Welcome to the Playpen: Chicago’s Labor Day yacht hotspot turns into floating circus of Elvis impersonators, pole dancers and steamy rendezvous

It’s the last weekend of summer for Chicagoans hellbent on squeezing every moment out of their all-too-fleeting party boat season.

Here in the surprisingly turquoise waters of Lake Michigan lies a unique hotspot, an area where boaters anchor in the shadow of this city’s iconic skyline to revel in each other’s company.

It’s called the Playpen.

For many regulars, the three-month, often hedonistic and sometimes hazardous, social scene from Memorial Day through Labor Day mitigates the nine months of rain and snow for which the Windy City is notorious.

‘Summers here are crazy short. There’s definitely beauty in things that are so temporary,’ says Liam Poczatek, a captain who grew up boating Chicago’s expanse of Lake Michigan and runs the only water taxi service to and from the Playpen.

Leah Paskero, an exuberant dental hygienist, spends every summer Saturday bobbing on the water, greeting boaters with her megaphone:

‘I live for the Playpen. It’s my social life. Without it, I could never stay in this city.’

Anywhere from 100 to 500 boats, ranging from small skiffs to 90-foot luxury yachts, anchor here on sunny summer weekends.

Motorboats come loaded with frat brothers and kegs.

Charters, complete with dance floors, bartenders and pole dancers, bring people celebrating milestone birthdays and bachelor parties. One boat called The Flying Lady was rigged with a trapeze, but stopped showing up a few years ago.

A few Speedo-wearing old geezers pack their private powerboats to capacity with bikini-clad twentysomethings in hopes that one might take her top off in appreciation for her afternoon on the water.

Some boaters anchor off to the side, away from blaring subwoofers, for some wholesome family togetherness.

On one yacht this weekend, four generations of a Mexican-American family sang Tejano Music while passing around plates of tamales. On another, an aproned woman grilled kielbasa for grandkids who played rock-paper-scissors for the last pierogi.

Some boats are piloted by professionals like Bob Bloome, a retired Chicago fireboat veteran and former Elvis impersonator who showed Daily Mail the ways of the Playpen on his charter boat, Michigami, on Saturday.

Others are operated by amateurs without captains’ licenses, let alone any nautical experience. You need only a driver’s license to rent a boat.

‘I’ve seen so much insanity on the water that nothing amazes me anymore,’ Bloome says.

The Playpen is at its busiest during special events such as Black Yacht Weekend and the Chicago Scene party in June, and as a place to watch fireworks on July 4 or Chicago’s Air and Water Show in August.

On hot summer days, owners of flyboards flit from boat to boat giving passengers – especially young women in string bikinis – free hydroflights powered by the lakewater.

Young staffers at a nearby Gold Coast tech firm come to hold meetings on a ‘lilipad’ raft attached to the back of their boss’s yacht.

And graduates of a nearby law school chartered a boat to the Playpen after their bar exam in July, asking the captain to forgive their hard-earned debauchery.

‘We have a lot of fun out here. But we don’t share the details with reporters,’ says Cam Schwartz, 28, who was celebrating a buddy’s birthday on a charter boat called True Therapy IV when he dove off and swam to ours for a tipsy interview.

‘In Chicago, you gotta get on the lake before it gets cold out,’ he tells us. ‘Let people know this is the greatest place on the planet.’

Known among outsiders more for its sports, architecture and pizza, Chicago is a great boating city with the biggest harbor system in the US.

The area now called the Playpen was formed in the early 1900s when the city and Army Corps of Engineers built two breakwaters north of where Navy Pier now stands to protect a stretch of lakefront along Lake Shore Drive. 

Those concrete walls about 400 yards from shore keep the water here relatively calm and offer a presumably safe place for boats to anchor just blocks from the famed Chicago Water Tower and John Hancock Building.

Some boaters here, especially novices, like to tie their vessels to each other, forming a flotilla anywhere from two to 40 boats long. 

Partiers often hop from boat to boat in search of better food or drink, or better-looking potential hook-ups, than they came with. In unison, they dance to whatever tunes are blaring from the boat with the loudest speakers.

As longtimers tell it, things ran relatively smoothly until the Covid pandemic five years ago, when scores of Chicagoans bought boats and headed to the Playpen, a federal anchorage area without social distancing regulations. 

Entrepreneurs rushed to form charter businesses that, under US Coast Guard rules, should require customers to hire licensed captains to pilot boats carrying 12 or more passengers.

‘But most don’t,’ says Brady Ruel, a native Chicagoan now in his 25th summer captaining charter boats off the city’s shoreline, most of which are filled with people mainly wanting to experience the Playpen.

Even in its calm waters, boating here can be tricky given the hundreds of boats, jet skis, rafts and swimmers crowded into a tight area. 

