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What lies at the bottom of the Playpen, Chicago's floating daytime clubland

As the name implies, this party-hearty pocket of Lake Michigan is notorious for juvenile behavior.

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"I really shouldn't be drinking right now," says Stephanie, a bikini-clad twentysomething sucking down Modelo Especial from a can. "I'm having surgery in three days." The unemployed hairstylist momentarily feigns concern before doubling over with impish laughter. Her smile beams bleach-white against a complexion that's more self-tanner orange than sun-kissed brown. "I'm getting 'em done, again," she explains, giving her breasts two quick squeezes. "I want 'em bigger—triple D, almost an E!"

Stephanie gestures toward the enhanced chest of her friend Kathy, who is also wearing a bikini. Kathy rolls her eyes and lets out an exasperated sigh. "I'm getting mine done smaller," she says, waving a red plastic cup filled with clear liquor. "Too big!"

It's the last Saturday in July, and these ladies are among more than two dozen others getting bronzed and pickled aboard a 46-foot yacht named Verry Necessary, anchored less than a nautical mile offshore between Oak Street on the north and the Jardine Water Filtration Plant on the south, in a pocket of Lake Michigan known to party-hearty boaters as "the Playpen." As the name implies, the area is notorious for juvenile behavior. Protected almost entirely by break walls, the designated no-wake zone demands that skippers slow to a crawl so as not to rock their neighbors' vessels. The relatively still water in the shadow of the city's skyline is ideal for socializing, and on summer weekends the toned and tanned tie together their cabin cruisers and houseboats, performance runabouts and multimillion-dollar yachts, all stocked with booze and high-wattage stereo systems, to form a floating daytime clubland.

Call it River North on the water.

A dancer slithers down The Flying Lady’s stripper pole; no one at the Playpen is camera shy; an aerial shot of the flotilla, courtesy of a drone - JEFFREY MARINI; NICK STOIANOF/NICKVISUALS.COM/FLYINGLADYCHICAGO.COM (AERIAL)
  • Jeffrey Marini; Nick Stoianof/nickvisuals.com/flyingladychicago.com (aerial)
  • A dancer slithers down The Flying Lady’s stripper pole; no one at the Playpen is camera shy; an aerial shot of the flotilla, courtesy of a drone

Today is the Playpen's biggest "raft up" of the year, the Chicago Scene Boat Party, which was started in 2000 by Ted Widen, publisher of the luxury lifestyle mag Chicago Scene. The usual hundred or so Playpen regulars are joined by several hundred more boats packed to capacity with party people raring for the six-hour daylight bacchanal. "Boat Scene," as the event is sometimes called, doesn't have any sense of higher purpose. Its essence is simple and as shallow as a birdbath: see, be seen, get mind-meltingly intoxicated. It's a Panama City Beach spring break come north, except that the participants—many of them professionals—no longer have the undergrad's excuse of youthful indiscretion.

Since 9 AM, the Playpen scenesters have been forming chains as wide as 50 boats, with names like Buoys n the Hood, Martinis and Bikinis, Sea Monkey, Who's Your Daddy, and Honey I Shrunk My Wallet. Many vessels sport six-person "floating island" rafts attached to their tails. And by noon, the designated start, the festivities are well under way. One contingent has already broken out the red funnel beer bong to partake in a liquid lunch. Overhead, a plane whizzes by carrying a banner advertising, of all things, the release of a new Hilary Duff single. Close to the southwest end of the Playpen, Las Vegas DJ Quira is soundtracking the acrobatics of professional dancers Leigh Ann Reilly and Amy Raven, who are taking turns on a stripper pole that's attached to the fly bridge of The Flying Lady, a 60-foot Carver yacht owned by Chicago real estate agent and businessman David Izsak.

Because straight males dominate boat ownership, the access to party hopping in the Playpen tends to be gendered and sexist in ways reminiscent of your average mainstream nightclubs. "Liquor and women, unfortunately, are like currency out here. You've got to have a cute girl or a bottle," says a female real estate agent who frequents the Playpen despite unease with the gender politics of the place. "As a guy, you can drive an itty-bitty boat—as long as you have a bunch of hot bitches, you're fine."

A "flyboarder" captivates the crowd; broing down in the Playpen - JEFFREY MARINI
  • Jeffrey Marini
  • A "flyboarder" captivates the crowd; broing down in the Playpen

Aboard Verry Necessary, a gaggle of women grinding on the stern hoist cups to salute the beefed-out bro bouncing his sizable pecs on beat as DJ Torio pumps out the latest EDM floor fillers. On the starboard side, cheers erupt for the guy suspended 30 feet in the air by a surge of water that shoots from a WaveRunner, through a tube, and into his "flyboarding" jetpack. Everyone agrees he looks like some sort of aqua Rocketeer.

