A trip to Key West, a place like no other

In Key West you find six-toed cats, free-roaming chickens and sunsets that are celebrated each night. And winter never gets this far south, the summers are endless. This island is like no other place in Florida, the US or even the world.

Duval Street and Whitehead Street are contrasting parallel streets that crosses Key West. If you get to know them, and the contrasts they offer, you get a certain understanding of what the island is all about.

Key West has its own quirky and laid-back culture. Here you are welcome to come as who you are whenever you are. It’s always five o’clock somewhere!

Key West from above
The paradise island Key West.

The paradise island with more than just great weather

Key West is an island in the Florida Keys. Even though it’s an island you can reach it by car, as it is connected by US Highway 1 with the mainland. The drive from the mainland is great, but flights and boats also go there.

The location means that Cuba is less than 100 miles (160 km) away, which is closer than Miami. Its southern location also means that weather stays warm every month of the year.

In January the daily average maximum temperature is 74 degrees Fahrenheit (24C), and even at night the temperature on average only goes down to 64 degrees Fahrenheit (18C). And that’s the coldest month of the year!

But the main attraction of the Florida Keys has more to offer than wonderful weather. Here you find a unique charming quirky vibe and something for anyone to explore.

Pelicans in Key West
Pelicans enjoying the warm Key West weather.

The heart and soul of Key West

The two main streets in Old Town, Duval and Whitehead, offer great contrasts. Exploration of both is needed to better grasp what the island is about. While Duval Street is the famous and buzzing street, the more low profile Whitehead shows another side of the quirkiness that defines Key West.

Duval Street

Duval Street is the centre of attention, and it goes north to south, from the Atlantic Ocean down south to the Gulf of Mexico.

When you walk down Duval Street you walk in the heart of Key West. Here you find a wide selection of restaurants, bars and retails shops. The road is only 1.25 miles (2 km) long, but full with terrific places to eat and drink.

The most famous bar of them all is Sloppy Joe’s Bar. It’s the renowned bar that Ernest Hemingway used to go to. Hemingway’s favorite Key West watering hole has been found on the same spot on Duval since 1937.

Sloppy Joe's Bar in Key West
Hemingway’s favorite watering hole, Sloppy Joe’s.

The saying that the clock always is 5 PM somewhere feels as meaningful as it possibly can on Duval Street in Key West. Here you always can find reasons and possibilities to sit back and enjoy yourself, no matter what time it is.

On Duval you always find something going on. The summers are endless in Florida Keys and so is the business of Duval Street.

Key West villa
A typical villa in Key West.

Whitehead Street

If Duval Street is the heart of Key West, Whitehead Street is its soul. Whitehead Street goes parallel with Duval Street, one road in the western direction.

This road is not commercialized like Duval Street with its shops, restaurants and bars everywhere your eyes go. Instead, the street is rather quiet and lined with old-fashioned bungalows in beautiful bright colors. This street, as many perceive as just a side street to Duval, is as important to the Key West identity as the buzzing neighbour.

Here you find Ernest Hemingway Home and Museum and the lighthouse, located on different sides of the road. Hemingway often needed the lighthouse to be able to make it home from his favorite bar, Sloppy Joe’s. Conveniently so, he just needed to follow the light to get back home.

Whitehead Street in Key West
Whitehead Street in Key West.

On Whitehead Street you find the famous Mile Marker 0. It’s the end, or the beginning, of US Route 1. It runs along the East Coast of America, from the Canadian border all the way south to the tropical setting in Key West.

Most of Whitehead Street is very quiet, even though it’s just a stone throw away from the always busy neighbor Duval. With its relaxing vibe it’s a great place to dream away and reflect about both small and big matters.

Lighthouse in Key West
The lighthouse in Key West.

But if you want a drink without leaving Whitehead, the Green Parrot Bar is ready to serve you something refreshing. It has stood on the same place since the end of the Second World War. And the bar is appreciated both by locals and visitors from all around the world.

When you follow Whitehead all the way south you get to Southernmost Point. It not only means the end of Whitehead Street, but also the end of the US. The monument in shape of a large concrete buoy represents that you are in the southernmost point of the continental US.

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The unique quirky spirit

Key West has always been a place for freethinkers and most of all it’s the residents that make the place quirky. But some attributes showing the unique quirky Key West way really stand out when you visit.

Sunset celebration

The saying that you should live every day of your life as if it were your last day really comes to life every night in Key West. On Mallory Square every sunset means celebration.

Sunset in Key West
Sunset in Key West.

Six-toed cats

During his days Ernest Hemingway was given the cat Snow White, a white six-toed cat, by a ship’s captain. Today, descendants with the same trait live on the property and pass on the heritage of Hemingway.

Six-toed cat
Descendant to Snow White, Hemingway’s cat.

Free-roaming chickens

Watch out for chickens roaming down the street. The free-roaming chicken population of Key West is to be seen throughout the island. And they seem to enjoy life at least as much as the locals.

Roosters walking the street
Roosters walking the street.

Conch Republic

In 1982 the city of Key West declared itself Conch Republic, as a protest against a blockade set up by the US border patrol on US Highway 1 at the beginning of Florida Keys. And today Key West residents proudly call themselves Conchs, pronounced as “KONKS”.

