There are few drives as epic as the one from Miami to Key West. This journey along the legendary Overseas Highway takes you into the heart of the Florida Keys. It leads directly into the Atlantic Ocean. For me, the chance to visit the home of prolific American writer Ernest Hemingway made it a no-brainer—it was time for a road trip!
It’s so good, I’ve done this trip multiple times just for the joy of it. This time, I flew to Miami, rented a car, and set off on U.S. Route 1, ready to explore the 100-plus miles of the Florida Keys. The highway connects 43 small islands, each one a stepping stone to our final destination: Key West at Mile Marker 1, the southernmost point in the continental United States. From here, Cuba is just 90 more miles away.
Driving on the Legendary Overseas Highway
The Overseas Highway, also known as U.S. Route 1, is a true engineering marvel that takes you on a 113-mile journey through the Florida Keys. This incredible road seems to lead you directly into the Atlantic Ocean, connecting 43 islands all the way to Key West at Mile Marker 0.
As you drive, you’ll feel like you’re floating on water, especially on the famous Seven Mile Bridge. This iconic bridge is the most well-known section of the highway, a long, concrete strip that stretches seven miles between islands and offers breathtaking panoramic views. On either side, you can spot the remains of the original Flagler’s Over-Sea Railroad, a historic piece of the Keys’ past. Stop for a tour!
The road truly is unlike any other in the world. It’s one of those drives where you may wish you weren’t the one behind the wheel so you could fully take in the scenery. We passed countless cars pulled over to the side of the road, their occupants marveling at the unique experience of standing in the middle of the ocean with nothing but water and sky in every direction.
Things to Do in Marathon Key
After a few hours on the road, you’ll be ready to cool off. If you done like me and listened to Jimmy Buffett on repeat, you’ll know your first major stop has to be Marathon Key. Jimmy, the pirates, and the Parrotheads had it right: Marathon Key is a great place to stop and maybe even stay a while.
Spanning 13 islands from Mile Marker 47 to 60, Marathon is the central heart of the Florida Keys. It’s a popular hub known for its beautiful turtles, long sandy beaches, and lush mangroves. Beyond the stunning natural scenery, you’ll find plenty of attractions, including the Dolphin Research Center, the Turtle Hospital, a wild bird rescue, and a natural history museum.
Marathon is also home to the picturesque Sombrero Beach at Mile Marker 50. With its swaying palms and brilliant white sand, this beach is exactly what you picture in your tropical fantasies. The beaches in Key West simply don’t compare, so be sure to make a stop here to stretch your legs and feel the sand between your toes!
How to get around Key West
Once in Key West, you might consider using bicycles as your primary mode of transportation because parking can be tough. With the island being only about 4 miles long and just over 1 square mile in size, it seemed like the perfect way to explore. I’ve done this. That plan, however, lasted for exactly one day before I rented a Vespa instead.
The thing about Key West is that it’s intensely hot. As the southernmost point in the continental U.S., its climate is similar to a tropical savanna. I’d compare it to living inside a sauna hot enough to bake bread.
Fun fact: Be prepared to dodge colorful roosters. The birds are frequently seen foraging for food on Duval Street and in restaurant patios.
While the island is surrounded by water, even the ocean offers little relief. Jumping in at the shore will not cool you down much. The salt water feels more like a lukewarm bath than a refreshing swim. A better way to escape the heat was to get further out into the water. I hopped on a boat. It was headed for a snorkeling adventure at the reef.
Snorkeling the Coral Reef of Dry Tortugas National Park
The day long tour took me out into the turquoise waters, home to the third-longest barrier reef in the world after Australia and Belize. Snorkeling this coral reef is an absolute must-do in Key West. The coral is spectacular, stretching for miles around Dry Tortugas National Park. Located west of Key West in the Gulf of Mexico, this unique park is made up of several islands, Fort Jefferson, and vast, shallow waters filled with exquisite coral.
The reef was stunningly beautiful, teeming with sea stars, turtles, conches, and fish of every color. It was the most elaborate coral and marine life I had ever seen. The massive coral formations attracted a variety of sea creatures. This included a five-foot-long reef shark. It approached from about 20 feet away. Although the snorkel guide assured me it was harmless, my brain had other ideas. I spent the rest of my time tense and on high alert, practicing underwater punches in case the “stray dog” (as she called it) decided to return.
Kayaking and Paddleboarding Through Mangrove Tunnels
While getting around on land was a challenge, I found a new way to explore the Keys’ scenic backwaters: by kayak and paddleboard. These are the only vessels capable of navigating the narrow channels, including the beautiful Salt Pond near Key West.
My paddle through a mangrove tunnel was a short one, but it ended with a huge payoff. The shallow waters on the other side were teeming with fascinating life. I saw upside-down jellyfish and starfish. There were also crabs, sea sponges, and sea cucumbers. It was an incredible sight, even in the blistering midday sun. The sun’s intensity exceeded my expectations. My skin was burned despite my best efforts.
