It's behind Turtle Kraals, the dinghy dock that serves the anchor-outs living on the hook off Fleming Key and around Christmas Tree Island (named for the Australian pines that flourished there), known to chart makers as Wisteria Island (named for a ship that foundered there years ago).
The one big issue that faces people who travel on boats is where to park their dinghies when they put down their anchors and want to go ashore. For those with money one of the attractions of stopping off in marinas is the ability to tie up to the dock and simply step off the boat. For those who don't want to spend, typically between $30 and $100 a night (for a typical 30-40 foot liveaboard boat), but a night at anchor is splendid. It's self sufficient, it's got more privacy, better scenery and it's FREE! Then there is the problem of how to get ashore if you want to go shopping or see the town or buy spare parts.
Things are always breaking on cruising boats and finding parts is a constant issue. So it is that towns that have boating populations frequently offer dinghy docks. Key West has two official such docks, one at Garrison Bight and this one, more downtown behind Turtle Kraals restaurant and bar ($6 a night or $80 a month, no dinghies over 12 feet in length, trash, showers and water included).
I wander along the waterfront from time to time and I watch the comings and goings of the water rats, many of them youngsters, some of them retirees and a very few in between, and I can't say I envy them, though I remember my previous life fondly.
I still have opinions about which dinghies make the best vehicles to get ashore, and they fall into two main camps. The inflatable dinghy made of hypalon or some such material:
Difficult to tip, easier to stow sometimes, surprisingly tough, though difficult to row. Or there is the hard dinghy camp which I think frequently ends up being the choice of the boater who lives firmly in one spot and rarely moves the "mother ship." Not generally what I call a "sailor" but more of a a liveaboard:
One of the observations I have made over many years of living aboard and cruising is that a person's mobility is in inverse proportion to the size of the dinghy. If you see a small sailboat with a large well equipped hard dinghy hanging off the stern you can bet they haven't pulled up the anchor in a long while. There is a form of snobbery among boaters about these things and people are always being judgemental about each other in the way humans tend to be. My wife and I belonged in the inflatable dinghy camp and on our Gemini catamaran we had what we considered an excellent solution for transporting our dinghy:
Some sailors think hanging the dinghy off the back of the boat in davits is dangerous at sea, but like I said everyone in the world of boating is a critic. This picture was taken while cruising the north coast of Cuba and we had hauled the dinghy from Santa Cruz California, off the back of our Gemini 105 without a problem. Some people with large boats have large dinghies. I remember being anchored in San Juan Del Sur in Nicaragua when a very large "gin palace" was visiting the town and we felt like peasants when the crew of the big motor boat stepped off a dinghy two thirds the size of our 34 foot (11 meter) catamaran. They had a steering console on their dinghy, but that's a rare feature for we the little people. I found on at the dinghy dock on a regular sized dinghy:
Living on a boat at anchor appears glamorous to land lubbers a lot of the time, but when you look closer it takes effort and energy and organization to do it well. You don't want to forget anything on your shopping list because in that case you do without.
And you may be anchored half an hour from the dinghy dock across cold choppy waters...On an afternoon when skies are gray and the temperature has dropped to 70 degrees (20C) you might miss the comfort of a commute by car:
And while we are pointing out the most romantic parts of living at anchor let's not forget "dinghy
butt" which is the experience of getting your backside soaked while traveling to or from your boat. Going to the boat isn't so bad as you have (I hope) clean dry clothes on board. All you have to do is strip, rinse and hang your underwear on the lifelines right between you and the sunset you wanted to admire. Coming to town "dinghy butt" is a whole other world of hurt. Imagine walking all day, shopping, going to the movies, sitting on a bar stool, or even standing at work for eight hours, with a salt water rotted crotch. Yes, you can pump out your dinghy all you want but that one small, mild mannered wavelet will leap up three minutes from safety and dump salt water all across your nether regions.
