crazy little village ... southern most point of the united states
full of crazy and homosexual people, usually drunk or high
party town
"this town is a crazy party town"
"it's like Key West then"
by crazymofous July 11, 2008
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Coming from someone who lives here, this is quite possibly the biggest shit hole in the world. Everybody talks about how it's paradise but thats becuase they're only seeing this town from a tourist point of veiw. Also, the only places to hang out are the movie theaters, which have the rudest people working there, and the skate park. Thats it, there are no other places for teens in key west to hang out. Everywhere else you go is full of drunk people. Also, the school system here is pretty bad, the schools have almost no funding and the teachers couldn't give to fucks wether or not we get an education. Also, since this town is so freaking small everyone and I mean EVERYONE knows your buisness. This town is FULL of gossip and I freaking hate it.
Person 1: So you live in Key west huh? Lucky, I wish I could live there.

Person 2: No, you don' me.
by Little_miss_awkward February 5, 2012
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a city in Florida in monroe county, florida

natives are referred to as conchs.
lets go to the southern most point city which is Key WEst.
by kilas May 1, 2008
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That guy walks like he has been Key Wested.
That girl walks like she has been doing a lot of Key Westing.
by Swisscnc June 9, 2006
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Aka: Goatee; A pattern of facial hair on a homosexual male, forming a circular targetoid shape around the mouth. Origin in key west in the late 80's.
Mahal: Hey greg, you know sandy and her cousin kenny?

Greg: She has a lot of cousins- which one is he?

Mahal: He's that 40 year old dude with the old used corvette and a key west bullseye.

Greg: Oh yeah- that guy- I know exactly who you are talking about.
by schmuckaneers June 4, 2009
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When a man inserts the end of his penis into his own asshole.
That dude is so gay that he gave himself a Key West Boomerang just to get a piece of ass.
by Mr. Clit June 6, 2006
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A sexual maneuver popular in island communities populated by chain-smoking men with tiny penises, the recipient is mounted and subsequently fucked in their tracheostomy hole-- typically with enough force and velocity to cause the expulsion of dentures as the erect penis continues on its path out of the oral cavity.

Occasionally, after long sessions repeatedly entering the tracheostomy stoma and exiting the recipient's mouth, the penis can become entrapped, as the engorged head of the penis is unable to retract beyond the recipient's gumline. This condition is known as a Reverse Columbian Necktie.
"Tyler was humiliated and laughed at by his recently-crippled girlfriend and her nurses because his small penis couldn't penetrate during attempts at vaginal sex, and someone posted a video of him falling off her when his penis popped out while attempting a Columbus Side Car.

Swearing off women forever, Tyler decided that he would immediately break up with Jessica, quit his job, and move to Key West that very night.

Jessica started on him as soon as Tyler walked into her room to tell her goodbye, but he didn't care. As a parting gift, Tyler gave Jessica a Key West Necktie, walked out, and since he had a few hours before his flight, proceeded to have a few beers celebrating the first--and last--time he was able to leave a woman speechless.”
by Scoggy July 19, 2019
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