The ultimate guide for visiting Key West, Florida

  • Post last modified:June 22, 2021
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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. Visiting Key West is a trip like nothing else.

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

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Guide for visiting Key West

What to expect when visiting Key West

Key West is an island in the Florida Keys. But 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 scenic, but flights and boats also go to Key West.

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

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

But the main attraction of the Florida Keys has more to offer than wonderful weather. When visiting Key West you find a unique charming quirky vibe and something for everyone to explore.

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

Reasons to visit Key West

Key West in Florida is an amazing place to go to and the reasons to visit are many. Here great reasons to visit Key West are listed.

1. Visit Key West for the endless summer

Key West is known for its endless summer. You can visit Key West and enjoy warm temperatures while most other parts of North America are freezing.

In January which is the coldest month of the year the daily average maximum temperature is 74 °F (24 °C). And even at night in January the temperature on average only goes down to 64 °F (18 °C). That doesn’t sound too cold, does it? The warm tropical climate is one of the best reasons to visit Key West.

Palm tree in Key West
Endless summer in Key West.

2. The perfect holiday size

Key West is about 1 mile (2 km) wide and 4 miles (6 km) long, which means that the size is very suitable for a relaxing holiday. The managable size means that you can focus more on experiencing things instead of spending time on going from one place to another. Because of the convenient size every minute on your stay is fun and that’s a great reason to visit Key West.

If you stay in Old Town when visiting Key West, you have most places of interest within walking distance. And if you don’t want to walk, the Conch Tour Train takes visitors around town.

Conch train in KW
The Conch Tour arriving in Key West.

3. Here it’s always 5 PM

In Key West it’s always a good time to enjoy yourself. The laid-back vibe is a much appreciated part of life here. And you can’t argue with the fact that it’s always 5 o’clock somewhere.

A cold drink and crashing waves
It’s always 5 PM somewhere.

4. Duval and Whitehead Street

The streets Duval and Whitehead in Key West sit next to each other and complement each other very well.

Duval Street is full of good places to eat or drink and for many visitors one of the reasons to visit Key West. Of all places on Duval the most iconic one must be Sloppy Joe’s Bar. It used to be Hemingway’s watering hole and has been on the same spot since 1937.

On Whitehead Street you find fun places to visit such as the Southernmost Point, Key West Lighthouse, Hemingway Home & Museum and Mile Marker Zero. While Duval Street sometimes can get a bit loud, Whitehead Street is less intense but at least as enjoyable.

The lighthouse in Key West
The lighthouse on Whitehead Street.

5. Visit Key West for the unique quirky vibe

Key West holds a since long settled quirky vibe. Here it’s good to be different, and being who you really are should be encouraged. And the quirkiness is not distinguished by life or death. It’s something that you take with you into the grave in Key West. The text on a headstone in the cemetery on the island says, “I told you I was sick”.

Suitingly so, some of the most famous residents in Key West are the quirky six-toed cats that are descendants to a cat of Hemingway’s.

Ernest Hemingway Key West bed and cat
A Hemingway cat.

6. Even getting to Key West is beautiful

The traveling to Key West on the Overseas Highway is a unique experience. The Overseas Highway takes you from the mainland on bridges between all the keys on the way to Key West. An especially iconic stretch is the Seven Mile Bridge that connects Knight’s Key to Little Duck Key. Make sure that you fit in time for stops along the way when you drive to visit Key West!

7 mile bridge to Key West
The Overseas Highway to Key West.

7. The sunset celebrations are reasons to visit Key West

Mallory Square is famous for the sunset celebrations that take place each evening. By celebrating every day, you don’t take the joys of life for granted. And sunsets in Key West deliver the most spectacular show. If you have seen a Key West sunset you know that they are a great reason to visit.

Red sunset in Key West
Sunset in Key West

Exploring the main streets of Key West

The two main streets in Old Town, Duval and Whitehead, offer a lot of fun attractions and great contrasts. Duval Street and Whitehead Street are parallel streets that cross Key West.

