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To tell you the truth, I don't really remember all that much about Key West. It was our first port of call on our first cruise. We were totally unprepared. I remember wandering around, pissing off a hostess at Jimmy Buffetts Margaritaville restaurant by asking what time they opened, eating an awesome piece of Key Lime pie and going back to the ship.
Oh I know what else.
We went into town on a bus and listened to the driver drone our his tired old speach that he had obviously done a zillion times. Only the doltiest dolts of the bunch laughed at his jokes. This was not written by Hemmingway, one of the area's claim to fame, the other being Harry Truman. Well guess what? Harry lived just a few miles from our home here in the midwest and I never thought all that much of him either.
Which reminds me!
Lately I have read reports that the natives of Key West are having some problems with "all the cruise ships" that are docking there. Yeah right. Shut it up Key West. All those shops seemed quite happy to take all our dang cruise ship money I'll tell you that for sure.
I think I remember more about Key West than I thought I did
I recall thinking at the time that the people were kind of cold. Now, many cruises and ports later I think I have to agree with my original take on that. Maybe the whole town was having a bad day but they were not nice. As Lisa said "they were cold to the point of being rude" "I liked the town but the people were just plain rude" A far cry from the nice people in Miami.
UPDATE: Fast forward 5 years. Key West got cleaned up and friendly, go figure.

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