There are two primary seasons in Key West, loosely defined as:

1) Fantasy Fest

2) the rest of the year

For Jetsetting readers out there in search of the ultimate in wholesome family entertainment, we’re pretty sure there’s a mouse up in Orlando that would be better suited. But if you think it won’t warp the kids too badly to be exposed to extreme alcohol intake at all hours of the day and night, revelers of all three genders clad in creatively colorful body paint and little else marching around, and the distinct possibility that you might have to step over copulating couples in the street, by all means come on down to the little island at the end of the road the last week of October.

If, on the other hand, hedonism is not your thing, shoot for a different time of year. Remember that winter is the off season in Key West, when barely a tourist is to be found in the full bore heat of summer. Outside of Fantasy Fest, you’ll find plenty of things to see and do, and even a faint pulse remaining of the pirate town it used to be.

If tacky tourism is your thing – not to worry – there’s plenty of that but why not aim your sights a little higher and set your compass to a few spots that are actually worth the price of admission, even when they’re free.

1. Hemingway House – Home of famous writer/suicide victim, Ernest Hemingway, during what some have called the most creative period in his life, the house is now the primary resident of descendants of his six-toed cats. See the first swimming pool in the Florida Keys and wander the lush tropical grounds. If you have a literary bent at all, give it a shot. If you don’t like books, why not get drunk instead?

2. Fort Jefferson – If you take a jaunt 70 miles west of Key West, accessible only by boat and seaplane, you’ll stumble across a tiny collection of islands, called the Dry Tortguas, that comprise the Fort Jefferson National Park. It would be difficult to find a more serene tropical paradise anywhere, mainly because there has been absolutely no development allowed. The largest of the islands houses a crumbling Civil War fort inhabited by a few park rangers and the ghosts of history. Words can’t do justice to the natural majesty, however, if you don’t like boats, why not get drunk instead?

3. Green Parrot Bar – even those who aren’t into the Duval party scene should spend a hour or so in the Green Parrot. In the words of Playboy Magazine: “The search for the definitive Key West saloon ends at the Green Parrot.” Ensconced on the same street corner at Whitehead and Southard Street since 1890, this sunny place for shady people has been cranking out drinks and great music for well over a century. But if you don’t like bars, why not…never mind.

Key West is a quirky little town, very gay friendly, if that makes a difference to you, that is not everyone’s cup of tea, but it might be yours. Give it a whirl if you dare.

The Jetsetter Show

Flickr / inazakira

Tags: Fantasy Fest, Key West