The playground of the rich and famous is home to a crippling housing crisis, one of the highest crime rates in the country, and lengthy daily commutes for workers, all of which have propelled it to the No 1 position in the Forbes.com list.
"Miami has sun and beautiful weather but other things make people miserable. You have this two-tier society: glitzy South Beach attracts celebrities, but the income inequality has skyrocketed in recent years," explained Forbes Senior Editor Kurt Badenhausen.
"Detroit and Flint are struggling," said Badenhausen. "Violent crime is highest in the country in Detroit; housing prices are down 55 percent. Detroit is closing schools and laying off policemen. In recent years they have been demolishing houses to change their city landscapes".
West Palm Beach, Florida and Sacramento, California rounded out the top five cities.
"We're trying to judge cities where residents have a lot of complaints. It doesn't mean that there aren't terrific things there," he said.
And for the haves Miami's charms remain undiminished.
"The one percent in Miami is doing fantastic. But for the vast majority, who make less than $75,000 (a year), Miami can be a challenging place," he said. "Forty-seven percent of homeowners sit on underwater mortgages. That's tough."