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.
Plan your trip to Key West
1. What’s the best time to visit Key West?
2. A few facts about Key West
3. One Day in Key West Itinerary
3.1. Start your day in the Historic Seaport
3.2. Go to Ernest Hemingway Home and Museum
3.3. Enjoy a delicious lunch
3.4. Relax at Key West Butterfly and Nature Conservatory
3.5. Tour Fort Zachary Taylor
3.6. Witness the sunset at Mallory Square
3.7. Find a place to party on Duval Street
3.8. Visit the smallest bar in Key West
4. Where to stay in Key West?
5. Day trips from Key West
6. Extra tips for visiting Key West
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.
As for the events, 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.
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, Key West is closer to Havana than it is to Miami.
Ernest Hemingway and Tennessee Williams both had houses in this town, 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.
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.
At the end of the day, be sure to book and experience romantic sunset on the deck of a sailboat!
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.
Go to Ernest Hemingway Home and Museum
This literary behemoth lived and worked here 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.
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.
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.
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.
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.
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.
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!
Where to stay in 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.
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.
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.
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.
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.
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.
Just sail around
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.
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Anca B.
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).