It is not a rare thing for people to show up in Key West and transition from their boats to a life properly ashore. I did it and you might be surprised to know many elderly respectable figures in Key West did the same. For others though the lifestyle becomes permanent and it can also be unsightly as well and its a shame because sprawl on the water leads to people noticing and not liking what they see. Boca Chica Bay between Stock Island and the Navy base is supposed to become an organized mooring field which will annoy those used to living for free on their own anchors.
The city of Key West built a mooring field in the waters north of the city and charges about $300 a month as I recall which includes showers ashore, trash pick up and access to drinking water. It's really not a bad deal as long as you can handle the inconvenience of coming into town in a dinghy and living without the utility connections land dwellers are used to enjoying. I don't think of liveaboards as sailors so much as water dwellers as the vessels you see here typically don't move any more than mobile homes in trailer parks are actually mobile.
The fact is that in a town where rents are very high, rentals are scarce and wages don't cover costs, the idea of living on a boat in a warm climate makes perfect sense quite beyond the fact that a watery life is seen as romantic and piratical...The romance wears off pretty fast when faced with the practicalities but still the price is right.
I was prompted to pull over and take a few pictures from the Key Haven boat ramp after I received notice of an exhibit scheduled for the Studios of Key West I wanted to say something and encourage anyone in town to go. I intend to see it as the photographer undoubtedly has something interesting to say and there will be pictures worth seeing at The Studios.
In reading the interview I've linked to above, you will see how far away this community of people living on boats really is from the city residents in their homes. Behavior that seems obvious to me, like knocking on a boat hull, is unimaginable to the interviewer. How else do you contact the residents inside the boat? Not everyone who lives in Key West has spent time on the water.
Personally I'm glad not to be living on the water at anchor in one place holding down a day job. I found nothing glamorous about it and soon decided to sell the boat and get away from a static life in a dynamic medium. It just didn't feel right. the joy of the boat was in the movement, the change of locations, the absence of routine. To be confined to a boat stuck in one place seems the worst of all worlds.