As the topographical tail of the United States, Key West dangles off the end of the Florida Keys chain, an island of unfettered freedoms and capricious charms.
It is a nonchalant, end-of-the-road kind of place where people who never want to grow up feel right at home. It is crazy, indulgent, uninhibited and hip, full of small town gossip and big city panache.
The city’s architecture a blend of Spanish, Bahamian, New England and Southern is world famous, with grand tropical mansions adorned with gingerbread railings dotting even the most ordinary of streets.
The resident population a combination of old Conchs, rich yuppies, middle-class families, Cuban immigrants, Bahamians, military employees and gays totals about 25,000, but when you add the million tourists who visit each year, the island can feel very crowded.
The gateway to Key West is Stock Island at MM5, once a sprawling cattle corral but now a busy hodgepodge of landmarks.
There’s the Key West Golf Course, the Tennessee Williams Fine Arts Center, and the eyesore known as Mount Trashmore, a colossal garbage heap.
Stock Island also has a fleet of shrimping boats, run by some unsavor characters, and the Oceanside Marina on Maloney Avenue where you can find some first-rate charter fishing boats.
Crossing Cow Key Channel at MM4 you come to a confusing fork in the road.
To the left is South Roosevelt Boulevard or Highway AIA, which leads to Key West International Airport and beaches.
To the right, lined with discount shopping center and fast-food restaurants, is North Roosevelt Boulevard, the main road that leads into the heart of Key West, which is known as Old Town. When North Roosevelt Boulevard turns into Truman Avenue you’ll see a large sign reading “Downtown” which means Duval Street.
Turn right, and you will coast into America’s mecca for misfits, Key West.
InsideMiamiBeach.com, a Cool Guide to South Beach.