Driving the Overseas Highway to Key West is among the most epic drives you can take in the United States. Key West was also home to prolific American writer Ernest Hemingway, so, for me, it was a no-brainer – road trip time!

My daughter Autumn and I flew to Miami and rented a car to drive the Overseas Highway on U.S. Route 1 through the Florida Keys.

The highway leads you over 100 miles directly into the Atlantic Ocean and connects 43 small islands leading to the last – Key West – at Mile Marker One. This is the southernmost point in the United States. If you go any further, you’d be in Cuba (just 90 more miles).

Driving into the Ocean

One bridge, aptly named the Seven-Mile Bridge, spans seven miles between islands. The road is like none other in the world. Long expanses are of nothing but a concrete strip connecting the smallest of islands. As we drove the highway, the sun lowered into the horizon and we drove straight into it.

Have you ever driven into the ocean? It’s one of those drives where you’re better off not being the driver so you can stare open-mouthed at the scenery. We passed many vehicles pulled over to the side of the road to marvel over standing in the middle of the ocean.

Cheeseburgers in Paradise at Sombrero Beach

Just a few hours off the plane and we were already as hot and sweaty as a Finnish businessman.

I’d read Tales from Margaritaville by Jimmy Buffett and listened to the song multiple times in preparation for this trip, so we planned to cool off on Marathon Key. Jimmy, the pirates, and the Parrotheads had it right. Marathon Key is a great place to stop and maybe stay.

Marathon Key is probably the second most popular key. It’s made up of 13 islands, known for it’s turtles, long sandy beaches, and mangroves. There’s also the Dolphin Research Center, bird-rescue center and natural history museum.

There we went to the popular Sombrero Beach at mile marker 50, a picturesque and sparsely populated white-sand beach exactly as you’d picture in your beach fantasy. Beaches on Key West wish they could be this nice. So stop!

We didn’t get cheeseburgers, but we did have some truly awful Mexican food that I’ll never forget as long as I live. Take my advice and stick to the burgers.

How to get around Key West

Once on Key West, we rented bicycles. The island is only about 8 square miles, so we planned for those to be our main transportation mode. That lasted exactly one day before we rented Vespas. The thing about Key West is it’s HOT.

In the United States, Key West is as far south as you can go. That makes it hot. Hot. They say it’s hot like a tropical savanna. I’d compare it to living inside an oven hot enough to bake bread.

As we rode those bicycles around the picture-perfect island, we poured sweat like we were going through a car wash. It wasn’t pretty.

Get a Room with a Pool and Good AC

We were surrounded by water but jumping in the ocean did little to cool us down. In fact, the salt may have actually worsened the situation by further drying out our already dehydrated bodies. The water was hot and salty.

There aren’t many ocean waves in Key West because of the coral reef that protects it. They say the reef also protects it from major storm damage, providing a relief break to an angry ocean. But it also keeps the water as hot as a bath, which might be nice if you weren’t dying from the heat.

We decided to get further out into the ocean for some relief, so we hopped on a boat headed for snorkeling at the reef.

Snorkeling the Coral Reef of Dry Tortugas National Park

The tour boat took us out into the turquoise waters, which are home to the third-longest barrier reef in the world after Australia and Belize. Snorkeling the coral reef off the coast of Key West is something you must do. The coral is spectacular for miles around the Dry Tortugas National Park. It’s the only national park with less than 1% of the park on dry ground.

The reef was amazingly beautiful and filled with sea stars, turtles, conches, and fish colored every rainbow hue. It was the most elaborate coral and sealife I’d seen anywhere. The massive coral formations drew in much sea life, including at least one I didn’t plan for.

Dry Tortugas Natioanal Park

Because it’s west of Key West, the park is actually in the Gulf of Mexico. It comprises several islands, Fort Jefferson and very shallow waters filled with exquisite coral reefs. It is home to sea turtles, seabirds like sooty terns, a sunken ship and several lighthouses.

Shark Jiu Jitsu

Key West is pretty far into the ocean and the ocean is shark land.

I was in my element. Snorkle working perfectly, mask not fogging, fins practically a part of my leg. The kid wasn’t even complaining. (It helps to put her underwater with a tube in her mouth).