Then there is the problem of dinghy motors. Hardly anyone rows any more, and even though some still do almost all anchor outs rely on small, two and increasingly, four stroke motors. Which don't always start when they haven't been cared for properly:
See, there I go being critical. Actually she sounded a little miffed too when she hissed: "Just get it started!" he was commendably restrained just pulling the rope in silence until finally he was rewarded with a grudging, choking cough. I'll tell you what though, if he doesn't get it sorted and reliable he will be single handing soon enough. This guy appeared to be single handing already and he was working on a recalcitrant old British Seagull, the original two stroke outboard motor developed in World War Two. And notoriously unreliable:
Actually they are very dependable if serviced regularly and treated with the care a small engine deserves in a harsh environment. If they won't start they are horrid, as the starter rope has to be wound round the flywheel for each try:
He too suffered in silence, pulling away and guiding his dinghy with his paddle between pulls:
He was smart, though, or experienced because he carried alternative propulsion with him, even it was just a paddle. A dead motor is crippling especially in Key West harbor waters which have fierce currents and lots of assorted traffic. Eventually he buzzed off as can be seen further up this essay. There are rules about what you have to carry including lights, fixed in this case though an all-round white flashlight will do if your dinghy is slow, less than seven miles per hour (12km/h):
You need life jackets and flares to be legal and registration if your boat has a motor in Florida. And if you don't you can expect to get stopped by the Marine Patrol, known these days as Florida Fish and Wildlife and get fined if you aren't in compliance. Occasionally Key West PD gets in on the act too, and because Key West is, effectively, a border town the feds are here in force, every letter of the alphabet soup, DEA, FBI, JIATF, and no doubt CIA though I'm sure they couldn't care less if your dinghy has lights or valid registration. Naturally anchor outs fancy themselves rebels so they make a point, many of them ,of flouting this or that. I always preferred to fly under the radar and not draw attention to myself. Which is why I still have factory mufflers on my motorcycle. I am a milquetoast rebel.
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Once you get used to the idea that many working people live on boats you can get to recognize them by certain signs they give off. Live aboard boats need electricity so some have wind generators like this:
Others have solar panels like this, in Gun Cay, Bahamas, though they work fine in a marina too:
Bicycles work well for people who live at or near the docks and boaters tend to prefer small wheeled fold up bicycles thinking they are easier to carry in the dinghy:
Which they are but they are never easy to get back on the boat. Plus they are cumbersome to store in most boats and end up living on deck and rotting away...that's my opinion and I'm sticking to it! Liveaboards are identifiable too, certain clothing choices, a certain swagger perhaps because they think they live a cool "lifestyle" which I suppose they do:
"Be safe!" she called out as though the dinghy ride to the boat is less safe than a roadway commute, a touch of the high seas adventure for people who's boating tends to be limited to the harbor waters. That became the problem for me. Living on the boat and working a job turned the boat into a parked vehicle, too cluttered to sail, too tired to clean up and take off. Now I live in my house I go out on my little boat far more than I ever did when I lived aboard, even in a marina, and held down a job. For youngsters and would-be adventurers the big back pack, the small boat and the envious stares of the land lubbers make it all worthwhile:
For those seeking photographs and commentary on the life truly cruising I recommend the
Log Of Whisper in my blog list, a Caribbean cruise sadly drawing to a close, recorded by a young couple with lots of pictures and stories to tell of the high side of getting out there and breaking loose the anchor. The best reason, in this opinionated land lubber's mind, for bothering to deal with dinghy butt.
Simonton Beach was the place to go when a Spring cold front blew through town. Winds were honking out of the north and temperatures were down below 70 degrees (19C). I like to go to this tiny pocket beach at the north end of Simonton Street when the weather turns rough. It's a narrow window on the Key West harbor and you get a taste of nature's fury, though only a tiny taste:
It takes a hurricane to get really big visible waves but it was rough out there to a degree and I was glad to be on the beach. Usually there are a bunch of bums - for want of a better word- hanging on the beach but there weren't that many this cool afternoon, including a wannabe band member:
And a very busy dog:
The beach is also home to anglers, including this one happily dangling bait and catching nothing. He was an Englishman, possibly on vacation having a good time in the breeze:
At eleven at night everyone is supposed to go home:
People come by car or scooter for a quick look:
Some show up by bicycle, others on foot:
Some of the visitors come by stroller too; they get an early start on learning to enjoy Key West:
And quite a few of the visitors don't show up at all in person; they just like to watch, as it were:
Simonton Beach is something of a canyon wedged between tall hotels, the Hyatt to the north...
...and the Pier House, Key West's original waterfront development to the south:
And between them one gets a sliver of a view of the harbor waters, here with Sunset Key in the distance:
And here with the military base on Fleming Key jutting up to the north on the right of the picture and a tree covered spit of Christmas Tree island to the left:
Simonton Beach is a functioning launch ramp, though this four wheel drive truck spun his front wheels as he clawed his way back up through the deep sand...
...while the jet ski took off for the horizon to the west aiming at the area of shallow waters and mangrove islands known as The Lakes:
Some of those people living on their boats at anchor use the beach as a place to leave their dinghies.The good news is that it's free to leave your dinghy here but the bad news is it's wide open to any passer by. Thus it is most people leave less desirable hard dinghies here, that are also easier to lock up to a piling:
It would take dedication to decide to go kayaking in a cool north wind blowing 25 and gusting 30, but if you are young enough no water is too cold to paddle in:
And me? I had a date for fish at Alonzo's with my wife, and I managed to take enough pictures at that place for an essay about the Galleon Marina which will appear here in the fullness of time.
