What It's Like to Live in Key West

On the southernmost point of the U.S., discover what it's like living on island time.

By: Nancy Klingener

White Bungalow with Blue Accents in Key West

White Bungalow with Blue Accents in Key West

Key West, Fla., has a lot of nicknames. There’s Cayo Hueso, the original Spanish name, which translates to Isle of Bones or Bone Island. There’s the Last Resort — a name with many meanings for a drop of land at the end of an island chain that has served as an escape for generations. For 21,000 people it is simply home, the place where they live, work and play.

Key West prides itself on being different from the rest of America. Much of the difference derives from simple geography. Key West is located at the end of the Florida Keys, an island chain that stretches more than 100 miles south and west from Miami.

Forty-two bridges link the Keys and almost everything — including power and water — is brought in from the mainland. That means most goods are more expensive and others are simply unavailable.

Key West was initially developed in the 1820s as a base for Bahamian shipwreck salvagers — and U.S. Navy ships that were chasing pirates in the region. When a series of lighthouses made the reefs safer for shipping, the island turned to cigar manufacturing for its fortune, prompting an influx of immigration from Cuba in the late 19th century.

In 1912, oil magnate Henry Flagler finished the Overseas Railway, linking the island to the mainland for the first time. The railroad was destroyed by a Category 5 hurricane in 1935, but was quickly replaced by the Overseas Highway, U.S. 1, which continues to connect the Keys today. Key West was desperately poor during the Depression, so poor that the city declared bankruptcy and turned itself over to the state of Florida. The state considered simply closing the place and moving the remaining residents elsewhere, but instead called in a federal New Deal project to remake the island as a resort.

The concept didn’t quite take on the first try and World War II rescued Key West, which became a bustling Navy base. But in the 1970s, when the Navy closed most of its operations, the tourism idea was revived. With new, wider bridges replacing the old ones from the 1930s and a new, bigger pipeline bringing more freshwater, Key West boomed again.

Along the way, Key West established its continuing character. Like many places that are isolated from traditional authority, there is a high tolerance for lifestyles and activities that would be frowned upon in more conventional places. The place has a nonjudgmental, live-and-let-live ethos. Key West, like Provincetown and Fire Island, welcomed the gay community decades before being out was accepted in the rest of America; the city elected an openly gay mayor in 1983. Writers, artists and eccentrics of all stripes feel comfortable here.

The island currently relies on tourism as its primary industry, with contributions from the military — there’s still a naval air base on an island five miles up the Overseas Highway. With scarce resources available, the island has reinvented itself throughout its history on a regular basis.

The locals — people who are born here — are called Conchs (pronounced konk) after the sea mollusk. Their numbers are constantly replenished by a stream of people from elsewhere, people who fall in love with the island despite the expense, the heat, the occasional hurricane and the distance from mainland amenities.

As a tourist town, Key West sells itself on its warm climate, outdoor activities like fishing and diving and its historic architecture. But for locals, the draw is the people and the possibility of reinventing and defining yourself in a place where almost anything goes.

“The incredible mix of totally different and seemingly opposite types creates an eclectic local community that works in spite of the differences,” says Michael Blades, a 20-year resident who is the logistics director for RPM Nautical Foundation, a marine archaeological nonprofit.

Vicki Roush, a singer and actress who works as a wine and spirits consultant for Premier Beverage Company, arrived in 1979 and says, “I couldn’t afford to leave once we’d stayed a few weeks.”

“Mostly no one cares about your social, economic, ethnic or religious status,” she says. “You could be sitting next to a wealthy starlet one day — done it — or a con man wanted in five states the next — done that, too. Most people don’t really care about your past.”

For some, it’s stifling — the close living that can feel like a lack of privacy and the inability to simply go to the grocery store without seeing people you know. For others, it’s the perfect situation: a small town that is casual and nonjudgmental — and never, ever boring.

So what's it really like to live in Key West? Read on to learn how locals have adapted to this unique area.

Key West is full of history, tradition and a unique character unlike anywhere else in the United States. 