Nautical inexperience, often exacerbated by boaters drinking, snorting or shooting up whatever spirits or drugs happen to be on board, can lead to trouble.

‘For some people, getting drunk, getting wild and out of control is their main interest out here,’ Capt. Bloome says.

Dani Uzelac, a nurse and founding partner of a charter and captain training company called Boat Safe Great Lakes, recalls hosting a bachelorette party attended by women whom she says looked like supermodels.

‘Every man in the Playpen was trying to swim to our boat, including one guy who was trying rather unsuccessfully to swim with a magnum bottle of vodka in his hands. Somebody on a jet ski had to save him,’ she says.

Many boaters don’t know how to anchor, leaving their vessels to drift into swimmers, smash into other boats and even crash against the concrete breakwaters.

Some passengers dancing or sunbathing on boats can lose their balance from wakes caused by jet skis or other watercraft driving too fast nearby.

Others dangling their feet off boats or hopping from one to the other can get caught between them or hurt by underwater propellers that can slice off fingers and toes in an instant.

In 2022, two women on a raft tied behind a yacht were gravely injured after another boat backed into them. Both were pulled underwater and toward their propellers, which severed one woman’s hand and cut off the other’s legs below her knees.

‘If there are no injuries, then you didn’t have a good time!!!! Gen X,’ reads one particularly apt social media post written after that accident.

‘It seems like every weekend there’s some sort of emergency where someone needs rescuing,’ says Walker Greenlee, who hosts friends aboard his powerboat, Spanky and the Gang, almost every Friday, Saturday and Sunday each summer and is a stickler for safety.

In several instances, people who own or operate boats in the Playpen have ended up in the water, leaving passengers unable to drive or even call for help because they didn’t know where the radio was.

Overloaded or ill-balanced vessels have capsized. Boats have caught fire and sunk.

‘We find them two weeks later, fish having chewed the eyeballs out of people’s heads,’ says Capt. Bloome, whose 28 years working on a Chicago Fire Department rescue boat led to countless Playpen horror stories.

Because online reviews greatly affect charter boat companies’ business, many are reluctant to cancel trips in bad boating weather.

Several boats have run into trouble navigating Lake Michigan’s rough and often unpredictable waters on their way to or from the comparatively calmer Playpen. Waves as high as nine feet roiled off Chicago’s shore as recently as last week.

‘This lake can be a raging tempest at any moment,’ Bloome says.

In June, Zahrie Walls, a 27-year-old hairstylist in Chicago, was a guest on a boat trip that coincided with the Playpen’s Black Yacht Weekend. There were especially strong currents that afternoon, and she fell into the water without a lifejacket. Her body was found and pulled from the lake a few hours later.

‘She doesn’t know how to swim,’ says her mother, Kizzie Walls, who still speaks of her late daughter in the present tense.

‘They didn’t give any safety guidelines. They didn’t do any of that. And nobody was criminally charged,’ she adds. ‘This Playpen, it’s every parent’s nightmare.’

‘The bottom line is that people with little boating experience have no business turning boats into nightclubs,’ adds Dave Benjamin, the co-founder and executive director of the Great Lakes Surf Rescue Project, which promotes safety on all five Great Lakes, including Lake Michigan.

He estimates that 46 to 50 deaths are reported each year on the lake – a number he thinks is intentionally lowballed by communities hoping not to scare away tourists.

In response to Zahrie’s drowning, a city alderman has proposed an ordinance requiring boaters to wear life vests on boats operating off Chicago’s shore. 

Although most professional boaters agree the measure is needed, they also expect it will make little difference because the city has scant resources to enforce it and because the Playpen falls into federal, not city, jurisdiction.

Several Playpen regulars have, in the meantime, opposed the ordinance on grounds that lifejackets would mess up their tan lines.

There’s an aspect of the Playpen culture that is hyper-sexualized, including a Wheel-of-Fortune-type game on one yacht in which spinners may be required to flash or moon other players. 

Several regulars have told us they’ve seen boaters having sex in full view of others.

As Poczatek tells it, there’s also a transactional nature to the scene.

‘I get a lot of girls on my boat asking me to set them up with a guy with a boat, any guy, no matter what he looks like,’ he says. ‘I also get girls who feel trapped or unsafe on certain boats, and call me to go get them.’

Poczatek has ended up pulling more things from the water — from litter to people drowning — than he bargained for when setting up his water taxi business five years ago. He and other boating professionals are irate that ‘So many people driving boats around here seem clueless about putting people’s lives in danger.’

Capt. Bloome turns 67 this week and plans to spend the day on his yacht without any customers. We ask if he’ll be heading to the Playpen.

‘No way,’ he says. ‘Not my cup of tea.’