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Quaint And Quirky Key West: Margaritaville And More

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A sign at Mallory Square in Key West, Florida, says it all:

“Where the sun sets and the fun begins.”

For years, Key West, Florida intrigued me.

Already a long-time fan of west coast Florida, where I had spent many winter vacations with my parents at their beachfront timeshare, I yearned to travel even further south, to the southernmost tip of the Sunshine State – and the continental United States.

I have a personal interest in this city, best known for Jimmy Buffett and his famous “Margaritaville”, that dates back to 1924 – the year my paternal grandparents were married – at the county courthouse in Key West.  How my grandparents came to be wed in this beautiful tropical paradise is a whole other story in itself.

And so it was with great excitement last November when we got to spend a day (which, frankly, isn’t long enough!) in quaint and quirky Key West.

I had been given all kinds of advice from my sister and brother-in-law who have visited there, and my cousins who spend their winters in a nearby Key, but nothing prepared me for the sights we would see in Key West, Florida.

Around every corner, down every street, from every point overlooking the ocean, there was another sight to behold. There truly isn’t another place like Key West, Florida. You have to see it to believe it.

So until you have the chance to visit Key West and the Florida Keys for yourself, slip into your most comfortable walking shoes (because you really can walk from one end of town to the other!), and follow our one day journey around quaint and quirky Key West!


Houses like this one line the streets of Key West. It’s these “southern Americana” homes that make Key West so quaint. With their painted siding, balconies, American flags, and lush vegetation, Key West houses like this show such pride of ownership!

Key West Houses

I’m not one to usually take photos of houses while on vacation, however, some houses were so picturesque, I couldn’t resist!


Upon arriving in Key West, we stepped back in time when we paid a visit to Ernest Hemingway Home & Museum. Ernest Hemingway called Key West his home for over ten years, writing some of his most famous novels here. It was at Hemingway Home & Museum where we had our first encounter with one of the more unusual sights in Key West – six-toed (polydactyl) cats! All the cats at the home are descendants of Ernest’s original six-toed cats!


It was during our 90-minute tour of Key West with Old Town Trolley Tours, which takes you around the entire city of Key West, that we saw some of the quirkiest things that this charming city has to offer. There was SO much to look at during this fascinating tour, that I clearly missed photographing much of it.

The Key West bar scene is bustling! From the open-air Schooner Wharf Bar, a local favourite…

Key West Bar

to the world-famous Margaritaville (have I got you humming the song yet?), located on the world-renowned Duval Street…

Out front Jimmy Buffet's Margaritaville in Key West Florida

to Key West’s “clothing optional” bar, The Bull and Whistle, Old Town Trolley Tours takes you past some of the best watering holes Key West has to offer.

Key West Clothing Optional Bar

Key West Bull & Whistle Bar

Key West is full of whimsical statues, signs and displays. Here sits an old truck (unknown significance).

Key West Tow Truck

As interesting as that truck was, here’s another one that really caught our attention. I’ve seen cars in Canada that resemble this (minus the fish) thanks to rust!

Key West Barnacle Truck

One stop on the tour, at a local hotel, provided me with this photo opportunity – a bell boy lighting his cigarette.

Key West Bell Boy

This gorgeous mural, painted on the side of a building in Key West’s Historic Seaport, is a massive mural depicting the Florida Keys’ underwater world. The mural is painted by world-renowned marine life artist Wyland.


We loved our ride with Old Town Trolley Tours, but truly, the best way to explore all that Key West has to offer, is by foot. We parked our car on one of Key West’s side streets and spent the afternoon walking…everywhere. By the time evening rolled around, we had walked clear across Key West, from shore to shore, three times! This is why you need comfy walking shoes!

Key West Mallory Square Sign

These signs advertise just a few of the fun shops and attractions you will find in the Mallory Square area of Key West.

Key West Florida Signs

The first place noted on this sign is the Key West Sponge Market. That’s where I ran into this guy.

Key West Sponge Man

This guy was a little better looking….plus his store was fun to browse in!