Key West is, literally, small — usually referred to as three-by-five miles though the island is kidney-shaped so it depends on how you measure it. It’s also flat and warm yearround. Parking is at a premium and gasoline, like everything else, costs more here, often 20 cents more per gallon than on the mainland. For many, especially working people, bicycles are essential for everyday transportation.

“When I moved here people told me I was going to need a bike. I kept imagining the guy in the tight shorts and helmet, hunched over and racing top speed,” says Landon Bradbary, who moved to the island from New York City in 2002 and manages the Alexander Palms Guesthouse. “What I didn’t realize is that the beach cruiser is alive and well in Key West. My first bike was a $30 toss-off. My second bike is named Jennifer. She’s a Green Fuji Tango. I’ve had her ever since.”

The historic district, known as Old Town, was built before automobiles in a dense urban design — the island was even smaller then, as much of the more recently developed area, known as New Town, was made by filling in wetlands. That means many Old Town homes are squeezed close together and don’t have driveways, requiring car owners to park their cars on the street. They wage constant battles with visitors and workers who drive in from New Town or farther up the Keys, where housing is cheaper. Many locals drive older cars that are dinged from being parked on the street or faded from the sun — these are referred to as “Conch cruisers.” Others ride scooters, which are cheaper and easy to get around town, even if they don’t carry many groceries or protect you from the rain.

The city has a bus system that is seeing increasing use but is still not well understood or particularly convenient.

Transportation in Key West can be tricky, so many locals and tourists forgo their cars and opt for bikes or scooters instead. 


As you would expect on an island with a limited supply of housing and demand constantly replenished by newcomers entranced by the idea of living in paradise, housing is expensive. Before 2005, it was heading for the stratosphere. It wasn’t unusual to see a one-bedroom condo sell for $500,000 -- and the Floridian addiction to real estate speculation was in full force. But in 2004 and 2005 the island was grazed by a series of hurricanes, capped by Hurricane Wilma in 2005, which sent floodwaters across most of the island and caused millions in damage. Then the recession hit and the foreclosures began.

Recently the market has begun to stabilize though prices continue to decline. In 2010, the average sales price for a home in Key West was $423,000, 8 percent lower than 2009. If you want to live here, and aren’t trying to sell you home, that can be good news.

“When we moved here we never dreamed we’d be able to own a home. But after everything crashed, we were able to get our foot in the door,” says Landon. “We looked for almost eight months and it was pretty depressing. People with a lot more money than us were snatching up places in our price range. Finally it just happened. We came upon this wacky, multicolored clown house. We jumped on it with every intention of repainting it. It’s now been a year and I just tell people that we live in the house that looks like an Easter egg.”

Living in Key West — and especially the longterm commitment of owning a home — means you’re forced to reach accommodations with your neighbors. Key West differs substantially from modern neo-traditional communities — some of which used it as a model — like Seaside and Celebration — in that homes of very different income levels and upkeep are on the same block.

“It’s living cheek-by-jowl with millionaires on one side and a family of fishermen on the other,” says Dianne Zolotow, who grew up in Key West in the 1950s and moved back to the island in 1988 after living in New York, San Francisco, Washington D.C. and Boston. “The neighbors live close enough to hear you sneeze and are polite enough not to appear to be listening.”

And the density has its advantages. “We chose our house to be within walking distance of everything we love: the downtown restaurants, the library, the movies, the locally owned grocery stores, bakeries, bars, and the Monday organic veggie market,” Dianne says.

The subtropical climate means constant upkeep, especially on the historic wooden homes that are susceptible to rotting and termites. The designation of Old Town as a historic district means renovations are tightly regulated; all development in the district must be approved by the city’s Historic Architecture Review Commission, right down to the paint on the shutters. That doesn’t, however, seem to limit the creativity of Key Westers who find ways to make their homes individual with artwork, yard decorations and plantings that grow year-round and have an unnerving habit of taking over seemingly overnight.

The subtropical climate of Key West makes it an ideal location for retirees and those looking for a more relaxed lifestyle. 


Finding something to do in Key West is never a problem. In fact, the opposite is true, especially in “season,” the period from Christmas to Easter when snowbirds are in residence and tourism is at its height.

