Key West, the Gentler Side

Key WestKey West – Imagine a city built on shipwrecks, fishing, smuggling and shrimping. Now imagine a nearby living coral reef, streets lined with Bougainvillea, poinciana, frangipani and other exotic tropical flowering plants. Imagine a historic city center where there are more preserved century-old buildings than you can count. This is Key West. Think of the end of the road for all sorts of colorful types over the decades who’ve headed south to escape the real world. These types bring their charm to the city, charm from seedy characters, dreamers, and eccentrics plus just regular folk who love to fish an awful lot. One thing they all have in common is a laid-back lightheartedness and a don’t ask don’t tell, open-minded attitude. Key West has been amassing its fascinating history, colorful characters, and fancy architectural surprises now for more than 150 years. It’s now a one-in-a-million city comprised of all these elements, plus the effects of over half a million visitors each year. There really is no place like Key West!

Who Lives in Key West?

U.S. Navy

Besides all the zany transplant characters mentioned above, Key West has a long-standing resident population who’ve lived here for generations. Key West also has a close relationship with the Navy, whose presence here dates back to 1822, when Lt. Matthew C. Perry arrived here to see if Key West would be good spot for a base. It looked like the real deal to Perry, and soon after that Key West got its own Customs House and the Navy set up shop. In the 1930s, the Navy grew by leaps and bounds, and a submarine base provided lots of jobs for locals. Even though it (the sub base) closed in 1974, there’s still the Naval Air Base which provides lots of jobs for locals. Today, the US Navy owns much of the waterfront property in Key West, even though they’ve begun selling it off, bit by bit. Navy soldiers account for much of the population here, even after withdrawal of some of the Navy in the 1980s.


More ships came to Key West following arrival of the Navy, since now they could unload cargo here. It was now an official U.S. port of entry, drawing all sorts of cargo ships. The reef started to play a bigger role in the city’s transformation. Bad navigation and stormy weather caused lots of ships to wreck on the reef, and the 1800s saw a boom in the salvaging industry of Key West. Now the citizens were getting richer and richer, and eventually would be the richest city in the United States, in the mid-nineteenth century.

Cuban Cigar Makers

At the same time, Cuban cigar makers were arriving in Key West in droves. There were over one hundred cigar shops in Key West by the beginning of the twentieth century. Some got rich and built large homes. One of these former cigar mansions is now an inn, called the Southernmost Point Guest House, at 1327 Duval Street. It’s a grand old Victorian and one of the nicest places you can stay at in Key West.


In the 1920s, when the United States was going through its Prohibition era, Key West was a major base of operations for beer and liquor smugglers. Beer came from Cuba, as did rum. The British Isles kindly sent whiskey, rye and scotch. After the close of this era, Key West was again a smugglers’ base forty years later, only this time the contraband was marijuana. Lots of people became rich this way, but it started to end in the 1980s, when crackdowns began.


Today, Key West has a lot of people involved in tourism living here. In fact, this is now a tourist town, and in a way it always has been. People have come here to sample Paradise for decades. There’s also a large homosexual population here, thanks to a progressive and open-minded strain that runs through the community of Key West. Chic guest houses, gourmet restaurants & bars, shops, spas and artistically restored conch houses can be attributed partly to the long-standing residents who’ve remained in Key West over the decades.