An Unforgettable Road Trip to Key West

sunset on Islamorada Florida Keys

This post is a journal of the day’s sightseeing and experiences.  I also wrote some travel guides to help you on your next trip to the Florida Keys. You’ll find these linked at the bottom of this post.

I visited Key West once before in the late ’90s; however, my husband had never been there before.  He told me he wanted to see the Seven-Mile Bridge as he had seen it in the True Lies movie with Arnold Schwarzenegger. 

I’m sure vacations have been planned on less. So we drove from Orlando, where he had just finished with a business conference, to Islamorada. We spent the night there before continuing our road trip to Key West.

Now before I continue, I thought I should put in a small disclaimer, just in case you’re reading this as a bedtime story to your kid or something.  

Disclaimer: There are references to nudity and naked bodies in this post; if that bothers you, read one of my other posts instead.

Morning of our Florida Keys Road Trip

We packed up our camera gear, drone, swimming clothes, bottled water, and sunscreen and headed out the door!  First stop was coffee and breakfast at the Midway Cafe and Coffee Bar in Islamorada. 

I order some avocado toast and key lime pie for breakfast and a bottomless cup of coffee. I love a bottomless cup of coffee.

When I received my key lime pie, I was surprised to see it made with an actual pastry crust, not the graham cracker crust I was used to. You can read more about why that is in my post on finding the best key lime pie in the Florida Keys

I enjoyed breakfast at the Midway Cafe and recommend you stop when you’re in the area. They have a little space where they sell handmade jewelry and other locally crafted items.  It’s a brightly-colored, sunny spot, perfect for enjoying some coffee before heading to Key West.

midway cafe mug and key lime pie

Some say this is the traditional way to make a key lime pie.

After we finished, we went out to the car, where hubby was so excited to be driving a convertible Ford Mustang for our road trip.  He made sure I took a few photos of him driving, and of course, we had a Florida road trip playlist that included “Ice Ice Baby.”

Back on the Road

 It was great fun driving with the top-down and the wind blowing in our hair.  However, I will say we didn’t leave the top down for our entire day of driving.  For one thing, it is just too hot! And second, my hair-whipping about into a frantic rat’s nest did get old after awhile.  It is still a lot of fun, and I recommend it if you get the chance for a free upgrade, like we did, to go for it!

man driving in convertible

Hubby loved driving with the convertible top down, wind in his hair.

Photo Stop at Duck Key

 This one made me laugh, so I took a picture of the sign.  Little Duck Key, get it? Hmm, perhaps you had to be there.

Little Duck Key road sign in Florida Keys

I love the play on words. The Florida Keys have lots of interestingly named Keys, which is part of the fun!

Hubby brought his drone, and we did a lot of research, including using apps that tell us whether it is okay to fly, what times of the day is better, and then we also read the local forums to find out where local Floridians went to fly their drones.  

Unfortunately, there have been some not-so-bright drone owners who have flown their drones into restricted areas such as airports and other places most people would never dream of doing! This creates a very complicated and restrictive process for the rest of us drone owners.

So, after doing our do-diligence, we found a spot along the old seven-mile bridge that, according to locals, was approved for drone flying.  We walked a little way up the bridge, away from other people (although there were some other tourists who at first gathered around hubby, as the drone always seems to bring spectators).  

Once hubby felt we were a safe distance from people, and he had an open area to land when needed, he put the drone up in the air.

man walking up old seven-mile bridge in Florida Keys

Walking the old seven-mile bridge. Beautiful, but hot!

The Heat Makes Me Crabby

I’m not sure how long we were out flying, but we did walk as far as we could on this section of the old seven-mile bridge, and needless to say, when I left the car, I had not planned on spending so much time walking in the hot sun.  I didn’t put on sunscreen when I left this morning, as we headed to breakfast and then I thought I’d apply it afterward. I forgot.

So, now my shoulders are turning a bright red, and my feet are tired from walking miles on concrete, and I’m getting a little crabby.  This always seems to happen when overheating. Hubby and I discussed this once when we were in Thailand. We were walking up the road in Koh Lanta, headed to a “secret” beach, and he mentioned how heat affects the way people act.  

Sure enough, about 5 minutes into our walk, the conversation turned into a “whose idea was it to walk here anyway” argument.  However, soon, we reached the beach, and as soon as we cooled off in the beautiful turquoise water, our attitudes were miraculously back to cheery and chipper.  

That was how my walk back on the seven-mile bridge went. Of course, after I got back to the car, drank some water, put on some sunscreen, and turned on the a.c., I adjusted my overheated attitude, and we were on our way again.

This is, of course, the side social media doesn’t typically show.  You see us in the pictures smiling together and looking like we never have a care in the world.  Uh, no, we’re humans, only humans.

Sombrero Beach in Marathon, Florida.

Sombrero Beach in Marathon, Florida.

 Next stop Sombrero Beach

Sombrero Beach is reportedly one of the best beaches for swimming in the Florida Keys.  For those of you who don’t know, the Florida Keys are formed from a protected reef system.  In short, there are very few swimmable beaches here. Often, sand is brought in to form man-made beaches.  So we headed for Sombrero Beach in Marathon, to check it out.

