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Key West, FL

If you go down to Key West in the off season, aka when it’s roasting hot (August into October), you’ll enjoy a lot more of Key West’s appeal – it’s a spooky place.  I’d expected Key West to be sort of a retirement-home- with-spring-break-perpetual-foam-party, with old men leering and keggers on every corner, which wasn’t what I was looking for, but snorkeling had been dangled in front of my face, so I went on. The city sells souveniers referring to it’s wish to become “The Conch Republic,” and after a few days there, you soon see its foils of the party-image of Florida. Here are the exhibits – would the jury please note that relaxing, of course is priority one when in Key West, but having fun is often a very close second.

Exhibit A: an imposing Presidential home (only used by Truman – ah, those Cold War days of yore) that is still arm-guarded and rather menacing from in contrast with the beautiful old architecture (like that around the tourist-laden area near the Custom House) and laid-back attitude of Key West. Also, the majority of Key Westerners are either independently wealthy or working about three jobs to afford to live there – there’s a hustling spirit (check out the Prohbition-era carvings in the gates – the ones that look more like beer bottles than roses means you could drink there) that bumps nicely against the beach vibe.
Exhibit B: Ramshackle tin-roofed open-space areas are the best, bar none, spots to grab food. Look out at the ocean – that’s where your food came from. This morning. Skip Jimmy Buffett’s “Margaritaville,” but do buy a key lime pie from the Blonde Giraffe – the local pick for the best pie.
Exhibit C: Aside from, say, Miami, Key West has arguably has Florida’s drag queen population on lock; expect to have fabulous conversations with men who know how to draw on eyeliner with enviable precision.
Exhibit D: Spectacular snorkeling. Take the catamaran. It’s awesome.
Exhibit E, for Earnest: When you’re in his cavernous, sprawling home, only seconds away from the bars, the lighthouse, Mile Marker 0, and the place where you are really close to Cuba (the southernmost point of the US, according to the monument everyone takes a picture of – so did I), you can really feel Hemmingway’s good side. He was a rascal, a jerk, a genius, an idiot, and a clever bastard, and the tours of his home are entertaining as all get out – and yes, you can pet the cats. Fun trivia: Hemmingway’s home has the only basement of all the homes of Key West. Take a tip from Earnest and just wander the city, feeling that Tennessee Williams’-style (he wrote a few plays when he lived there) edgy heat that gets you loose and laughing.

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