Aside from the regular tourist spots, there’s so much more to Key West than meets the eye. You just have to look for it.
Each trip, I always make sure to get up before sunrise at least one day and take a hike around old town to discover more beautiful things the city that we love. The majority of the images in this post come from my early-morning travels. We’re heading back down in April for a few days and I totally expect to be meandering around the back streets just after sunrise. If you’re a Key West resident and you see a guy walking around with a camera and a green backpack slung over one shoulder, be sure to stop me and say hi. A cup of coffee would be nice, too.
Everyone should know this landmark by now. Installed in 1983, it designates the southernmost point in the continental United States. Actually, it’s the southernmost “public” point. The real southernmost point is on the naval base west of here. I can remember when the only thing here was a rusted chain link fence with a small, white sign that read “90 miles to Cuba” with an arrow pointing off into the distance. There also used to be a semicircular, wrought iron design at the end of the current fence. Not sure what happened to it.
The buoy usually has a line of tourists all waiting their turn to get a picture taken in front of the monument. Even getting there as early as I did, I had to wait until one family took their fill of pictures.
Sails off of Mallory Square shortly before sunset.
Not everything is pretty in Key West. This house on Elizabeth and Fleming is in desperate need of repair, as are others around Old Town. The empty wine bottle is indicative of the drinking problem that many of the homeless there face. I’ve desaturated and darkened the sky in this image to emphasize that not all skies are bright and blue.
In 2007, the Just 4 Kids charitable organization was asked by the Florida Keys Aqueduct Authority to paint roughly 300 Monroe County fire hydrants. In this one example, we see an artist’s rendition of the Southernmost Point buoy. I’ve seen a quiet a number of the painted hydrants around town and they are well executed. Each hydrant is both designed and painted by the kids.
The Stop –n- Shop food Market at the corner of Whitehead and Virginia, it’s proprietor cleaning up and getting ready for another day.
The Artist House on Eaton between Simonton and Bahama. This was once the residence of Robert, a supposedly haunted doll. He’s actually quite big, standing three feet tall. Robert is sometimes referred to as the original Chucky. Enter “Robert the doll” into Google or Yahoo and see what comes up. The house is a favorite stop along the Key West Ghost Tour and is sometimes seen in television documentaries on the supernatural. It was built between 1890 and 1898.
We’re staying here in April… in Robert’s room.
Here’s a picture I took with Robert about 10 or so years ago (that’s my arm in the lower right). He’s kind of creepy.
Someone has painted something they believe in on the side of a building.
Kermit’s Key Lime Shoppe on the corner of Greene and Elizabeth. Probably the best key lime pie you’ll eat. Don’t forget the key lime cookies or the key lime fudge. All home made. I think my favorite is a frozen, chocolate covered slice of key lime pie on a stick. Nothing beats it.
This looks to be part of the Just 4 Kids project, but I can’t confirm. The signature reads Maria Candelario. Chickens have always played a big role in Key West. There are a couple thousand free range chickens roaming the island and the residents are divided about whether or not they should stay. Quite frankly, I can’t imagine Key West without the chickens.
I saw this funky parrot on someone’s bike outside the old Customs House, now the Key West Museum of Art and History.
A curious tourist peeks inside the Key West Shipwreck Historeum and Museum on Whitehead and Wall.
Starfish. Lots of starfish.
Cigars. Lots of cigars. Key West was once known for its tobacco industry and cigar shops are plentiful.
Birds take flight shortly before sunset. 
Even the police department gets into the spirit. “Protecting & Serving Paradise”
One of the many performers at Sunset Celebration at Mallory Square. A tourist looks on as this One Man Band performs for the crowd for tips alone.
I’d like to think he’s doing this for some extra cash, but his face might tell a different story.
Just off Mallory Square is El Meson de Pepe, one of our favorite restaurants. The atmosphere is always great, whether you choose to dine in out. Inside, enjoy the live music, artwork, and memorabilia. Outside, enjoy the fresh air, live music, and the chickens in the trees.
I’m not sure just how many bars are in Key West, but walk up and down Duval and you can’t help but fall into one, or two.. or three.
Dormers. Location unknown. Probably somewhere along Eaton.
Many houses still retain the beautiful scrollwork and gingerbreads.
A nice touch on an Old Town fence that is duplicated on the door behind it.
Captain Tony’s Saloon. This was the original site of Sloppy Joes until it moved across Duval in 1937. Hemmingway said he spent so much time in front of a specific urinal here, that when Sloppy Joes moved, he took the urinal and transplanted it into his garden. It is now part of a fountain that the many polydactyl cats on the property drink from.
These folks are obviously pro-chicken.
Renting a bicycle is a great way to see Key West. The island is only 2 x 4.5 square miles so getting around by bike is quick and efficient. Come to think of it, walking doesn’t take too long either, especially if you’re sticking to Old Town.
B.O.’s Fish Wagon on the corner of William and Caroline.
The sign reads: “B.O.’s reserves the right to close early, open late, or remain closed any day for any reason. This includes, but is not limited to, bad weather, beautiful weather, bad fishing days, good fishing days, exhaustion, hangovers, or a good party. We do not recommend this establishment if you are in a hurry, sensitive, or accident prone. No Sniveling Please.”
Only in Key West…
A number of homes in Old Town are in need of care. Some are just simply falling apart. This is what happens when a house well over 100 years old has no one to take care of it. Still, you need to be fairly wealthy to purchase a house like this. One such place across from the Donkey Milk House on Eaton is currently going for $4,750,000. Yes, that’s $4.75 million. Reduced down from $5 Million. Times are hard.
A wonderful touch for an Old town home. I also love the conch door stop.
I’m not sure of the history of this house, but its owners seem to like lions – they decorate the exterior of the house.
Universal Cleaners on Elizabeth between Fleming and Southard. It’s kind of a minor landmark because of the sign. I’ve seen a number of people hitting my blog searching for “gentle cleaning key west” or some derivation of that. Sadly, Universal Cleaners has gone out of business. The inside has been gutted and the building is for sale. I do not know the history behind the sign or the building, but I’m going to try calling the owner to see if I can find anything out.
And this is something that you won’t see anywhere else. If you’re casually walking down the street, you’ll miss it for sure. Seems that the sign’s design, and possibly the business itself, was inspired by the owner’s cat, Jackie. Very touching.
The La Concha Hotel, previously known as the Hotel La Concha. It first opened its doors in 1926.
More dormers. Plenty of these in Old Town. 
A Volkswagen Thing with Ohio plates. KW THING.