“I told you I was sick”

When you wander through the cemetery one headstone especially catches your attention. It reads “I told you I was sick”, highlighting that the quirkiness of this place isn’t distinguished by life or death. Instead, it’s a permanent phenomenon.

What not to miss in Key West

Knowing Duval Street and Whitehead street also involves getting to know some of the best attractions on the main island of Florida Keys. But what in particular should be on the Key West to do list?

Mallory Square

Sunsets at Mallory Square is a great Key West tradition. Here you can spend the last hours of the day watching the sun sink lower and lower into the Gulf of Mexico horizon, creating beautiful colors in red, orange and pink.

The sunset on Mallory Square is always lively. Food vendors sell food and cold drinks while local performers try to attract the crowds.

Mallory Square performer
A performer on Mallory Square at sunset.

Fort Zachary Taylor State Park

If you prefer a more private moment when enjoying the sunset you should head to Fort Zachary Taylor State Park in the southwest part of the island. There the sunset is as pretty, but without the liveliness of Mallory Square.

In Fort Zachary you also find the best beach in Key West. Nice public beaches could be harder to find than you think in Key West, but this one is a true gem.

Fort Zachary Taylor State Park
Fort Zachary Taylor State Park.

Read more: Our favorite beach in Key West, Florida >>

Southernmost Point

As the name indicates the Southernmost Point symbolises the southernmost point of the continental US. The monument takes shape of a large anchored concrete buoy.

Visitors line up as early as dawn to take pictures of the famous buoy in black, red and white. From breakfast time until sunset a line of tourists appear on the block. All wanting a picture with the monument as a symbol for the ultimate Florida Keys trip.

A map shows you that there are a few points on the island where you are even further south than the monument Southernmost Point. But no matter the exact placement of the monument, it’s amazing to be in the most southernmost point of the continental US, Key West.

Southernmost Point monument
Southernmost Point in Key West.

Ernest Hemingway Home and Museum

The property where Ernest Hemingway used to live is fascinating to visit if you want to know more about the author himself or simply want to know more about life on the island during those days.

Hemingway himself beautifully stated that: “every man’s life, told truly, is a novel”. When you hear the entertaining novel about him you also learn some of the story about Key West.

Read more: Come and see how Ernest Hemingway lived in Key West, Florida >>

Hemingway's House in Key West
Hemingway’s House in Key West.

Sloppy Joe’s Bar

Among all bars on the island, Sloppy Joe’s is on top of the list. It was founded already in 1933, and Ernest Hemingway soon made it his favorite watering hole.

But Sloppy Joe’s location on the island was originally across the street from the current location. The move to today’s location was made in 1937, when the owner moved the establishment to avoid a rent increase. A raise from three to four dollars a week might not sound as much to fight about today, but back in the days it was a significant amount of money.

Nevertheless, Sloppy Joe’s after the move found its perfect spot in the heart of Duval Street. The bar contributes to the buzz of Key West with refreshing drinks and live music. Here you have all you need for a good night out, just like in the days of Hemingway.

Mile Marker 0

The US Highway 1 zero sign is one one the most photographed spots in town. This place marks the end, or the beginning, of the highway that goes for 2,369 miles (3813 km) from the Canadian border all the way down to Key West.

Mile marker zero
Mile marker zero.

Dry Tortugas

Key West is the last island in Florida Keys that you can reach by car. But it’s not the last island in the Keys. Dry Tortugas is a small group of paradise islands that are located even further west.

Here in Dry Tortugas National Park you can explore amazing scenery and the historically Fort Jefferson. Though technically almost 70 miles from Key West, the seaplanes and boats depart from there and a day in the very outer part of the Keys is a fun addition to a Key West trip.

Where to stay in Key West?

If you stay in Old Town, which is on the western part of the island, you have most attractions nearby. Therefore you can relax and not have to think about driving or making it in time for a shuttle to get around.

But if you don’t plan to spend much time in Old Town it could be a good option to stay in the eastern parts of Key West to get better hotel rates. Generally, the further away from Duval Street the better rates you find.

The southern part of Duval closer to Southernmost Point is good if you prefer it quiteter. For more action right at your door steps it’s better to stay at a hotel near Mallory Square on the north end of Duval.

Click here to check accommodation options and hotel deals in Key West.

Southern part of Duval Street
Southern part of Duval Street.

How to get around on the island

The size of Key West is perfect for a laid-back vacation. If you stay in Old Town you have walking distance to Duval Street and Whitehead Street, which means that you are close to most things to do. Therefore having a car while visiting isn’t neccessary or even optimal.

To tour the city you can easily walk, bike or take the old town trolley tour. The latter is a hop-on and hop-off trolley which takes you to some of the most interesting places of Key West in a convenient way.

Enjoy all that Key West has to offer

While endless summer alone is a great reason to travel to the Keys, there is much more on offer than just the warm weather. So visit the interesting places that the island has to offer, and enjoy the quirkiness that rests over all of Key West.

And remember that it’s always five o’clock somewhere and that five o’clock is best spent in Key West!

Road to  Key West
You can take the car and make a road trip to Key West, or go by plane or boat.

Read more: The Florida road trip from Orlando to Key West >>

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