Truth is I usually go (or for years would be sent) without knowing what to expect. If I learned I'd be assigned there for any length of time I'd try to find whatever good things they had to offer, and MAKE it OK for myself. Did me no good to make myself deliberately miserable. I called it my "Thrive Where I'm Planted" philosophy.
But I do remember the first time I rode down the Florida Keys, in 1973. On my latest motorcycle, bought just a month earlier in Georgia. I thought the Keys were magical, and still enjoy them, although less every year as they continue to be degraded by continued commercial development.
In '73 things were a lot less crowded, less overbuilt, and much lusher with the kind of heavy vegetation you might associate with the tropics. With more swampy mangroves than today, and oddly fewer palm trees, which I believe aren't really native. But were originally introduced there by people. Key West was a little gem at the end of your 100-mile trip.
Already a bit shabby, in a quaint, quirky & colorful way I came to love. With delightfully eccentric residents who seemed suited to their exotic surroundings, many living as though they imagined themselves to be perpetual beachcombers.
And all through the Keys I always had the sense that I was really in the middle of the ocean, easier to appreciate when you travel by motorcycle. Even more so when you travel that route pedaling on a bicycle, which I've also done a few times.
Because the Keys actually are fairly small islands far out from the mainland US, an archipelago situated between the Atlantic and the Gulf. With only bridges connecting them to make a trip by vehicle possible. One of these many structures, the aptly named "7-Mile Bridge" has to be that long to span the water at one point.
Since the mid-1990s big cruise ships have been making port calls in Key West. The thousands of tourists flood through historic Old Town like a tsunami, then retreat like the tide going out as their ship readies to continue on its way. Large hotels have been built along the water, grabbing much of the limited beaches for themselves, and blocking the views.
Land prices have skyrocketed, and the locals are becoming extinct, notably the once-numerous gay community. What had been charming has become contrived.
And increasingly like living in a rather self-conscious theme park, complete with open-air tourist trams riding the streets, blaring their tour guide's descriptions over loudspeakers. Hard to find anything genuine anymore, that's not deliberately put there to catch the tourists' eye, as well as their money.
And so for me, Key West represents a bit of both this thread's conditions: once had been better than I had imagined, an amazing revelation, and today becoming more of a disappointment. I still go, perhaps seeing it through the nostaslgic lens of over 40 years ago. And knowing where the "real" Key West remains, away from the show made for the stampeding day visitors.