One Day in Key West Itinerary – Top things to do in Key West, Florida

Ah, good old Florida. A great place to visit if you want to have some serious fun, enjoy the beaches, explore different cultures and watch beautiful sunsets. Yes, sunsets. For that, head to Key West, an island off the state’s southernmost tip. Not only will you enjoy some spectacular colors in the sky every day at dusk, perfect for spending some time with your significant other, but you will also have a great chance to do some serious exploring and see firsthand why so many famous people were so delighted with this place. Spend one day in Key West if at all possible and it will pay off immensely.

One Day In Key West Itinerary, Florida

What’s the best time to visit Key West?

Given its location, Key West has a tropical climate, so it’s perfectly suitable for visits all year round. Some things have to be kept in mind, however. The dry season lasts from November to April, so this may be a better time to visit. The wet season is between May and October (especially from August), so if humidity poses a problem for you, you may want to skip that. Hurricanes also hit the island during this period, although that is actually quite rare.

Fantasy Fest, Key West
Car at the Fantasy Fest, Key West, Author: Michel Curi, Source: Flickr

As for the events you can enjoy and things to do in Key West, they come in all shapes and sizes, so you are guaranteed to have an excellent time while here. Fantasy Fest is one of the bigger events, though, held in October, but the Conch Shell Blowing Contest in March sounds like a lot of fun, too. Hemingway Days in July honor this famous writer, and there are plenty of other interesting events all over the Florida Keys archipelago.

Hemingway Days in July, Key West
Hemingway Days in July, Key West, Author: Erin Borrini, Source: Flickr

A few facts about Key West

Key West is a city and an island in the Florida Keys archipelago. It is actually the southernmost city of the United States and the end of U.S. Route 1, which is the longest road in the country spanning from north to south. With Cuba being less than 100 miles away, there is a strong Cuban influence in the city. Fun fact, the distance between Key West and Havana is shorter than the distance from Key West to Miami.

Southernmost Point of the USA, Key West
Southernmost Point of the USA, Key West

Ernest Hemingway and Tennessee Williams both had houses in Key West, with the former actually being quite prolific while in town. Hemingway wrote or worked on several of his works while living here, the most notable of which is probably For Whom the Bell Tolls. The theater in Key West is named after Tennessee Williams.

Tennessee Williams, Truman Copote, Tom McGuane and James Kirkwood in the 1970s. From the Key West Art and Historical Society.

One Day in Key West Itinerary

Follow this guide and make the most of your trip even if you’re short on time. These are the top sights and things to do and see during your one day in Key West.

Start your day in the Historic Seaport

Historic Seaport in Key West has been functioning for more than 200 years. However, since it doesn’t get too crowded here, it’s a great place to get yourself a cup of Cuban coffee and simply enjoy the morning a bit. The boardwalk is a lovely way to start making your way towards the city center (i.e. Duval Street), but not until you check out all the galleries, shops and all other things to do here. It’s the best free thing to do in all of Key West.

Duval Street, Key West
Duval Street, Key West, Author: Lucas Klappas, Source: Flickr

Go to Ernest Hemingway Home and Museum

This literary behemoth lived and worked in Key West for ten years, so it’d be a shame to skip Ernest Hemingway Home and Museum while in town. This beautiful house has plenty of Hemingway’s personal artifacts, and there are guided tours that will tell you all about this exceptional writer every fifteen minutes. Don’t be surprised by all the cats here – they all have six toes and are descendants from Hemingway’s own cat Snow White. For just 14$ per adult ticket, this place is very much worth a visit.

Ernest Hemingway House, Key West
Ernest Hemingway House, Key West, Author: Aan Kasman, Source: Flickr

Enjoy a delicious lunch

Given the island’s location, you know there will be some good food to eat here. Cuba is close, so why not go for some Cuban food? El Siboney Restaurant serves some good grub for some really affordable prices and you can’t go wrong with it. Blue Heaven is another great restaurant famous for its Key Lime Pie, but you may have to wait for your table a bit here (which is really worth it because the food is FANTASTIC), so maybe make a reservation first. Fish from the local waters is especially good. Finally, Banana Cafe and Caroline’s Cafe are also excellent places to get good food at reasonable prices.

Lobster Bbedict at Blue Heaven, Key West
Lobster Bbedict at Blue Heaven, Key West, Author: Sam Howzit, Source: Flickr

Relax at Key West Butterfly and Nature Conservatory

What to do after lunch? Near the southern end of Duval Street, you will find Key West Butterfly and Nature Conservatory. It’s a lovely place for a walk after lunch with an incredible amount of beautiful butterflies. Not only that, but you can see a whole lot of birds here, including flamingos. Wow! So, if you have kids along with you this is something they’ll love, but even adults can relax and enjoy some peace and quiet here. Oh, and they also have a great little gift shop with loads of great souvenirs.

