway, but patience and a Boy-Scout-like adherence to the rules doesn’t exactly fit with the whole offshore-racing mystique. As we clear the bridge, on our port side, a Wright Performance 360 with two jet-black 400-hp Mercury Racing outboards slinks under the pilings. She clears the gap by feet, if not inches, and takes off in search of blue water with the other cats in hot pursuit.

But hold on, because this isn’t a race. At least, that’s what I’m reminded every time I slip up and call it one. Stu Jones, founder of the FPC and one of the godfathers of the sport, tells me his club members don’t even utter the r-word: If they did, their insurance companies would drop them for engaging in provocatively reckless behavior. Instead, the focus is on showmanship, “because you’re not winning anything for the biggest fish, and you’re not getting a prize for having the fastest boat,” says Jones. “In our sport, it’s more about putting on a show and having a good time.”

At the end of the four-day-extravaganza, the FPC will give out two dozen awards. One includes “best center console,” a prize that would’ve been laughable in the sport’s heyday, beginning in the late ᾽80s. Back then, the only center consoles on the market were devoted entirely to fishing and had as much sex appeal as a Ford Pinto. But as the Midnight Express 60 is proof of, that’s all changed. I count at least six center consoles in the mix, including a couple Grady-Whites and the 59 Tirranna, Cigarette’s own category-breaking super console. And it’s not just Miami that brings these center console owners and manufacturers out in droves. Countrywide, their attendance, if not speed, is starting to rival the offshore cats.

Idling into Grove Harbour Marina at Coconut Grove, we pick up our second card and two more crewmembers: Stu Jones and Marissa Everhart, who stands out in a slinky bikini. Everhart, as the logo on her bikini asserts, is one of the “FPC Girls.” Our crew crowds around the console’s expansive bench seating or lounges on the aft sofas in the cockpit. Immediately, it becomes apparent why owners would gravitate to a fast boat with more versatility and utility than the traditional, single-purpose speed machines. It still feels like we could fit a dozen more as we clear out for Key Largo.

While underway, Everhart and Gina bond over a fondness for tattoos. “You’ve got one too?” asks Gina, after Everhart, a realtor by day, mentions something about having a Playboy bunny tattoo somewhere on her person. “The younger generation doesn’t understand; it was a big thing to get one back in the day.”

What doesn’t come up in conversation: Everhart has a Playboy bunny tattoo because she is a working Playboy model. In the world of poker runs, anything is possible, reality is a lie, and nothing, I mean nothing, is too good to be true.

“Life is not always a matter of holding good cards,” Jack London is famously supposed to have said, “but sometimes playing a poor hand well.” Ralph Martin had neither. Instead, he was playing someone else’s cards when he successfully launched the first powerboat poker run in 1985. His idea—along with his partner, Norville Stahly—was simple: Take what motorcycle clubs had been doing for decades and apply it to go-fast boats. The players? Clients at Everglades Marina in Ft. Lauderdale who were, for the most part, either too timid to leave their home waters or unsure how to navigate to distant shores. The group dynamic offered an assurance that no location was too remote, and having mechanics on call certainly didn’t hurt either. Their first poker run from Ft. Lauderdale to Marathon in the Keys drew 20 boats. The next year the entrants doubled.

Showmanship was baked in from the beginning. Stahly wasn’t known for his subtlety, naming his white 38-foot Cigarette The Dealer and splaying a royal flush on the side. (A 1986 article in South Florida’s Sun Sentinel laid out the requirements: “If you can’t play a 50-mph straight, you can’t keep up with The Dealer.”) Now, anyone with the right money could conceivably be an offshore racer, enjoying the rush without the high degree of difficulty or danger. The sport attracted supermodels, real estate tycoons, athletes, oil barons, out-of-towners desperate for some action and a who’s who of celebrities, from Hulk Hogan and Hugh Hefner to Sir Richard Branson. By the turn of the 21st century, over 100 poker runs were being held across the country, attaching various causes and charities to somewhat legitimize the carousing.

The sport’s nucleus remained in South Florida—as did a contingent of drug runners. But unlike offshore racing, which had the stigma of drug running attached to it, by the time Stu Jones held his first poker run, in 1991, the steady flow of drugs into the Port of Miami was all but curtailed. Boatbuilders caught or implicated in smuggling usually had their assets seized. Or they flipped, and started building go-fast boats for the government. One was the original founder of Midnight Express, Byne Goode, who pleaded guilty to laundering drug money and, as punishment, was sentenced to build a series of boats for the DEA. In the growing sphere of poker runs, drug runners had effectively become persona non grata.