Key West Shell Guy

I found this lady standing off on her own. She had obviously been busy shopping that day. She reminded me a little of Queen Elizabeth – without the crown and jewels of course!

Key West Lady

We found these two dancing out front the beautiful Key West Art and History Museum.

Key West Dancing Couple

These handsome birds are EVERYWHERE in Key West.

Key West Roosters

You never know when you will see one walking by.

Key West Florida Rooster

Roosters are so revered in Key West, you’ll find their image on everything.

Key West Metal Rooster

There’s even the fabulous Funky Chicken Store where the owner told us about the trouble she has with “serial shirt unfolders” (lol).

Key West Rooster T-Shirts

There are so many fun shops and attractions to explore in the Mallory Square area of Key West!


The Key West Aquarium is a great attraction to explore, especially if you want to get your hands wet!

Key West Aquarium

Just be careful not to get your hands wet in this tank!

Key West Aquarium

As the sign says, Mallory Square is “where the sun sets and the fun begins”.

Key West Man On Bike

We did not get a chance to visit the Key West Shipwreck Museum but, just had to take a photo of this interesting wooden building.

Key West Shipwreck Museum

We ran into this “smoking hot” dude on Duval Street.

Key West Cigar

We tried a few varieties of Key Lime pie while in the Florida Keys, however, we missed out on trying Key Lime Pie on a stick. Apparently this is quite a tasty treat.

Key West Key Lime Pie On A Stick

One place everyone needs to visit while in Key West, Florida is the Southernmost Point. Standing in this spot, you are only 90 miles from Cuba. So close and yet so far! Best to hit this attraction in the morning hours for the best lighting for photos. We visited in late afternoon. With the sun behind me, our photos turned out too dark. Also, be prepared to stand in a line up to have your photo taken beside this iconic landmark. Want to see it for yourself now? Check out the Southernmost Webcam!

Key West Southern Most Point

Key West. Their motto should be “worth more than just one day”.

If you go to Key West, don’t do like we did and only spend one day is this fabulous city. Sure, we packed a lot in during our visit there but, we missed many things I would loved to have seen and done.

We did very little shopping yet, Key West is full of all kinds of fascinating shops, especially along Duval Street, and in the Mallory Square area. There were many Key West activities and attractions that we would have loved to experience, like my friend Ann from Kickass Living, who got to spend time out on the water with Sebego Watersports.

Sadly, we missed out on happy hour in Key West. A great little piece of advice (which we didn’t heed due to time constraints!) from my cousin, Gale, who winters near Key West – don’t miss happy hour at Alonzo’s. According to Gale, Alonzo’s has “the best deal in town for the best sea food”. The other piece of advice from Gale that I love? If you can’t make it to Alonzo’s, “just never miss happy hour anywhere in Key West – and walk it off during full price hours!”

That settles it. We’ll just have to head back to Key West – just to experience happy hour!

Have YOU ever been to Key West? What would you recommend as a “don’t miss” attraction?






Disclosure: Many thanks to Jerry from LMA and his team from Visit Florida and The Florida Keys & Key West for facilitating our wonderful day in Key West, Florida!









  1. April 5, 2016


    It certainly looks like you made the most of your time there! I love all the photos. Never visited – but suddenly thinking about it, and searching for that shaker of salt.

    • April 5, 2016


      Hahaha!! The salt!! Love it!! You’re right, we really did make the most of our time there. We didn’t leave until after dark. I don’t think we could have packed more into a day. And….terrific exercise too! Thanks for stopping by, Louise!!

  2. April 5, 2016

    Pam Dafoe

    Thank you for the memories Sandi. It was a long time ago since I was at Key West. I love the key lime pie. It is a great place to spend time at!

    • April 5, 2016


      My pleasure, Pam! I’m so glad you’ve had the chance to visit. It’s such a beautiful part of the world. I am sad to think what rising sea levels will do to this piece of paradise. I tell everyone I know – go while you can! As for the Key Lime pie…that’s the best! I even brought home key lime juice so I could make my own. It lasted me for 3 pies 🙂 Thanks so much for stopping by, Pam!

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