Iguana at the Nature Conservatory, Key West
Iguana at the Nature Conservatory, Key West, Author: Cayobo, Source: Flickr

Tour Fort Zachary Taylor

Fort Zachary Taylor was built in mid-19th century and is a great place to visit for history buffs, especially because of the canons from the Civil War. You can enter with a car, plus the tickets are really not that expensive, so it’s well worth a visit. You can tour the fort on your own and then hit the beautiful beach nearby to simply chill out and just enjoy the fact that you’re here. A great way to learn about the island’s history a bit and then simply relax.

A stack of Cannonballs at the Fort Zachary Taylor, Key West
A stack of Cannonballs at the Fort Zachary Taylor, Key West, Author: Haydn Blackey, Source: Flickr

Witness the sunset at Mallory Square

Once you’re done with the fort, head to Mallory Square. There is plenty to see here, as many street artists will compete for your attention, and with plenty of shops, bars and restaurants you’ll never get bored. But the main attraction here is the sunset which is nothing short of awe-inspiring. The sky turns bright orange with black silhouettes of ships dotting the sea. Mind you, there will be a lot of people here, but a sunset here is among the best things to do during your one day in Key West.

Mallory Square Sunset, Key West
Mallory Square Sunset, Key West, Author: Ed Schipul, Source: Flickr

Find a place to party on Duval Street

You’re not here to go to bed early, are you? Get out there in the evening and head to Duval Street, the busiest street in town. It feels like the whole world is here, with people from all so many different countries having a great time. There are dozens of bars, restaurants and plenty of live music, so you won’t have to worry about what to do in Key West in the evening. Sloppy Joe’s Bar seems to be one of the most popular places around, but the selection is huge and if you’re in the mood for bar hopping, go for it! Captain Tony’s Saloon, Kevin’s Irish Bar… Get yourself a nice drink (the cocktails are a great choice) and enjoy the hot tropical night.

Beer and Rum Punch at Captain Tony's Saloon, Key West
Beer and Rum Punch at Captain Tony’s Saloon, Key West, Author: Sam Howzit, Source: Flickr

Visit the smallest bar in Key West

Appropriately named Smallest Bar, this is a great place to visit, especially if you don’t know what to do after exploring Duval Street. Located at its northern end, visiting this is one of the best things to do in Key West at night if you want a good laugh with your friends: the bar only has four seats and a chatty bartender, so you should feel quite pleasant and cozy. It’s also a great photo op which will certainly make for a good story when you get back from your trip. Enjoy!

Smallest Bar, Key West
Smallest Bar, Key West, Author: Stig Nygaard, Source: Flickr

Where to stay in Key West?

Simonton Court Historic Inn & Cottages, Key West

Simonton Court Historic Inn and Cottages

320 Simonton Street, Downtown Key West, Key West, FL 33040

Simonton Court Historic Inn and Cottages is one of the best accommodations in Key West. Its charming antique style sets the mood perfectly, but the hotel has every modern amenity you could wish for. With four outdoor pools and a beautiful garden you will be able to enjoy the tropical sun to the fullest, and there are plenty of sights, bars and other interesting places nearby.

BOOK A ROOM HERE

Truman Hotel, Key West

Truman Hotel

611 Truman Avenue, Downtown Key West, Key West, FL 33040

An outdoor pool with magnificent palm trees, great location and a few rooms with balconies are the highlights of Truman Hotel. If you stay here, you will be close to Duval Street and the best of Key West’s nightlife and will be able to enjoy rooms with wooden floors. Great staff only adds to the overall impression, so you really can’t go wrong if you choose to book a room here.

BOOK A ROOM HERE

Douglas House, Key West

Douglas House

419 Amelia Street, Downtown Key West, Key West, FL 33040

If you want to be right in the middle of things and are interested in Key West’s nightlife, Douglas House is the perfect place to stay. The inn is located on Duval Street, but on its more peaceful part, so you don’t have to worry about getting enough sleep. It has an outdoor pool, a wonderful garden and is close to many interesting sights. The rooms are very comfortable and well equipped,with very interesting design, but be aware that this place is for adults only.

BOOK A ROOM HERE

Eden House, Key West

Eden House Key West

1015 Fleming Street, Downtown Key West, Key West, FL 33040

Eden House Key West is a hotel that has been operating all the way since 1975. It has a great location, close to the Duval Street and in the old town. It has a pool and even hammocks, so it’s a great place to spend a lazy afternoon. The interior is absolutely lovely and very comfortable, so you will enjoy staying in the rooms which all have all the necessary amenities. The whole building is wonderfully designed, but do be aware that smoking is not allowed.