So it was south one block on Simonton, north one block on Front as odd as that sounds, and into the free motorcycle parking lot followed by a short stroll on the boardwalk to a Yuengling and clams and fish fingers and shrimp. I left the people to freeze on the beach.
The bridge used to provide land access to an almost uninhabited island on the south side of the city of Marathon. This is how it used to look as it started to open to allow a sailboat to get into Boot Key Harbor from the west (and these docks in the foreground are due for restoration as part of the new Faro Blanco resort that is in the works): 
Nowadays the only way to get to Boot key is by water and the reason is that old bugaboo: maintenance. The bridge was too far gone and no one wanted to pick up the tab for repairs, most likely several million dollars worth.
The state said no thanks, this road is a side show and serves no useful purpose. The city of Marathon joined with the county in saying no thanks, but unlike the state and the county the city was in a slightly more sticky position. Land owners want compensation for being cut off from their formerly uninteresting mangrove lots.
The bridge is squarely in the city of Marathon's jurisdiction and even though no one lives on Boot Key several people own parcels on the island and there is also an AM radio station that broadcasts from amidst the mangroves. You can see the antenna rising above the greenery:
The radio station owner got predictably incensed and the employees found themselves getting ferried to their jobs across the water. Hopefully they enjoyed the novelty, but by now months later the novelty must have worn off. I haven't heard what the latest plans are, if any, though no doubt lawyers are hard at work out of public sight. The bridge itself makes a convenient dinghy landing for liveaboard boaters in the channel:
The island itself I visited a few years ago, fed as I am by my insatiable curiosity. All I remember was a long straight road with a sharp bend at one point. It was smoothly paved and lined by the usual mangroves and discarded trash.I saw no reason to return, except now I have a place for photographs that I never took at the time. Never mind, the view west down the channel is charming:
And the view to the east kept these two codgers entranced as they shared beer and cigarettes and traded horror stories about the iniquity of prices at Winn Dixie:
I listened as I took pictures, and bid them a polite good day as I turned back the way I had come, down 20th Street, which stretched to the horizon, or more accurately to Highway One:
And there was my Bonneville on the proper side of the barricades:
Ready for a quick getaway from this sad and desolate place. 
I have previously mentioned that in years past the city commission pondered the requests of neighbors asking that the southernmost point be moved to relieve them of the constant press of tourists. Geography is a flexible concept in the southernmost city, but for the moment the point continues to reside at the corner of South and Whitehead Streets. This is a small slice of Whitehead at 2:30am.
I find that photographing the most mundane thing in Key West at some ungodly hour of the night has the capacity to make everything appear far more exotic. The picture above resembles somewhere far away in my mind's eye, the Morocco perhaps of my youth, and it's just a scooter on Whitehead. 
For the price of a drink the guest house allowed locals to sit by the pool at the magnificent pile, but after the city commission denied them a permit to expand their operation the family sniffed in great vexation, swept up their toys and decided that no more would they allow hoi polloi by the pool. The stand off continues, and if you think petty nonsense has no place in paradise you'd be dead wrong. Either that or Key West isn't really paradise which is a thought no serious tourism agency would countenance. There is another fine structure across the street , the southernmost something else that I can't remember:
And if you park your Triumph Bonneville in the middle of Duval Street between these two structures and point your gorillapod-mounted camera due north this is what you see:
Duval Street sans people. Just how I like it.
The city's administrative offices on Angela Street got Wilma'd in 2005 and they have been rather unpleasant and moldy ever since. So the city is looking around and considering building new offices somewhere. Which is a pricey proposition at a time when even our leaders have noticed a bit of a problem with the economy. They had thought about buying the Gato Building on Simonton Street from the County for a nominal sum, but calmer heads prevailed and a more ambitious building plan is still under consideration at far greater public expense. The Gato Building named for it's 19th century builder, was created as a cigar factory, and it has a rather more refined air than one might expect for administrative offices:
The fact that it has parking attached and actually looks like a dignified setting for a municipal nerve center probably constitutes a second strike against it ever becoming Key West's offices. Across the street there is more open space available. A 1200 square foot (110 square meter) junque yard:
Pitch a tent and there you are, another variation on the not-quite-affordable housing problem in the city. I was running out of time, as seems to always be the case with my meandering lunch breaks, yet there was time enough left for the cup that refreshes:.jpg)
A cafe con leche, known to some sceptics as a "liquid candy bar" but they are bitter people who like their coffee bitter too. A little sweetener, a moment to sit and think of nothing at all at White Street's 24 hour cafe, Sandy's, the other landmark: .jpg)
And from there back to work, for a few more hours till dawn.