Even with the heat, I thoroughly enjoyed getting an up-close look at the vibrant ecosystem of the mangroves. I discovered a hidden world of exciting creatures.
The Hemingway House
For any literary fan, a visit to the Ernest Hemingway House is a must. The prolific writer bought the Spanish Colonial-style house in 1931. He lived there for eight years. It is now a museum dedicated to his life and work.
A tour of the property allows you to explore the house. You can also walk through the lush back garden. The highlight for me is his writing room. Hidden above the garden in what looks like an adult treehouse, I imagined Hemingway sweating in the heat. He pounded furiously on his typewriter. His prose became concise and dreamy through a mix of heat-induced delirium and alcohol.
You’ll notice the shoddily built brick wall that surrounds the property. Hemingway and his friends constructed it over several drunken afternoons. They wanted to keep gawkers from knocking on his door. The gardens inside are a delight to explore. They are full of tropical plants and quirky fountains. One fountain is fashioned from a urinal he repurposed from his favorite bar.
Another unique feature of the home is its famous residents: the 50-plus polydactyl (six-toed) cats that roam the grounds. These friendly felines are descendants of Hemingway’s own beloved cat, Snow White. They have free rein of the property and bask in the attention of visitors.
Fun Fact: Another literary icon, Judy Blume, also lives in Key West! You can find her bookstore, Books & Books, at 533 Eaton Street.
Key West Cemetery
The Key West Cemetery is located in the heart of Old Town. It is a fascinating and often-overlooked stop on any trip to the island. More than just a final resting place, it’s a living museum of Key West’s unique and quirky history.
Because of the rocky soil, many of the tombs are above ground, leading to a unique architectural style reminiscent of New Orleans’ cemeteries.
Fun fact: The island’s large green iguanas love to sun themselves on the large, hot stones – be prepared!
The Key West Cemetery is most famous for its irreverent and witty epitaphs, which perfectly capture the island’s bohemian spirit. As you wander the grounds, you’ll find headstones with inscriptions like:
- “I Told You I Was Sick”
- “I’m Just Resting My Eyes”
- “If You’re Reading This, You Desperately Need A Hobby”
The Key West Cemetery is an active burial ground, with new interments happening every year.
Sunsets at Mallory Square
No trip to Key West is complete without experiencing the nightly Sunset Celebration at Mallory Square. This free event begins about two hours before sunset. It is located at the western end of Duval Street. It’s a must-do for anyone visiting the island.
Every evening, a diverse collection of street performers, artisans, and food vendors gathers to celebrate the sun’s descent. The energy is infectious, with crowds of people lining the harbor to watch the show. You’ll find everything from tightrope walkers and jugglers to magicians and animal acts. Live music fills the air as local artists sell their work and food carts offer snacks and drinks. The fresh smashed guacamole is to die for.
Nightlife and Duval Street
If you’re looking for a good time after the sun goes down, Duval Street is the place to be. The street is the pulsing heart of Key West’s nightlife, home to an incredible concentration of bars and restaurants. It’s where the famous “Duval Crawl” originated. This legendary bar-hopping adventure is as wild and memorable as its name suggests. I can attest to its excitement. The atmosphere is electric, with live music spilling out of open doors and a constant stream of people flowing from one spot to the next.
Sloppy Joe’s and Captain Tony’s Saloon
No writer can visit Key West without following in the footsteps of Ernest “Papa” Hemingway. My first stop is always Sloppy Joe’s Bar, arguably the most famous watering hole in Key West. Located on Duval Street, it’s known for being one of Hemingway’s favorites. While it looks much like it did in his day and still serves its signature mojitos, it now has a souvenir shop and is a non-stop hub of tourist traffic.
However, many people don’t realize that the current Sloppy Joe’s isn’t the original location. Hemingway frequented the bar when it was just a few doors down. The original location is now Captain Tony’s Saloon. This historic spot still feels like a classic, no-frills Key West bar, complete with a unique history (bras hanging from the ceiling) and a tree growing right through the middle of the building.
Be careful here. The first time I visited the musician inside singing and playing the guitar noticed me from the street.
“Are you coming in?” he asked. It ended with me 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, but the drive is epic.
Anonymous
October 2, 2023Rene, remember this is the most Southern point on the Continental U.S. If you want to visit the real most Sothern point of the U.S. then a trip to the Big Island of Hawaii is in store. This is several 100 miles further South, but the Trade Winds will keep you cooler there. Plus, not far from there is the Mark Twain’s Monkey Pod tree. He planted it when he visited to get Insite of the Islands. Originally only going to stay for 3 months, ended up staying for 3 years. He’s the one who dubbed Waimea Canyon on Kuai the Grand Canyon of the Pacific. A must see adventure!!!