Historic Old Town district of Key West

Key West Is A Trip, And I’m Not Talking About Travel

Key West is a free-wheeling, hard-partying kind of place that never seems to sleep. It’s the kind of place you come to people-watch. A place where anything goes, as long as you’re not hurting yourself or anyone else. Where else can you see a man drive by on a Harley with an African Green Parrot perched calmly on his shoulder? Where tourists ride bicycles down the main street wearing only swimsuits? Where the taxis have bike racks mounted on their rear bumpers for those who get too drunk to ride their bikes back to their cruse ship or hotel?

Key West bicyclers

Key West bicyclers

Key West Drag Show

Key West Drag Show

Where groups of male cross-dressers, tottering on four inch spike heels, stand in dark, smoky bar doorways, trying to lure tourists inside for a “World Famous Drag Show?” And where people parade around nude, covered from head to toe in nothing more than body paint during the week-long Fantasy Fest?

Words simply can’t do justice to the craziness of this place. It takes photos:

Bar in Key West covered in dollar bills

Bar in Key West covered in dollar bills

Amazingly, no one ever steals the dollar bills line that the walls and ceiling of this restaurant, despite the fact that it is an open-air facility without nighttime security.

Key West Blue Heaven

Key West Blue Heaven

Blue Heaven, located in Bahama Village, is one of the more popular breakfast spots in Key West (above). Here customers enjoy alfresco dining, live island music, and the very real possibility of being attacked by one of the chickens or roosters that freely roam the restaurant, perching on umbrellas (below) or giant sails strung across the courtyard to provide shade.

Roosters roam at will at Key West Blue Heaven Restaurant

Roosters roam at will at Key West Blue Heaven Restaurant

Key West Rum Bar

A bar dedicated to rum and cigars – only in Key West!

The Key West Coffee and Tea House occupies a lovely historic building at the south end of Duval Street, and is a favorite of locals, like this man (below) who comes by each morning for coffee, accompanied by his pet parrot. Note the blue porch ceiling, which is traditional in the tropics. Local lore insists the color keeps insects away, because they are fooled into thinking it is the sky.

Key West Coffee and Tea

Key West Coffee and Tea

Key West Parrot

Key West Parrot

Cops turn a blind eye to the “Scrub Club” an adult entertainment venue that offers ‘lap dances and private rooms.”

Key West Scrub Club

Key West Scrub Club

Pastel colored galleries and storefronts line Duval Street in Key West

Pastel colored galleries and storefronts line Duval Street in Key West

So why am I here amidst all this craziness? A few years ago, when I was preparing to retire from real estate, I began thinking about where I’d like to live when I left the Outer Banks. I had a whole list of criteria for choosing a place. It had to be located on the ocean, be a moderate size city (not too small, not too big), have cultural amenities, have a good airport with access to International flights, have vegetarian restaurants and health-food stores, be safe, affordable, and warm year-round. The delta states of Louisiana, Mississippi and Alabama were too muggy. I’m not a Texas fan, so I scratched that off the list. For two years, I traveled to every community on the Eastern Seaboard, the Gulf Coast of Florida, and coastal Washington State, looking for my perfect place. I liked Sarasota, but eventually was lured by the tropical breezes, lush vegetation, turquoise water, and brightly painted houses of Key West.

I bought an older house in the Historic Old Town district of Key West and began restoring it. By the time I’d restored two of its three apartments, I knew this wasn’t the place for me, and so rather than move here I rented the Key West apartments to year-round residents and moved to Sarasota instead. Once in a while, however, I must come to Key West to work on the property, and that’s why I’m here at the moment. Today is day ten, and counting. So far, I’ve completed a major trimming of all the trees that were hanging over the roof or leaning on the house, the removal of scraggly bushes at the front of the house, and replaced the damaged trash bins. Later this week, my new property caretaker will do a major site cleanup.

As soon as the Key West Historic Architectural Review Committee issues my permit, the major work will begin. I’ve hired a contractor to replace some rotted siding and deck boards, power wash and paint the exterior, and install lattice skirting around the base of the house. In the midst of all this, I will be cleaning one of the apartments and interviewing prospective new tenants, since a long-time resident is moving out the end of this month. I have high hopes that the house will sell once the work is complete, because it is an excellent investment property, and when it does, I’m thinking maybe southern California. Key West is fun for a few days, but I definitely don’t want to live here. And I like Sarasota, but I’m thinking that California might be better suited to my liberal views and politics. Yep, the more I think about it, the more the west coast calls.

7 Comments on “Key West Is A Trip, And I’m Not Talking About Travel

  1. Hi. this is kind of an -unconventional- question , but have other visitors asked you how get the menu bar to look like you’ve got it? I also have a blog and am really looking to alter around the theme, however am scared to death to mess with it for fear of the search engines punishing me. I am very new to all of this …so i am just not positive exactly how to try to to it all yet. I’ll just keep working on it one day at a time.

    • Online: I use the Pixopiont plugin to generate my menu bar.

  2. I was living 7 years down there at the “end of the rainbow” – and left, befor I was going nuts myself…LOL… it was a wonderful time, but some when is the island to small and the sun burns your brain 🙂

  3. Hello I came across this site by accident, I was digging around Bing for things to do on Oahu when I came upon your blog, I must say your webpage is really intriguing I truely think the content, its amazing!. I’m in a bit of a rush at the moment to completely absorb your webpage but I have bookmarked it and also signed up for your RSS feeds. I will be back when I free up some time. Bravo for a awesome website.

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