The Playpen attracts young, wealthy partiers throughout summer, but the Boat Party (August 4–7 this year) brings out the biggest crowd—sometimes 800 crafts, according to the city’s tourism office. At one point, the affair almost splashed into Indiana. Ted Widen, publisher of now-defunct Chicago Scene magazine, started the loosely organized event 17 years ago, and it has outlived the publication. In 2011, according to the Chicago Reader, the city tried to make Widen apply for permits and get insurance, and the thought of red tape acted as a buzzkill. He considered relocating to Indiana, but instead just canceled the event. The boats showed up anyway. Now, Widen chooses a mid-summer date and puts a flyer online, and the booze-cruise-in gets raging by noon. A stripper pole is a fixture.
Sound like your scene? A website called Boatbound rents watercraft for the day on the peer-to-peer model—we suggest anteing up for a captain.