The ship's rear end, meanwhile, is dipping frighteningly low into the water under the weight of too many passengers and a pair of ice chests filled with everything from tarted-up malt liquor to top-shelf tequila and vodka, much of it being consumed by people who haven't eaten today. So it's little surprise to find that by 1 PM, the toilet in the lower level reeks of sour vomit. Near the bathroom door, crammed against a case of Bud Light Mix-a-Ritas, a plastic bin overflows with strappy, bedazzled sandals and high heels that were shed to prevent scuffing the yacht during the dance party. People are shaking ass and pumping fists, but Torio's set amounts to little more than a sustained series of buildups and bass drops. Each time the low end kicks in, a pair of built-in jets around the DJ booth release celebratory blasts of CO2 vapor. Although this happens roughly every 45 seconds, the drunks don't seem to be tiring of the shtick.

Cooler o' booze and bin o' shoes aboard Verry Necessary - JEFFREY MARINI
  • Jeffrey Marini
  • Cooler o' booze and bin o' shoes aboard Verry Necessary

The extravagance of custom CO2 jets seems only slightly less silly when you consider that this particular vessel is co-owned by Chicago and Las Vegas nightlife promoter Brian Pfeiffer, whose company, Surreal, is in charge of getting bodies through the doors of spots like the Mid, Bodi, and Prohibit—places where people practically beg to be blasted with novelty semiliquids. Like other boat-owning nightlife entities that ply the Playpen, Surreal uses Verry Necessary (the extra R in verry "just for the heck of it," Pfeiffer says) as a literal vehicle for boosting attendance at the company's club events. "The yacht is the preparty. You invite the girls and the high-end clients onto the boat, get them to meet each other. Then you take that party to the venue at night," Pfeiffer says. "Hopefully you don't get anyone too wasted on the boat so that they can't come out to the club. Some people just go home and pass out."

But Playpen regulars say the appeal of carousing off the coast is that it feels more exclusive than any old nightspot. Instead of a velvet rope and a bouncer, a vast swath of the lake separates the in crowd from the gen pop. "It's better than a club," says Crystal, an analytical chemist and six-year Boat Scene veteran. "There are no rules out here." Sunning herself on the bow of Verry Necessary, she is suckling from a Tropicana carton that contains a potent punch she has dubbed "the J.Lo," a mix of vodka, cognac, and Irish whiskey topped off with orange and pineapple juices. "Pretty much anything goes on the water. You can wear whatever you want—some people wear nothing, depending on the weather," Crystal says. "And even though the [marine unit] cops are here, they know there are no rules."

Chicago Scene Boat Party veteran Crystal says the bash is “better than a club”; boat scenesters wield red Solo cups. - JEFFREY MARINI
  • Jeffrey Marini
  • Chicago Scene Boat Party veteran Crystal says the bash is “better than a club”; boat scenesters wield red Solo cups.

While it's not entirely accurate to say lawlessness reigns out on this stretch of water, the magnitude of the Chicago Scene Boat Party and the free flow of people inhibit authorities' interference, according to a Chicago police officer who used to frequent the Playpen and was hired as security for Boat Scene. "They try and control it, but by the time it gets to that size it's just so difficult because of the nature of the setup. You have one or two police boats. Everybody's drinking. What do you enforce? It's a good party, but how do you control it? It's really hard."

Hovering on the outskirts of the Playpen, teams from the Chicago Police Department's marine unit, the Fire Department's marine rescue, and the U.S. Coast Guard seem to be playing it cool. If they aren't exactly looking the other way, they also aren't making any noticeable effort to break up anyone's fun. Which is good, because some of these boats are veritable floating pharmacies.

"If you want weed, you can get weed. You want coke, you can get coke. You want Molly, you can get Molly. You can get anything as long as you're tied to the right line," says a CPS teacher finishing a crawl down one of the Boat Scene's many chains.

"There was some guy from Hawaii, and he had all this crazy weed with red tips," the teacher's wide-eyed friend gushes. "He handed me a giant bud, like, 'Here.' And I don't even smoke."

Even as I identify myself as a reporter on assignment, I'm twice offered a "bump" of coke. And yet despite the abundance of illegal substances—not to mention the general nonchalance about openly consuming them—authorities responded to zero drug-, alcohol-, or safety-related incidents during the party, according to a CPD spokesman.

A handful of rather flimsy boating laws seem to aid the debauchery. For instance, vessels on the lake are required to have one life jacket per passenger, and operators' blood alcohol content can't exceed the legal limit, .08, which matches the Illinois standard for automobile operators. But once a boat is anchored, as it would be in the Playpen, those rules don't apply. "We can't enforce OUI [operating under the influence] if the boats aren't under way," says Jared Burkett, operations petty officer at the Coast Guard's Calumet Harbor station.

Another interesting gray area: the Chicago Scene Boat Party doesn't exist in any official legal capacity. "There are no existing applicable permits or licenses required for a 'meet-up' event that is on federal open waters," says Department of Cultural Affairs and Special Events spokesperson Mary May. So the rogue gathering operates without any substantive city regulation.

Aside from binge drinking, the most common Playpen pastimes are ogling and being ogled. - JEFFREY MARINI
  • Jeffrey Marini
  • Aside from binge drinking, the most common Playpen pastimes are ogling and being ogled.

