Promoted as "the most insane athletic showdown on Earth," the Florida Man Games poke fun at the state's reputation for brawling, drinking, gunfire, reptile wrangling and other antics carrying a risk of time in jail or intensive care.
A dozen teams will take part in the debut event in St Augustine, with contests and sideshows inspired by real events from the state.
To train for the games, Larry Donnelly, 42, rode a bicycle around his neighbourhood with a second bike strapped to his back. His event Saturday: a race requiring competitors to switch between bikes while toting a catalytic converter and a handful of copper pipes, common items in Florida theft stories.
Other events involve contenders wrestling sumo-style while holding pitchers of beer, or running from actual sheriff's deputies while jumping fences and avoiding obstacles. Others face a scramble to grab cash flying in simulated hurricane winds.
Organiser Pete Melfi said he expected more than 5,000 spectators paying $45 or more per ticket to join the fun at the city's Francis Field.
"We kind of give a person an opportunity to live a day in the life of Florida man without ending up in a cop car," said Melfi, who runs the St. Augustine media outlet The 904 Now.
But he had to tone down some racier aspects of the Florida Man mythos to obtain a permit.
"There's typically drugs and nudity," he said. "But the city frowned on it when I asked for drugs and nudity."
The "Florida Man" phenomenon seeped into the nation's conscience thanks in part to a Twitter account that started in 2013 with the handle @-FloridaMan. The account touted "real-life stories of the world's worst superhero," sharing news headlines such as "Florida Man Bites Dog to 'Establish Dominance'" and "Florida Man Tried to Pay for McDonald's With Weed."