I lived in the keys for two winters. Working and living in Key West is definitely different than just visiting, but either way it has its merits and its faults. On the good side: Lots of characters, laid-back aura, great seafood, fun nightlife. Bad side: Too many tourists on one street, shops are overpriced and pedal crap (mostly T-shirts), locals can get kind of flippant with outsiders. Some of the best and worst: Sunsets on the pier, Sloppy Joes, the Green Parrot, Rick's (ugh!), Duval in general, Half Shell, Pepe's, Blue Heaven, cigars everywhere, rum everywhere, Hemingway....All that said, I met some great people, gots lots of sunshine and had an excellent time. It's a treasure to behold. And the livin is definitely easy....
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