Situated 150 miles from Miami, 90 miles from Havana, and an immeasurable distance from sanity, this end-of-the-line community has never been like anywhere else. Even after it was connected to the rest of the country—by the railroad in 1912 and by the highway in 1938—it maintained a strong sense of detachment. The United States acquired Key West from Spain in 1821, along with the rest of Florida. The Spanish had named the island Cayo Hueso, or Bone Key, after the Native American skeletons they found on its shores. In 1823, President James Monroe sent Commodore David S. Porter to chase pirates away. For three decades, the primary industry in Key West was wrecking—rescuing people and salvaging cargo from ships that foundered on the nearby reefs. According to some reports, when pickings were lean the wreckers hung out lights to lure ships aground. Their business declined after 1849, when the federal government began building lighthouses.
In 1845, the army began construction on Ft. Taylor, which kept Key West on the Union side during the Civil War. After the fighting ended, an influx of Cubans unhappy with Spain's rule brought the cigar industry here. Fishing, shrimping, and sponge gathering became important industries, as did pineapple canning. Throughout much of the 19th century and into the 20th, Key West was Florida's wealthiest city in per-capita terms. But in 1929, the local economy began to unravel. Cigar making moved to Tampa, Hawaii dominated the pineapple industry, and the sponges succumbed to blight. Then the Depression hit, and within a few years half the population was on relief.
Tourism began to revive Key West, but that came to a halt when a hurricane knocked out the railroad bridge in 1935. To help the tourism industry recover from that crushing blow, the government offered incentives for islanders to turn their charming homes—many of them built by shipwrights—into guesthouses and inns. That wise foresight has left the town with more than 100 such lodgings, a hallmark of Key West vacationing today. In the 1950s, the discovery of "pink gold" in the Dry Tortugas boosted the economy of the entire region. Catching Key West shrimp required a fleet of up to 500 boats and flooded local restaurants with some of the sweetest shrimp alive. The town's artistic community found inspiration in the colorful fishing boats.
Key West reflects a diverse population: Conchs (natives, many of whom trace their ancestry to the Bahamas), freshwater Conchs (longtime residents who migrated from somewhere else years ago), Hispanics (primarily Cuban immigrants), recent refugees from the urban sprawl of mainland Florida, military personnel, and an assortment of vagabonds, drifters, and dropouts in search of refuge. The island was once a gay vacation hot spot, and it remains a decidedly gay-friendly destination. Some of the once-renowned gay guesthouses, however, no longer cater to an exclusively gay clientele. Key Westers pride themselves on their tolerance of all peoples, all sexual orientations, and even all animals. Most restaurants allow pets, and it's not surprising to see stray cats, dogs, and even chickens roaming freely through the dining rooms. The chicken issue is one that government officials periodically try to bring to an end, but the colorful fowl continue to strut and crow, particularly in the vicinity of Old Town's Bahamian Village.
As a tourist destination, Key West has a lot to sell—an average temperature of 79°F, 19th-century architecture, and a laid-back lifestyle. Yet much has been lost to those eager for a buck. Duval Street is starting to resemble a shopping mall with name-brand storefronts, garish T-shirt shops, and tattoo shops with sidewalk views of the inked action. Cruise ships dwarf the town's skyline and fill the streets with day-trippers gawking at the hippies with dogs in their bike baskets, gay couples walking down the street holding hands, and the oddball lot of locals, some of whom bark louder than the dogs.