If you get to know them, and the contrasts they offer, you get an understanding of what the island is all 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.

Feel the buzz on 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. On Duval Street you find a wide selection of restaurants, bars and souvenir 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.

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 find reasons and possibilities to sit back and enjoy yourself, no matter what time it is.

Key West villa
A villa along Duval Street in Key West.

Stroll the quieter but as charming 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.

When visiting Key West you notice that Whitehead Street not is commercialized in the same way as Duval Street with its shops, restaurants and bars everywhere your eyes go. Instead, Whitehead Street is rather quiet and lined with old-fashioned bungalows in beautiful bright colors. Duval Street, which many Key West visitors perceive as just a side street to Duval, is as important to the Key West identity as the buzzing neighbour.

On Whitehead Street you find Ernest Hemingway Home and Museum and Key West Lighthouse, located just across the road from each other. 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.

The famous Mile Marker 0 is another Whitehead Street attraction. 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’s throw away from the always busy neighbor Duval. With its relaxing vibe it’s a great place to go to when visiting Key West to dream away and reflect about both small and big matters.

And 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 Key West visitors from all around the world.

If you follow Whitehead Street 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 the southernmost point of the continental US.

Lighthouse in Key West
Key West Lighthouse on Whitehead Street.

Best things to do when visiting

Key West is an island that’s packed with fun things to do. Here some of the most important things of all the best things to do in Key West are listed.

Celebrate the sunsets on 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. It’s the perfect place to end a day when visiting Key West.

Mallory Square performer
A performer on Mallory Square at sunset.

Go as far south as you can to 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.

Don’t miss Ernest Hemingway Home and Museum when visiting Key West

The property where Ernest Hemingway used to live in Key West 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 during your visit you also learn some of the story about Key West.

When visiting Ernest Hemingway Home & Museum you also get to make acquaintance to the iconic six-toed cats.

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

Scenic views at Key West Lighthouse & Keeper’s Quarters Museum

Right across the street from Ernest Hemingway Home & Museum you find Key West Lighthouse and Keeper’s Quarters Museum.

Key West Lighthouse offers the best views on the island when visiting Key West. If you climb to the top you get breathtaking panoramic views out over the island.

And a visit to the Keeper’s Quarters Museum adds more depth to a visit. Here you can learn more about the history of the lighthouse, the keepers and the important role it has played for Key West and Florida.

The lighthouse in Key West
Key West Lighthouse.

Check out Fort Zachary Taylor State Park

If you prefer a more private moment when enjoying the sunset you should head to Fort Zachary Taylor Historic State Park on the southwestern 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. This is a true gem when visiting Key West.

Fort Zachary Taylor State Park
Fort Zachary Taylor State Park.

Have a refreshing beverage at 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 when visiting Key West, just like in the days of Hemingway.

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

A fun day trip to Dry Tortugas when visiting Key West

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.

In Dry Tortugas National Park you can explore amazing scenery and the historic Fort Jefferson. Though technically almost 70 miles (113 km) 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.

Blue water, sandy beach and red fort during daytime
Fort Jefferson in Dry Tortugas National Park.

Colorful butterflies at Key West Butterfly & Nature Conservatory

The Key West Butterfly and Nature Conservatory, also known as the Butterfly Garden in Key West, has become one of the most popular attractions when visiting Key West. Here you can stroll through a glass-enclosed tropical garden full of butterflies.

And the butterflies love visitors. More often than not the colorful butterflies will try to land on your back or shoulder when you visit. For an educational experience the butterfly conservatory also has a learning center where you can indulge in all there is to know about butterflies.

Butterfly in Key West Butterfly & Nature Conservatory
Key West Butterfly & Nature Conservatory.

The unique quirky spirit in Key West

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 and that’s one of the many great reasons to visit Key West.