When we arrived, we found it under construction.  The restoration project looked like it was in its final stages, and it appears to be a fantastic place to bring the family and spend the day.  The one area you could still access had people swimming and sunbathing, so I’m sure this beach is a popular one and even more so once the restoration project is complete.

I hand hubby my camera for a little bit, not sure why.  He took this “artistic” photo. I’ll let you see if it speaks to you.

plastic dinosaur on Sombrero Beach in Marathon Florida

“Beach Art”

Key West Here We Come!

With all the time we’ve had in the sun, we now prefer to sit in the air-conditioned car.  So we decide to keep on rolling until we arrive in Key West. We can see anything we miss on the way back.  A road trip through the Keys is about the journey, not the destination.

We Have Arrived!

We arrive in Key West and make our way for Old Town. Usually, I drive closest to my first sightseeing stop and then find a parking spot. Since today is Saturday, I navigate hubby to the nearest public parking garage, where we park and instead to walk to our destinations.

This was the best decision we could have made!  We didn’t discover until later, but we arrived in Key West during their Fantasy Fest.  The streets were blocked off for vehicle traffic, and crowds of pedestrians were everywhere!  So, although the heat felt unbearable to a Pacific Northwestern like myself, I was happy we had parked and didn’t get tangled up in the mess of crowds and closed streets.

Lunch Stop

We head for lunch at Caroline’s Cafe on Duval Street. Breakfast was a long time ago, and we are hungry! As we walk there, we notice people carrying folding chairs and dragging coolers behind them.  I say, “there must be a parade today.” Well, I was right, but it wasn’t quite what I expected.

As we cross the street to Caroline’s Cafe, I notice two people walking across the road towards us.  I also see they have no clothes on. Their bodies are painted with patriotic “clothing,” stars and stripes “shorts” and giant “stars” up top. I think, hmm, that’s interesting, have we stumbled onto some Mardi Gras festival?

Let me say before I continue, that lunch was fabulous!  I had the blackened chicken pasta, and it was SO good!! I highly recommend it if you are ever in Key West.

blackened chicken pasta

This blackened chicken pasta was so good! Hubby kept nibbling off of my plate as it was better than his Cuban sandwich.

Lunch-time “Sightseeing”

So, as we sit down to order, I notice the people at the table directly across from us, are also wearing painted “clothing.” Now, I’ve been to Europe, seen lots of statues, and even a few nude sunbathers, but this, this was not something I had seen before. We’re Americans. We don’t do public nudity.

So as I notice more and more people with their painted on clothing.  Hubby leans across the table and tries to oh-so subtly tell me to look behind me. I think in my head, “Um, what could you possibly show me that I haven’t seen yet!” So I peer over my shoulder, in an “I’m not turning to look at you” sort of way and see another naked painted person.  

It’s at this point that I realize my husband doesn’t know that he is surrounded by naked people.  This is quite funny to me. So I also oh-so-subtly give him the nod to look at the table right next to us.  A lot of glitter and paint–that is all my friend. Glitter and paint.

I will note here though that the men all have a grass skirt or some other covering for their lower front regions.  Their backsides, not so much.  

rooster under the table at Caroline's Cafe in Key West

The resident rooster and vacuum cleaner at Caroline’s Cafe.

The Emperor’s New Clothes

 So, as the realization hits my husband, he says, “they’re naked!”  Yep. Bingo! He thought they were actually wearing something. Nope. Nothing but paint.  He made a trip to the restroom while we waited for our check and saw the line of people waiting to be painted.  As you can imagine, the people in line were wearing, um–the Emperor’s new clothes. Of course, the difference between them and the childhood story’s character was that they knew they were naked. They were naked as j-birds.  

After lunch, we discussed his newfound realizations, and we laughed as he and I certainly had a new experience on this trip to Key West.  We saw things we’d never seen before. I guess that’s what traveling is all about! We also discussed the problems that might arise from the lack of clothing.  

Like where do they put their credit cards and wallet?  Does every painted person bring a clothed person with them to carry stuff?  What happens if they sweat or get wet? This question’s answer was discovered by hubby’s trip to the restroom, where he saw a sign stating that the paint was waterproof.  Phew! That could have caused some problems.

Fantasy Fest

Fantasy Fest was created over 40 years ago as a way to increase tourism during Key West’s slow season.  So every October for ten days, the city turns into a festival that is a mixture of Mardi Gras meets Halloween.  The final weekend of the festival, which we just happened to arrive on, is when they block off a section of the city, for an adult-only area in which nudity laws are “relaxed.” 

This is only in the sectioned off portion of the city and only during Fantasy Fest.  We did not see any children in this area, or much at all, which of course makes sense.  So, should you plan to visit Key West, during the off-season, you may want to keep this in mind when making your travel plans.

And in case you’re wondering how much people pay for their paint jobs, prices range from $100 to $1000. This depends on how much of your body is painted and how detailed of a design you want.

