How to capture one of the world’s most fascinating destinations in 5 hours – the seedy underside, the elegant and opulent, the quirky and bizarre, the tourists traps? And nearly everyone who works in Key West wants to put a hand in your pocket (some literally). Chickens and roosters strut freely among the tourists (like cows in India). Art galleries and pricey glass stores thrive amidst bars, trinkets and trash. Here goes, a little something for everyone.

Cruise ships disgorge tourists beside exclusive port-view hotels and Mallory Square. I arrived on a simpler vessel, the Atlanticat (see former post here).

Built in 1926, the vintage Crown Plaza La Concha Hotel is close to Mallory Square. The hotel boasts of famous guests like Ernest Hemingway and Tennessee Williams.

Typical architecture in historic Key West (Caroline St.): remnants of former gentility put to modern multi-use


The Whistle Bar in a historic building on famous Duval Street is atop The Bull Bar, and next door to The Lost Weekend Liquor Store. I lunched in a restaurant opposite named The Flying Monkey Saloon, delicious fresh fish.

The Green Parrot Bar has a webcam so if you want to see and hear the vibes going on in the Green Parrot today … so different from when Ernest Hemingway visited. This webcam doesn’t do the bar justice. When I stepped inside the bar it filled my senses with music, buzzing conversation, clinking glasses and vintage artifacts.

Writer, Ernest Hemingway’s 1931 – 1940 home (with his wife and children) is a hot tourist attraction, built 1851.

A front porch with a lot of personality
Cuban cigars make their way to stores in Key West. Of the next 4 photos, where would you want to buy an authentic Cuban cigar?

The Island Cigar Factory

Inside the Island Cigar Factory

Typical storefront for Cuban cigars

Bare-bones cigar store entrepreneur

Jimmy Buffet songs (“Here we are again in Margaritaville”) feature in his Duval St. Bar, appropriately named, Margaritaville Cafe, and claims to be the “original.”

Maybe residents, maybe passing through, but not likely tourists.

Making a living with engraved Conch shells, pronounced “konk”

The Bouncer at Coyote Ugly Saloon

Everybody’s got a gimmick. I watched Bandana Man walk with his parrot over to an unsuspecting tourist and plop the bird on the man’s shoulder. Unfortunately, Bandana Man was given the cold-shoulder by the tourist and didn’t make any money off what? the novelty? a photo? On to the next unsuspecting tourist.


World’s Smallest Bar, and there was a customer inside with probably enough room for 2 or 3 more and two more still if the stools were outside on the street.

A great band played music at the Hog’s Breath Saloon

Old cement bunker that used to house the terminal for the undersea cable that linked Key West and Cuba

Famous Mallory Square where gracious hotels in Key West’s historic port and shopping district rub shoulders with sunset buskers and t-shirt stalls. This is action central every day.

Buskers gather every evening for a sunset Buskerfest at Mallory Square. How much is instant Karma worth? $10.00

Waiting for the buskers to begin their performances. As if by magic, an array of cheap stalls lined the square with new gimmicks to part the tourist and his money.

Mallory Square companions. The shorter fellow set up a stall lickety-split. T-shirts, I believe. The friends stood by a kiosk which appeared to be a central exchange for permission tags for setting up a stall. Hawkers’ money appears to be added to a central system inside the kiosk. Baffling, but good for employment.

This fellow was a uni-cyclist and juggler. My great disappointment (when he gave permission for me to take his photo) was he blinked and I missed the reason for the photo, amazing ice-blue eyes.

A proud former Vietnam War Vet and Sword-Swallower. At least that was his story which he hyped for 20 minutes before he … hard to watch.

Colourful restaurant linked to Mallory Square.

Unusual brick architecture on Duval Street.

Shell crazy trucker-artist.

Back to gentility at the historic Cypress House Fine Lodging on Caroline St. As it was November, the hotel got a jump on Christmas with red-painted coconuts and gold sprayed branches, a few lighted reindeer … I’m from Canada, snow country. This felt bizarre, but no more so than the Xmas wreath on the front of a golf cart, or the holly pinned on a resident’s cap brim.

Never far from quirky, this Fort and Museum Bar

The bar side of the Fort and Museum Bar

And under all the hype, gimmicks and tired tourists is a tired restaurant worker taking a few quiet minutes for her dinner in the alley beside a cafe.
Copyright © 2012 by Mary E. McIntyre. Reproduction of photographs and full or partial content from Camera Combo blog only with acknowledgement attributed to author Mary E. McIntyre and the following link: http://cameracombo.wordpress.com