With the Glaser family acquiring Midnight Express in 2006, their high-performance boats—a 34-, 37-, 39-, 43- and now 60-foot center console—have come to be a staple in the FPC poker run series. Today, the company’s drug smuggling notoriety exists as a relic of a bygone era, even if the name still conjures images of a saltwater cowboy moving illicit cargo in the dead of night. Glaser tells me one of his employees recently gave him a belt buckle with the company’s original logo, along with the quote, “When you absolutely have to get across the Gulf no matter what.” If a logo was made today, it might read, “When you absolutely have to get to the rendezvous in Bimini.”

“I’ve sold multiple boats from poker runs,” says Glaser. “When we get down to Key West in front of the Conch Republic, where all the parties are, and it’s a total madhouse at all times, people come up to you and want to know more about the boat.” Such levels of interest are a far cry from the days of old, when boaters in Miami, the Keys and beyond would never have imagined—or taken seriously—the idea of a high-performance center console. “Nobody really did,” adds Jones. “Now, that’s all changed.” Today, when he’s not arranging the FPC’s poker run series, Jones is organizing Midnight Express owner rendezvouses to distant, exotic shores. Because isn’t a rendezvous just a poker run without the cards?

Gilbert’s Resort, on a sandy spit beside the Overseas Highway, advertises itself as “the largest tiki bar in the Keys.” When I show up, only a smattering of people are out sunning themselves on lounge chairs on the beach, or sitting in the shade of an enormous thatched grass-roof enclosure, waiting for their Caribbean-style food to arrive. I can’t help feeling like a sunburnt, shoeless, modern-day prophet, comfortable in my knowledge of what’s to come; a prognosticator of raging. In hindsight, I should’ve made a sign: THE PARTY IS NEAR.

At midday, the full occupying force of the Florida Powerboat Club armada descends on the unsuspecting vacationers of Gilbert’s Resort. Revving engines break the still air as high-performance vessels raft up alongside each other, some six or seven deep, jutting out from the open-face dock into Blackwater Sound. I overhear one of the resort-goers mention something about a band. A band? Screw your idea of entertainment, the onlookers and admirers that have appeared out of nowhere seem to say. Ours has already arrived. I come across more than a few people arrayed around the Midnight Express 60, cold beverage in hand and a look of longing on their face.

Little do they know that with this sport, sometimes you get dealt a bad hand. In the case of Team Midnight, an ugly pair of twos: Coming into the Keys the day before, two of the four engines had stalled. As we limped through the mangrove forests, I thought back to how these events have proliferated: as a way for boaters to experience new places and meet new people, using their boat the way it was intended. Pushing your go-fast machine to—or past—its limit. It’s only natural that mechanical issues should arise. It’s two sides of the same coin: to really learn the intricacies of your boat, it takes dealing with the good, but more often than not, the bad. In our case, the fix was a simple one. Seven Marine dispatched a mechanic who swiftly diagnosed and repaired the issue, and we were on our way in no time.

If we had wanted to, the 60’s large, luxurious interior—split between a VIP and a master, with an adjoining head—could have accommodated half our party overnight. With hull number one’s current engine configuration, we could have filled the enormous cockpit hatch with a plethora of toys (in the place of two, 1,200-hp MAN engines that can supposedly push the 60 to a top end of 90 knots). Instead, ice cold Boobies await. The 16-oz., frozen concoction includes multiple spirits and juices, and is a local favorite—with several, shall we say, not-quite-printable variations on the theme. But a portion of each drink sold helps support breast cancer awareness, so bottoms up.

Like a murmuration of starlings or a school of fish, the power of the group dynamic is at times overwhelming, but mostly it’s a spectacle that you can’t help but appreciate. As a group, the boaters kick back, mingle and enjoy the tiki bar’s kitsch atmosphere. Tomorrow they’ll wake up—with some, more than others, a little worse for wear—and do it all over again. Some might find the whole thing a little excessive. But, like the massive super console we came in on, sometimes too much of a good thing is just right.

Gilbert’s Boobie

Gilbert’s Boobie, a $9 frozen concoction mixed with plenty of fruit juices and spirits, is a local Key Largo favorite. That’s because a portion of each guilty pleasure sold helps support Breast Cancer Awareness—so bottoms up! Can you match the name of the libation with the floater that gives it its name?

This article originally appeared in Outboard magazine.