The old salts of the shrimp fleet have been undercut by Asian shellfish farmers. Flower children who hitchhiked here in the '70s have taken their beads and tambourines back north. But the Conch Republic is losing more than just its slackers, hippies and self-styled pirates.
Teachers and firefighters, grocery clerks and bank tellers, hotel maids and falafel fryers - all are leaving Key West, unable to pay rents and mortgages twice as high as on the mainland. At least 14 percent of those younger than 55 have left in the past few years.
"I'm a sixth-generation Conch, and I don't know if I'll be able to stay here," said Millie Bringle, 26, who manages a real estate office by day and tends bar by night.
For five years, Bringle and her husband, a firefighter and electrician, have worked four jobs between them to keep up with a $450,000 mortgage on the tiny house they built on a mobile-home lot. Now they are divorcing and have to sell, and Bringle isn't sure where she'll land.
Much of Bringle's family has left, even those who bought their homes in the days when trailer parks far outnumbered oceanfront townhouses.
Monroe County has lost more than 2,000 workers since the 2000 census. That's a blow to the service-oriented economy in a county with 75,000 residents and 2.25-million overnight visitors a year.
"We have a shrinking population - one of the few places in Florida going in reverse," said Ed Swift, owner of the Conch Tour Trains, which thread the narrow streets of the historic Old Town.
Swift's trains are full of day-trippers from the cruise ships that have replaced the shrimp fleet at the seaport. "Whether it's the teaching profession or the hotel business, we have a critical shortage of qualified people."
An employer of 300, Swift had to move some of his operations to St. Augustine because he couldn't find local workers torepair and maintain the tour trains.
The dearth of workers has put strains on the upscale establishments patronized by the swelling ranks of the wealthy.
Pisces Restaurant serves French-Caribbean seafood in the blue-and-yellow decor evocative of Provence. Its waiters can present lobster and crab concoctions to diners in Russian, Spanish, German and French. The cosmopolitan flourish is born of necessity rather than design: Manager Tyler Scott has to sponsor foreign workers for temporary stints of up to six months to make up for the local labor shortfall.
And it's not a solution for most Key West employers.
"Because we're high end, we're able to attract them," he said. "The employers who are hurting are those like CVS and Kmart. It can take you half an hour to pay for something there, because they don't have enough workers."
Suzy Murphy, who owns Island Oasis B&B, often has to clean the six guest rooms herself because any kind of help is hard to find.
"They have a saying here that if you show up one day, you're hired; if you show up a second day, you're the manager," she said with exasperation as she set out the breakfast buffet.
While the high-end hotel stock grows, working-class rentals are being replaced. More than 2,400 mobile homes have disappeared from the Keys since 1990.
Second homes, for buyers who leave homes empty between visits, have replaced them, said Ned Murray of Florida International University's Metropolitan Center.
"Monroe County now has a 38 percent vacancy rate, which is shocking," Murray said.