Sunset in Key West
Sunset in Key West.

Free-roaming chickens

Watch out for chickens roaming down the street during your trip to Key West. The free-roaming chicken population 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.

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 Ernest Hemingway property in Key West and pass on the heritage of Hemingway.

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

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 when visiting Key West 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.

Beaches in Key West

The world’s third longest barrier reef protects Florida Keys from big ocean waves. That’s great news for the diving enthusiast. However, for the sandy beach lover that could be negative.

Without big waves the mechanism that creates sand in a natural way is missing. Hence Key West is not known primarily as a beach or surf destination. But do not despair as there still are a few nice Key West beaches to choose from.

The best beach in Key West

Fort Zachary Taylor Beach is generally regarded as the best beach in Key West. The well maintained beach is located in the western end of Key West, approximately a 20 minute walk away from the always busy Duval Street. As the Key West beach is part of a state park there is a small fee to enter.

Right at the beach there is a café, picnic tables, grills and restrooms in case you need a break. In other words the Key West beach has what you need to spend a full day there.

Picnic tables at Key West beach
Picnic tables in very appreciated shade.

At Fort Zachary Taylor Beach you also find the iconic mile marker sign reminds you about that Key West is situated closer to Cuba than to Miami.

Key West beach sign during daytime
The famous mile marker sign.

Other beaches in Key West

There are free beaches to visit in Key West as well. Higgs beach is one of them that’s conveniently located near Old Town. Another free Key West Beach is Smathers Beach, which is located a bit further away.

It’s also worth to point out that there are many private beaches in Key West. These are attached to hotels or private homes.

Beaches higher up in the Florida Keys

You find some beach gems in the other part of Florida Keys as well. Bahia Honda Beach is located about 35 miles and a little less than 1 hour away by car. Even further up in Florida Keys you find Sombrero Beach which is another great Florida Keys Beach.

How to get around in Key West

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

To tour Key West 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.

Southern part of Duval Street
Southern part of Duval Street.

Where to stay when visiting

There are many great places 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 but still central. 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 when visiting Key West.

Booking.com

Driving to Key West

The Overseas Highway is the southermost part of US Highway 1. It takes you the 113 miles (182 km) from the mainland all the way down south to Key West. And driving the Overseas Highway with its scenic views is the most spectacular way to get there.

Along the impressive highway there’s a lot to do apart from enjoying the amazing views. Key Largo, Islamorada, Marathon and the Lower Keys area before you get to Key West are great places for stops.

Key Largo

The Key Largo area is known as the gateway to Florida Keys. John Pennekamp Coral Reef State Park and the African Queen Canal Cruise are popular things to do here.

Islamorada

Islamorada is the halfway point between Miami and Key West. Here you can visit Indian Key Historic State Park and feed giant tarpons.

Marathon

Marathon sits in the heart of Florida Keys. Sombrero Beach that’s located in Marathon is one of the best beaches in the Keys. And here you can also visit Florida Keys Turtle Hospital.

Lower Keys

Lower Keys before Key West is home to the Key deer. In the National Key Deer Refuge the tiniest member of the North American white-tailed deer family lives. The area is also home to Bahia Honda State Park and its famous beach.

Road to  Key West
You can make a road trip to Key West or go by plane or boat.

Key West guide FAQ

Here you find the answers to some frequently asked questions about visiting Key West.

Is Key West worth visiting?

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!

How many days do I need in Key West?

Key West is such a small and compact place that you could explore the main attractions on the island in 2-3 days without hurrying around too much. However, to fully unwind during your stay more days are recommended. Also, add time if you want to do activities on the water such as a day trip to Dry Tortugas.

Can you see Cuba from Key West?

You can’t see Cuba from Key West. Cuba is only about 90 miles (145 km) away from Key West, but that’s too far away to be able to see it. If you visit the Key West Lighthouse you can’t even see half that distance even on a clear day.

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