In 2011, the city made a relatively unsuccessful attempt to meddle with Boat Scene. The legal department sent Widen a cease-and-desist letter that said a special-event permit would be required if he wanted to carry out his stated plan to set the record for "world's largest boat party" that year. Untangling red tape wasn't something the magazine publisher cared to do. "They wanted me to get security and, like, a $50,000 insurance policy for the day," he recalls. "Where am I going to get that kind of money?" Widen considered moving the festivities to Indiana, but instead canceled the event. And so he was startled, on the last Saturday of July, to find the Playpen party raging on without him. The festivities had outlived Widen's print magazine, which went out of publication after ten years in April 2011. Since then, Widen's involvement in the annual shindig has been token. "I do absolutely nothing to get ready for it. And I'm not kidding," the 53-year-old says. "All we do is put a date on our website." The location is always "TBA," though it's understood the event will be held in the Playpen.

It's a far cry from the days when the publisher was a sort of two-bit Hugh Hefner and the Playpen served as his waterlogged Playboy Mansion. Widen began partying there during the mid-90s, and once every summer, he and a few friends would circle their boats for a comparatively modest affair. "The problem was there was a small stereo on each boat and everyone was dancing to a different drummer. You'd have one person dancing to 'La Cucaracha' and another person dancing to whatever," he says. "It drove me nuts!" When a buddy purchased a 60-foot yacht, Widen had a thought: "Why don't we get one big sound system and put it on the fly bridge? That way we'll all be dancing to the same drummer."

As the informal gathering swelled year after year, Widen cleverly transformed the event into a marketing opportunity for his then burgeoning magazine. And he profited from the party too, selling sponsorships to the likes of Gibsons Bar & Steakhouse, the British liquor company Diageo, and the Horseshoe Casino. But in 2010 the city began ticketing boats in the Playpen that displayed ads or other signs, which is prohibited near Lake Shore Drive in an effort to curb distracted driving. Now, Widen says, "We don't make any money on it anymore."

At this moment, Widen is standing in an 18-foot jetboat slim enough to thread its way through the narrow flotilla. As the party's figurehead, he feels it's his responsibility to do the rounds. Looking like a politician on a parade float, Widen smiles and waves at old friends, and gleefully flings neon-green frisbees to anyone looking in his direction.

In the commotion of the celebration, Widen zeros in on the familiar face of Dave Lobo, a sort of Playpen superconnector, though he's no club promoter; rather, he has the dutiful air of an Eagle Scout. Lobo owns Wrigleyville's New York Deli and its sister business, Raptor Delivery Service, the only such company that caters to Lake Michigan boaters. Standing in wet socks behind the wheel of his 30-foot Novurania, Special Ops, which bears a decal of an assault rifle, Lobo has spent much of the afternoon ferrying sandwiches to the overserved, underfed masses.

Deliveryman Dave Lobo keeps watch; a Chicago Police Department marine unit boat looms - JEFFREY MARINI
  • Jeffrey Marini
  • Deliveryman Dave Lobo keeps watch; a Chicago Police Department marine unit boat looms

"All the boats wave at me because they know that if they want something I'll get it to them," he says. Lobo's main business out on the lake is food delivery, but he'll make a run for almost anything: ice, liquor, rafts, an air pump. And human cargo too. For $35 a head, he delivers people to and from the Playpen.

Because he spends so much time out on the water, Lobo often has the chance to play hero to a stranded seafarer. "If something goes wrong out here, you don't have a lot of options. You can't park, walk to the store, and pick up what you need." The job has also showed him an uglier side of the Playpen boat parties: when the uninhibited atmosphere leads to a woman being cornered—or worse—and he responds to a distress call.

"Say you're a woman on a boat with 20 guys and you're drinking for six hours. You can always leave a bar. Out here, you're stuck," Lobo says. "There have been times when a girl has jumped off the side of a boat, swam out to my boat, and they've thrown her shoes and purse over to me. What if there was no one there? What if she had to sit there for the next four hours in shame? There always should be a way to get off a boat."

As 6 PM nears, the party at the Playpen slowly begins to break up. It's a delicate operation: first the dinghies and other smaller vessels untie, then the midsize craft, and on down to the yachts, all of which try not to draw Coast Guard attention as they proceed back to shore, toward slips from Montrose to Jackson Park or harbors in Indiana, Michigan, and Wisconsin.

In the sunburned and slurring crowd disembarking at the Diversey dock, a stewed young couple are in deep discussion about what seems to be a Chicago Scene Boat Party romance.

"We just met on the boat," she says. "I think we're in love." She's wearing a short black dress and has bloodshot eyes.

"She may be pregnant though," he says. He's shirtless and holding a cat-print tank top in one hand.

"We kind of banged it out real quick," she says.

"We may get married, though," he says.

She is unmoved.

"Sooo many boats, sooo many people," the girl coos as she stumbles home. "I didn't see any boobs, though. So that was weird."

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