Having gone to KW on several occasions, I can't see this as a M/C destination. Heck, I can't even see it as a beach destination as there is really only one halfway nice one. The Keys are just nasty, dirty and run down, KW is tolerable (I guess) well, more-so if you are in with the gay crowd.
U guys have fun, and don't bend over in any of the bars in KW
............At least it will be warm, so in one aspect... do it!
Every destination is what you make it I guess. Many enjoy it there and the gay thing doesn't really bother me personally in any way. There certainly are gay bars where if you/me/us go in, then maybe bending over in front of the crowd wouldn't be advised. But the main part of Duval isn't like that at all, or for that matter the other places I mentioned. The tourista dollar is king; even the big money gay owners know that. You would have to make a point of going to a gay bar AND doing the bend for it to be a problem I'd think; esp if it was closing time!
The bigger nuisance IMO are the bums. They are all over the place and constantly hitting folks up mainly at places like Duval @ night and Mallory Square @ sunset. One technique that does seem to work somewhat well is to "bum the bum". When they come over and are about to hit you up, ask 'em for a dollar, or a cigarette! It messes their thing up. I'm surprised Key West city hasn't done more about it, esp in this era of touristas.
I lived down in KW for 2 yrs way back when ('79/'80) and that was before it got so touristy with cruise ships and all. The two downtown theatres had XXX on them all the time (one theater is still there, the other marquee is part of Rexall Drugs on Duval) , and yes, there was a gay scene then - but the beauty of all this is the locals accept pretty much whatever it is you're into that doesn't hurt anyone. The summers then were the best because it was mostly locals as it wasn't a yr round destination like now. These days the real estate is so expensive no normal person can afford to live there, and even the servers they bring in live 4 to a room. Oh, and I forgot the Boat Bar and the West Key next door; one was a ***** bar, the other just a rundown local bar. The Green Parrot was a drug smuggler hangout, and today they sell T shirts and coozies....Ah, such color that place was in those days.
Beaches? That's not why folks go there; shoot you can go to beaches in New York. What fun would that be?? I do usually go mornings to the beach @ Trueman Annex USN base. Lotsa coral bits vs sand, but the water is clear and it's a nice bike ride over there. And the big lizards in the rocks are something to see! That is the real southern most point by the way, but no public access.
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The ride in and out - well, it just depends. If you go down on Friday afternoon and return on a Sunday, then it sucks usually. It seems half of Miami is headed that way! But getting down there for things like we've talked about - sunrise over the 7 mile bridge going north or south - well, it's one of the greatest things you'll ever see when conditions are right.
You are right tho, the Keys are run down in places. Kinda like, oh, NYC, Orlando, Mims, NC mountain towns, and maybe some places in your neck of the woods. Who knows, maybe some day Monroe county will tax the shabby folks out of those places and we can get pure tropical bliss from top to bottom! WooHoo!