Key West, Florida. Land of Jimmy Buffett music, beaches, booze and bikinis. (Also bums, there was a LOT of them!) I have had the fortune to have been there twice and would like to offer you my observations of each time. Today I’ll tell you about trip #1.
My first trip to Key West was rather unusual. Back in 1996, my brother in law had been talking about going there forever but as he was a single guy didn’t have the guts to go by himself for some reason. So my wife suggests that I go with him. Who am I to argue with that? So off to Florida we go! This will be interesting as I am married and outgoing and he is single and an introvert, who doesn’t drink. To start with you have to fly into Miami most of the time. Then you have a rather long drive thru the swamp and then across the various keys until you get to the very end, key West. So we rented a car (a Mustang convertible) and off we go.We head south (of course) and enter the Everglades. The road is literally carves out thru what appears to be the middle of the swamp. You certainly don’t want to go off the road here or you might get eaten. So here we are, driving along around 70 MPH, top down, music blaring, what little hair we have left blowing in the breeze, when we see what appears to be logs by the side of the road ahead. As we get closer, we realize that they are not logs, but 2 alligators (or crocs, I don’t know the difference). Then all of a sudden one of the gators darts of into the road. I’m thinking either we gonna get us some boots or we are going to hit that thing and go launching into the air. Somehow brother in law managed to avoid both of them without killing us or landing us in the swamp. Needless to say he slowed down the rest of the way thru the swamp.
The first Key you hit is Key largo, of musical fame thanks to Bertie Higgins. You know you’ve heard the song, if you are older than 30. My first impressions back then was that this place was most certainly not ‘paradise’. It looked run down, faded and like a broken town. traffic was pretty heavy on the main road but none of the businesses seemed to be thriving. Don’t have much other impressions on Largo as we just kept on moving.
After Largo you pass over many small bridges connecting the islands together. Some of these are maybe a mile long, some not even that. After several of these you come to the next major Key called Marathon. Marathon was a little busier and looked a bit more lively than Largo. It even has a small airport for puddle jumpers. We stopped here at some seaside dive to get some food and gas up the car. Tons of seafood (of course) which I don’t like so I just get a hamburger. Food was good and the people seemed nice. Our impression was that this key was a lot more happy than Largo was. Back in the car an on we went.
Just past Marathon was the longest bridge span on the route. You drive for miles and see nothing but water. If you have a fear of bridges or water, do not ever make this drive. After that you hit the more Keys, Big Pine, Summerland and Cudjoe. One thing that seems to be very common with all the keys is that every one of them, even all the small ones, has a bar/restaurant right where the bridge connects to the island. They all look rundown and have at least one or two boats by them, but none look inviting to the casual driver. So of COURSE we stop at one to get a beer. Our first impressions were not far off. We talked to the bartender/owner and the place doubled as his house and he just sells stuff to the occasional tourist to keep himself busy. One of the boats outside was his and he just closes when he feels like going out fishing. I finished my beer (BIL had a coke) and we left. Almost there!
A few more islands and past the naval air station and we finally arrive at Key West! We ended up in a pretty crappy hotel about as far from the bar scene as you can get and still be on Key West. It was about 4 in the afternoon so we just put our stuff away and went to town to explore Key West! The bulk of the bars and stuff are on Duvall Street. The street is about a mile long and has everything on it a tourist trap should. We ended up at Margaritaville, of all places, and had an average burger and a few beers. People are everywhere, and of all shapes, sizes and colors. A virtual cornucopia of people! Most seem to be having fun and just about everyone has a drink in their hand.
We spent 3 days there and the general observations were that this was about as touristy as you can get. There is an area where they allow street performers and it was just loaded with grifters. I even saw a pickpocket attempt who got caught, so I REALLY paid attention to my own stuff. There were lots of bums, several ladies I was sure were hookers and booze everywhere. Food was average at best unless you got seafood. Beer was expensive! For the most part it was uneventful but we had two nights that were interesting.
The second night we were there we ended up at a bar that had a one man band playing who was pretty good. We grabbed seats at the bar while we drank and enjoyed the music. After an hour or so a young lady sat down at the bar next to me. We started chatting and I introduced myself and my BIL. All three of us talked for at least an hour or so as we enjoyed the show. BIL is actually talking to a girl (!) so I decide that I am going to excuse myself to use the restroom and see if he makes a move. So I grab my beer and just take my time wandering around the entire bar. 20 minutes later I come back, there is still an empty seat between them. WTF? So I sit down and we listen talk and drink some more. BIL is again doing a lot of the talking with her so another hour later I again excuse myself to give him one more chance. 20 minutes later I return to the same stalemate, my empty chair between them. It is approaching closing time so I don’t think this is going to happen. The performer says thanks and ends his night and the bar announces last call. As we get up from our seats, the girl looks at me and says “I was wondering if you would like to walk me back to my hotel? ” I just stand there not saying anything because I wasn’t sure if I heard that correctly but then she puts her hand on my chest and repeats the request. Why didn’t this crap happen to me when I was single? I take her hand and tell her thanks, but perhaps she missed the part where I said the other guy was my brother IN LAW. Or perhaps she missed the wedding ring on my hand. Or perhaps she didn’t care? Regardless, we all went home alone.
The last night there was just a bit weird but no girls hitting on me. We were in one of the bars that had multiple floors. We stayed on the main floor for a while because they had a band that was pretty good. BIL was even drinking a bit. After an hour or so we went up a floor. There we were able to snag seats on the balcony overlooking the street allowing us to people-watch as we drank. We ordered some food and BIl was getting a little tipsy as he doesn’t drink often. It was still early, maybe 6 PM so it was till very light outside. We watch the people for maybe an hour and decide to check out the top floor, which was really a rooftop bar. As we get out of the elevator there was a sign that I didn’t really make out clearly other than the word ‘optional’. Once we stepped out onto the roof, I figured out just what that meant. Clothing optional. We sit at the bar and a huge boobed bartender comes over and takes our order. A minute later she saunters back with two cold beers and she lingers around for a moment, knowing that we are savoring the view. The area behind the bar is a bit higher than normal so we get to see everything. She wanders off to attend to another customer so we grab our beers and turn around to survey the scene. There are maybe 20 people up here at this time, half are clothed like us and the other half are about even split between guys and girls and run the gamut from topless to full nudity. I drink my beer pretty fast and turn around to order another one when my big-boobed bartender was replaced by Joe the leather-biker dude. Here before me was this hulk of a guy wearing an outfit that consisted of a few leather straps all connected to a cock ring around his rather large man-meat, which I noticed was sporting a piercing on the end. I did not need to see all that. I can’t UNSEE all that. He asks if he can help me so I order my beer (dammit, I’m thirsty!) and just leave my money on the bar as I turn around to hopefully see something else. All this time my BIL has been looking into the crowd so he hasn’t seen that yet. The guy comes back with my beer and says ‘here ya go’, and with that my BIL turned around. He was smiling when he did, perhaps hoping to see some breasts, but instead he got a clear view of the pierced manhood. He just gets up and heads for the elevator. I look back to the bartender and just shrug my shoulders, leave a tip on the bar (no pun intended) and off we go.
So, my first trip to the paradise of key West can be summed up as this: Super touristy, expensive party town. Which is good, if that’s what you are looking for. Oh, and the sunsets and sunrises are spectacular over the water. Trip #2 next time.