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Key West

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.

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 descendants of 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 most 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 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 iconic fowl continue to strut and crow, particularly in the vicinity of Old Town's Bahamian Village.

Although the rest of the Keys are known for outdoor activities, Key West has something of a city feel. Few open spaces remain, as promoters continue to churn out restaurants, galleries, shops, and museums to interpret the city's intriguing past. 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 looks like a miniature Las Vegas lined with garish signs for T-shirt shops and tour-company offices. 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.

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