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 and boogied back north. But the Conch Republic is losing more than just its slackers, aging 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% of those younger than 55 have left in the last few years, cutting into the workforce.
"I'm a sixth-generation Conch and I don't know if I'll be able to stay here," says Millie Bringle, 26, who manages a real estate office by day and tends bar by night at El Meson de Pepe, a boisterous Cuban eatery on Mallory Square.
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 town houses. Despite Florida's 3% cap on annual property tax rate increases, the skyrocketing home prices in the Keys have compounded a traditionally high cost of living, with most goods trucked in over 150 miles from Miami while gas prices routinely hit record highs.
Monroe County, which stretches from this southernmost key to the unpopulated western Everglades, has lost more than 2,000 workers since the 2000 census. That's a body blow to the service-oriented economy of a county with only 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. We have a shortage of warm bodies."
An employer of 300, Swift had to move some of his operations to St. Augustine recently because he couldn't find local workers who could repair 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 wait staff 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 says of servers whose income from gratuities allows them to afford one-bedroom apartments, the smallest of which start at $1,600 a month. "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 An Island Oasis B&B, often has to clean the six guest rooms herself because reliable help -- 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 says with exasperation as she sets out the breakfast buffet on the inn's palm-shaded deck.
She points to new "condotel" developments like the three-story Westin project next door as typical of the islandwide upscaling.
Monroe County froze the number of overnight accommodations a decade ago when the Keys were designated an area of "critical concern" because of fragile mangroves, endangered manatees and protected sea grass.
That encouraged owners of traditional clapboard motels to improve their properties to earn more per unit, or replace old enclaves of funky bungalows with multi-story condos with two- and three-bedroom suites that rent for $500 or more a night.
While the high-end hotel stock grows, working-class rentals are being razed and replaced. More than 2,400 mobile homes have disappeared from the Keys since 1990.
More lavish developments have replaced them, most snapped up by second-home buyers who leave them empty between vacations, said Ned Murray of Florida International University's Metropolitan Center.
"Monroe County now has a 38% vacancy rate, which is shocking," Murray says of the part-time homes. "That tells you that the people who are buying are those who can afford a second home, and those who once were there have gone."
A report just released by the FIU center, which tracks urban trends, puts hard evidence behind anecdotal indications.
Average wages in the Keys are 9% lower than for the rest of Florida, and residents here pay on average more than 50% of their household income to keep a roof overhead, the FIU study noted.
Personal finance advisors recommend spending no more than 30% of monthly income on housing.
For more than a decade, the Keys have imposed a 1% tourist tax on accommodations, goods and services, and committed half the revenue to buying land for middle-class home con- struction.
That has persuaded contractors to put more than 3,000 subsidized homes on the drawing boards, but local officials say the needs are at least three times that number and that the influx of wealthy buyers far outpaces the construction for Conchs.
The pressure to cash in keeps developers concentrated on the seven-figure market.
"The baby boomers are retiring and the successful ones are looking for their McMansions in the sun," says Key West historian Tom Hambright.
He came here with the Navy in the 1960s, when the military and commercial fishing were more important to the local economy than tourists. The counterculture influx of the 1970s mellowed the island's vibe and lured the rum-soaked generation fleeing cold and convention, hedonists who made Ernest Hemingway's watering holes rowdy again and led to new ones like Jimmy Buffett's Margaritaville Cafe.
Some of Old Town Key West's most authentic hangouts, though, have gone the way of patchouli oil and incense.
The Schooner Wharf Bar and the banjo-strumming bands that gathered on the waterfront for sunset concerts have been done in by the Harbor House development, a 32-unit luxury condominium rising on the site of the Old Town landmark.
T-shirt shops and snack bars along bustling Duval Street have closed; designer boutiques like Coach and Little Switzerland have sprouted.
Bringle says she misses the days when her male customers at El Meson de Pepe were mostly mainstream dropouts clad year-round in cargo shorts and flip-flops, their graying hair in ponytails.
"Some of them still wear ponytails and flip-flops," she says of the new locals. "But now that guy on the bar stool in front of me is probably a millionaire."