Kapok Tree in Key West

We left the restaurant and headed in the direction of our next stop, Ernest Hemingway’s former Key West residence.  As we walked there, the heat felt unbearable. Soon I began to think there might be something to wearing no clothes.

Kapok tree Key West

A Kapok tree in Key West.

We passed this beautiful Kapok tree, which reminded me of the banyan trees in Maui.  It was a nice place to stop in the shade. We kept crisscrossing the street to follow the shady side of the road.  That is how hot it was in Key West. I later learned that they had a 234-day hot streak this year.  During that time, Key West had temperatures at 80 degrees Fahrenheit or warmer. 

Ernest Hemingway’s Home

When we finally arrived at Ernest Hemingway’s home, we discovered you had to pay in cash.  We did not have any cash, and I was okay skipping it (when I’m hot and tired, I tend to lose interest). However, hubby asked the woman at the ticket window, “is it air-conditioned inside?” She replied “yes” that it was, and there was also an ATM around back to get cash.  Well, that was enough for him. He heard the magic words “air-conditioned” and might have paid any price to get some reprieve from the heat.

Ernest Hemingway's Home in Key West

The former residence of Ernest Hemingway.

So I got the cash, and we went inside where it was nice and cool. The inside of the home is decorated with some of Hemingway’s original furnishings. And on display are also some of his books, his typewriter, and movie posters from the many movies adapted after his books.

There is a swimming pool outside the house that calls to you to jump in; however, this is, of course, not allowed.  We peeked inside Hemingway’s writing studio. I told hubby how nice it must be to have an entire studio dedicated to writing.

Soon, our tour was over, and after another stop in front of a fan, we went out into the heat to continue our sightseeing.

Southernmost Point in the Continental U.S.

Because it was hubby’s first trip to Key West, I thought he should go to the Southernmost Point in the Continental U.S.–just to say he had.  As we walk, the sweat drips down our faces, and my husband assures me he does not need to walk all the way to the Southernmost Point.  However, we were almost there, so we might as well finish.  

We arrive only to discover there is a line, a line of people who all want a picture with the marker that shows they are at the Southernmost Point in the Continental U.S.  It is crazy hot out! Hubby and I stand across the street in the shade, neither of us have any interest in standing in the hot sun for this photo opp. 

Southernmost Point Key West

The line stretches outside the frame. The heat is underrepresented in this photo.

We also conclude that we are way too hot, tired, and sunburned to walk back across town.  It is at that moment, a man pedaling a rickshaw comes down the street, we ask him if he can take us to our next stop, the Key West Key Lime Pie Company. Thankfully, he says yes, and we hop on board!

Our driver pedals away almost effortlessly and chats with us about Key West and all the local sites.  He said that this is cool, fall weather compared to the summer, where it can get over 100 degrees Fahrenheit, plus humidity!  Yikes! Note to self, never visit Key West in the summer.

He takes us as far as he can before the closed roads prevent him from going further, and we thank him for the ride.  This is the best $20 I have spent in a long time. 

Key Lime Pie in Key West

We continue through the crowds, passing creatively painted people to make our way to the Key West Key Lime Pie Co.  The man behind the counter is so friendly and welcoming. We purchase one of their mini key lime pies to share. The man pipes freshly made whipped topping on it before serving it to us. Yum!

Mini key lime pie from Key West Pie Co

The freshly piped whipped topping was a nice touch to this mini key lime pie.

We enjoy our pie and ice-cold water before walking down the street to our next stop, Kermit’s Key West Key Lime Shoppe.  Yes, I have more key lime pie, all in the space of 10 minutes. I’m pretty sure I’ll sweat the calories off anyway!  

We sit down to share a slice of key lime pie at Kermit’s. The pie at Kermit’s is everything I looked for in a key lime pie.  Wonderful tart lime flavor with a buttery graham cracker crust–delicious!  

Driving Back Through the Florida Keys

It is late afternoon, and with the parade just around the corner, we both agree we’d rather not get stuck in traffic. Although we may not have hit all of the sights in Key West, we certainly have had a unique experience. So we make our way in the heat to the parking garage, excited to turn the air conditioning on and begin our drive back to Islamorada.

We enjoy the drive back through the Keys, put the top down again, turn up some fun Latin music, and pretended to be carefree teenagers. Of course, we had to stop for selfies at this giant lobster, and we weren’t the only ones. Another man in a red convertible Chevy Camaro stopped and asked if we’d take his picture with the giant lobster too. Nothing like sunshine and warm breezes to make you feel like a kid again!

selfie with giant lobster

Who can pass up a selfie with a giant lobster?

We end the evening with a gorgeous sunset while watching a thunderstorm across the water in the distance. It was a fun day!  

One thing is for sure if you travel with me, things are bound to be interesting! This was undoubtedly one unforgettable road trip to Key West. Here are some more ideas for what to do during your trip to the Florida Keys and make sure to discover where to get the best key lime pie in the Keys too.

Collect Memories, Not Things!

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