BOOK A ROOM HERE

Day trips from Key West

While the island really is magical, if you’re spending more than one day in Key West there may be some great opportunities for a day trip from the city. Some destinations are very much worthy of consideration, so here’s what to do if you want to head out of town.

Dry Tortugas National Park

There is some truly fascinating nature all around the island, and no place shows that better than Dry Tortugas National Park. Not only will you enjoy the beauty of the tropical sea in the Gulf of Mexico, but once you get to the park you will be able to jump in the water and enjoy snorkeling around coral reefs. You could even see sea turtles and dolphins, but don’t forget to explore Fort Jefferson when you have the time. This day trip from Key West is something you’ll never forget.

Miami

Why not spend one day in Miami if you have the time? Sure, it’s not exactly close with about three and a half hours’ ride between the two cities, but if you have two drivers who can switch this is a great idea. Miami is a fantastic city, with great beaches, incredible nightlife, celebrity houses and a big Cuban community, but the drive itself is incredibly beautiful thanks to the Overseas Highway where you are literally driving above the ocean.

Sail around Key West

The waters around here are perfect for sailing. Not to mention they’re teeming with life. So why not get yourself a boat and go exploring? You can jump in and snorkel a bit to explore some of the shipwrecks, enjoy the beauty of the coral reefs and watch wild dolphins play all around you. Or you can just relax on the boat in shade, pour yourself a nice cool drink and really soak in that tropical atmosphere, the choice is yours!

Dolphin Research Center

Among the most popular day trips from Key West is a visit to the Dolphin Research Center. You will travel the Overseas Highway and enjoy spectacular views, and then see how dolphins that cannot survive in the wild are being taken care of. Feed them, learn all about them and see them up close and personal. After that, if you have the time, head to National Key Deer Refuge for more incredible animals, including alligators!

Extra tips for visiting Key West

  • While this is a really wonderful place to visit and there are parties and celebrations all the time, remember that going around with a bottle of beer (or any other alcoholic beverage) around here is illegal and will get you fined. Drink inside.
  • You may be surprised by the chickens running around town. They are actually protected by law, so don’t do anything stupid to them. Furthermore, the iguanas around here will swarm you in minutes if they see you’re feeding one of them. Don’t.
  • Obviously, like the rest of Florida, Key West is hot. Therefore, it would be a good idea to always have some sort of refreshment with you. Carry a bottle with you, don’t leave kids in cars and generally take the heat seriously.

If you have any other propositions for this One Day in Key West Itinerary, feel free to share it in the comments below!

Logistical Tips and Tricks

Organize your trip in five easy steps!

BOOK A FLIGHT!

Obviously, if you’re going on a trip somewhere far a way, you’ll need to book a flight. There is absolutely no need to worry about this, though, because with Skyscanner, you will be able to find a cheap flight anywhere in the world. And their website is extremely easy to use, so you will have your seat on a plane in no time at all!

BOOK A ROOM!

To easily find the best possible room in the city you’re visiting, just head to Booking.com. They have quite literally thousands of options, a reliable rating system and will always get you a great deal. On top of that, you can learn a lot from the comments people leave there, too. No matter if you’re looking for an apartment or an elite hotel, you’ll find what you need here.

GET A CAR!

If you want the ultimate sense of freedom while on your trip, a car is a must. Fortunately, there is a simple way to get one – just visit Booking’s Rentalcars and they’ll have your vehicle ready in a jiffy. Now you’ll be able to explore the new city thoroughly and, who knows, maybe even make a trip outside it.

INSURE YOURSELF FOR PEACE OF MIND!

Accidents, mishaps and other troubles happen to everyone. The key is to be prepared. That’s why getting a travel insurance is such a great idea: it can help you deal with any health issues, theft and even cancelled flights. World Nomads know full well about the problems that can arise on a trip because they are passionate travelers themselves. That’s why they can offer you the very best deals.

FIND SOMEONE TO HELP YOU GET AROUND!

Want to have some company as soon as you land? Through Welcomepickups.com, you can find a local to meet you at the airport and help you find your way around the new city. They can also set things up for you, give you some useful tips and be helpful in general. The whole project is a great idea and very well executed, so do go and see how these people can make your trip a more pleasant one.

Anca One Day Itinerary
Anca B.
Travel writer at

Anca is a travel writer and the founder of One Day Itinerary - the biggest collection of travel itineraries for those who are time-limited or just want to maximize their time while traveling. Although she easily becomes homesick for Croatia, she thinks travel is essential to her happiness. She has traveled to more countries than she is years old and doesn’t plan on changing that fact. In her travel guides she aims to inspire people to travel whenever they have a spare day (or two).

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