What It's Like to Live in Key West

Travel to the country's southernmost point and discover what it's like living on island time.

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.

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