The tourism industry drives the island economically and spans a huge range, from bars like Sloppy Joe’s, famous as the one-time haunt of Ernest Hemingway, to more high-end locations like nine one five and the Orchid Bar.

Locals tend to avoid the tourist scene, based largely on the main drag of Duval Street, and find watering holes off the beaten path, like the Green Parrot. But they eagerly support the cultural institutions such as the independent Tropic Cinema, the island’s two theaters, the Red Barn Theater and the Waterfront Playhouse, and the relatively new Studios of Key West, which offers working space for local artists as well as workshops and residencies for visiting artists.

“Going out to consume culture is what it’s about for so many in Key West,” says Vicki. “I love doing that, too. But my preference is to produce the culture, and the opportunities for that are only limited by my real-world commitments.”

Landon manages a guesthouse, and tends bar one night a week — but he also did a few seasons as Frankie, host of the Key West Burlesque, a troupe that started about five years ago and has increased in popularity every year. “You can come up with a good idea, find some performers, and do it all yourself,” he says. “Painters, photographers, dancers, actors, you name it and we have an outlet for it here. If not, the town is often receptive to something new.”

The literary history of the town is legendary — not only Hemingway but also Tennessee Williams, Elizabeth Bishop and many more have called the island home. It continues to draw successful writers, including, in recent years, Judy Blume and Meg Cabot. And the island’s literary heritage is celebrated and furthered each year by the Key West Literary Seminar.

When they’re not consuming culture, Key Westers are often consuming food or alcohol — or both. The island’s local cuisine is heavily influenced by its proximity to and relationship with Cuba. Cuban favorites like picadillo and ropa vieja are standards at Conch family gatherings. And for many, the obvious choice is seafood. Shrimp, lobster and stone crab are all caught locally and available from local fish houses; reef fish like snapper and grouper as well as oceangoing species like dolphin (the fish also called mahi-mahi, not the mammal!) and tuna are also available.

“Just catch it, fillet it, cook it up with a nice little twist and call it a day,” says Landon. “The fish itself is the star of the show, often being caught just hours before if you know the right places.”

“We have places with white tablecloths, holes, in the wall, everything in between,” says Vicki. “It all depends on my mood — and I take great comfort in knowing I can enjoy just about anything my heart desires at any time of the day.”

There is plenty to see and do in Key West. The restaurant and bar scene is always busy.


Because of the logistics and high demand, Key West regularly ranks as Florida’s most expensive place to live. Even with the recent reduction in prices, buying a home in Key West is a serious stretch for many, especially without easy credit.

Rents haven't dropped much, either, so it’s not unusual to see a studio or small one-bedroom apartment rent for $1,000 a month — plus utilities.

And the utilities are pricey because they, too, are coming from the mainland. Garbage is $26.60 a month. Power, water and sewer all depend on usage but are typically higher than what you’d pay on the mainland. Property taxes are not charged at particularly high rates — but the rates, applied to high property values, mean a sizable bill. A home assessed at $500,000 in Key West will pay $5,582 in property taxes this year (that includes the city, county, school district and other taxing authorities). And the real whopper comes with insurance, especially the wind insurance that all mortgage companies supply. After the multi-hurricane years of 2004 and 2005, the insurance companies started raising rates considerably.

Locals gripe about the cost of living and the expenses incurred by local government — but once they’ve committed to the place, few talk about leaving.

“I once worked three jobs to make ends meet and know many people that still do,” says Michael. “But the question should be what price is one willing to pay to secure the quality of life and community that you get in Key West? I think it’s worth every cent.”

Locals also love to gripe about the tourists who clog traffic, create lines at restaurants, incessantly beep the horns on their rental scooters and cross streets without looking for oncoming traffic. But the locals find a way to accommodate them.

“I let them remind me, every day, why I live here,” Landon says. “They work all year long to save up the money and time to just spend a few days in a place that I get to see each morning when I wake up.”

And the real locals — the ones who are here year round — start to look forward to summer, even with its unrelenting stickiness and occasional threat of hurricanes.

“When season is over, we take back the streets and the seats at the bar,” Dianne says. “I love going out in September and October when the restaurants and bars and galleries are spiffed up and staffed up, preparing for season. And the water is clear and calm.”

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