Then, I looked to my right, and approaching from about 20 feet ahead was a shark. You have got to be kidding me. It was about 5 feet long and a foot wide. In my non-shark-loving life, that is HUGE.

I know some people, divers, in particular, don’t seem to mind swimming with sharks. I, however, am definitely not one of those people.

Where can you hide in the ocean?

I was like a cartoon character that vaulted straight up out of the water and ran on top of it into the distance far away, never to be seen again.

In a split second, I thought a variety of expletives along with THAT’S A SHARK. Can I outswim it? No, don’t be an idiot. Well, I’m going to have to punch it in the face. Wait. Where’s the kid?

I did a quick scan of the area and swam right to her. I pulled her above the water. “Don’t freak out,” I said. “What?” “There’s a shark.”

“WHAAAATTTTT?!?!?!?!” she screamed while freaking out.

We swam to our snorkel guide faster than a cheetah on the hunt.

“Oh, that’s just a reef shark, they’re like stray dogs. Nothing to worry about.”

It was my opinion that she needed to catch and cage that dog so I could swim in peace. There was no way I could focus on the brain coral when my own brain kept telling me I was about to be attacked from behind by Jaws.

I didn’t see the shark again, but I was tense the entire time I practiced my underwater punches.

Paddleboarding

Kayaks and paddleboards are the only craft capable of navigating some of the Keys’ most scenic backwaters, including Key West’s Salt Pond.

Here, a 10-minute paddle through a mangrove tunnel ends with a big payoff: shallow waters teeming with upside-down jellyfish, starfish, crabs, sea sponges, sea cucumber and other exciting creatures.

We wadded in the water during the midday sun, blistering and severely dehydrated. My skin was as burned as it was able to get. I never burn, but the sun was so much more intense than I expected.

Despite that, I enjoyed the sea life even if the kid wouldn’t get in the water for fear of being attacked by a cold-blooded predator.

Hemingway’s House

Hemingway bought a house on the island in 1931 and lived there for eight years. It’s now a museum about the prolific writer.

You can tour the house, the back garden – and hidden above the yard in an adult treehouse, his writing room. I imagined him drunk, sweating, and pounding the keys furiously, delirium from the heat and alcohol, making his prose concise and dreamy.

We walked around the shoddily built brick wall that surrounds his property. He and some friends built it over several drunken afternoons to keep gawkers like me from knocking on his door.

Inside the gardens are lush and the fountains … interesting. The best is a urinal from his favorite bar repurposed as a flower container.

Also in the yard are about 50 polydactyl cats, descended from his own beloved felines. Meow. Polydactyl cats are born with more than the usual number of toes on their paws – in some cases many more. These cats, with their many extra toes, have free reign of the property and seem to enjoy the attention of visitors.

Hemingway Drinks Across Key West

No self-respecting writer can go to Key West and not follow in the footsteps of Hemingway, right? That means you’re going to the bar.

Sloppy Joes

Sloppy Joe’s Bar on Duval is the best known for being his favorite watering hole. It looks just like it did when “Papa” was alive and still sells their signature Mojitos, but now it also has a souvenir shop and has nonstop tourist foot traffic. What many don’t realize is that it isn’t even the original saloon.

Captain Tony’s

When Papa started going to Sloppy Joe’s, it was actually located a few doors down on Duval at a place called Captain Tony’s Saloon. (The many bars on Duval street are where the term “Duval Crawl” comes from. I’ve done the “Duval Crawl” on a different visit to Key West. It wasn’t pretty and I don’t recommend it.).

We didn’t intend to go into Captain Tony’s; I just wanted to take a look. So we stood outside peering in like kids outside a candy window. That’s when the charming fellow inside singing and playing the guitar noticed us.

“Are you coming in?” he asked. I shrugged my shoulders. Then I hear my daughter say, “It’s her birthday!” It was, in fact, my birthday. My fortieth.

“That’s it, you come in here, or I’m coming to get you,” the musician said. Before I know what’s happening, he is holding my hand and pulling me into the bar.

Suddenly I was sitting next to him at the front of the bar holding a small electric fan to make his fair blow while he serenaded me in a raunchy song. The song made the audience hysterical and me somehow even redder through my sunburn.

Such is life in Key West. It’s hot, wild, and anything can happen. What a place.

I’ve been to over 25 national parks. Read other national park stories here.

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