Colorful coral reefs. Six-toed cats. A haunted doll. Key West, Florida may be one of the most unique places in America: roosters roam the streets, drag queens rule the nightlife, and Cuba’s close proximity colors its history. The entire island is a colorful, tropical feast for the senses. Is this paradise? I thought it would be less …. weird?
To really appreciate Key West in all of its quirky glory, you also have to get to know its long history of pirates, bootleggers, and nonconformists; its resident ghosts and grave-digging iguanas; and the resident animals who call it home.
So, we tapped an insider to give us the scoop on Key West’s most strange and wonderful places to help us out. Here’s everything you need to know to plan your trip, and all the quirkiest, best things to do in Key West! Take it away, Haylee!
Table of Contents
Psst: Planning a trip to Florida? Check out our travel guides to other places nearby:
- How to Do Disney (by a Former Cast Member)
- The 10 Best Weekend Getaways in Florida (and Over 60 Activities!)
- The Perfect 3-Day New Orleans Itinerary
- 38 Enchanting Things to Do in Savannah, Georgia
Looking for more USA inspiration? We have a MASSIVE travel guide for all our favorite places in the US and handy advice, packing tips and travel guides. Click the link below to download!
Key West FAQ’s
Here are a few helpful things to know while planning your trip to Key West:
- When is the best time to visit Key West? The best time to visit Key West is in the spring, between March and May. By this time of year, it will be about 80-85 degrees during the day and before hurricane season begins, so you won’t have to worry as much about random showers interrupting your day. The peak winter tourist season will also have ended, so the island will be less crowded and places to stay will typically be cheaper.
- Should I rent a car? I wouldn’t recommend it. The island is so small you can Uber/Lyft to the place you’re staying, then walk or bike to nearly everything else you need to. If you do choose to rent a car, I have to warn you, as a terrible driver myself, I would NEVER drive in Key West. The roads are super busy, not only with cars, but with mopeds and bicycles. If you do choose to drive, bring change: you’ll be parking on the street most of the time and most of the meters only take exact change. The one benefit of renting a car is that you can take a scenic drive down the Overseas Highway, where you can stop and take pictures of the ocean only a few feet away from the road.
- How do I get to Key West? You can fly directly into the Key West International Airport and take a Lyft to your accommodation. Although I hate most airports, I just have to love this one. It’s just one room, with two luggage claims, and one security guard who just looks at you and nods. Yup, this airport is just as relaxed as the rest of the island. And if you want to get started with relaxation the instant you get on the island, there is a tiki bar. That’s the layout: tiki bar, security guard, two luggage claims, and a bathroom. It’s amazing.
- How do I get around in Key West? You can walk and bike everywhere! Key West is a compact island, and most of the places you’ll want to go to will be no more than a 5-15 minute walk or short bike ride, depending on where you’re staying (more on that below).
Things To Know Before Going To Key West
I’m pretty sure that thanks to all the ridiculous news stories that come from Florida – from Florida Man memes to a woman whose pet gator rides a motorcycle and wears clothes – the rest of the country thinks that Florida (at least outside of Disney World) is a weird mystery land.
Well, I’m not going to argue with that. But if you really want Florida weirdness, you have to go to Key West.
Key West is Florida’s quirky little island paradise. It has a long history of military involvement due to its strategic location, as well as being considered a safe place for LGBTQ+ people. While you won’t find Mickey Mouse here, there are plenty of drag shows, a living doll, and a lot of cats.
There are a few more things you need to know about Key West before you go (that may or may not actually help you plan your trip):
- There are a lot of chickens in Key West. You are going to hear and see more chickens than you ever have before in your life here. Cockfighting was popular in Key West in the 1800s and 1900s, until it was banned. When that happened, all the chickens were suddenly released to the island. No one made an effort to get rid of them, and now they are welcome on the island as friendly wildlife. So don’t touch or feed them: they are wild!
- Key West is home to a lot of six-toed cats. I blame Ernest Hemingway, who lived there and had a 6-toed cat, and now his historic house is home to 60 of them! While most of these cats are friendly, please don’t try to pet them. They are still wild animals and as a general rule of thumb, don’t try to pet wild animals.
- … and also iguanas. The green iguanas are an invasive species believed to be stowaways on ships from Central and South America, and they’re considered quite a local nuisance (apparently, they like to dig up graves). That said, leave eradication to the professionals. Iguanas are amazing, beautiful animals and you might think it’s ok to pick them up for a picture – but it is not ok. It stresses the animal, and they could seriously hurt you with their claws! For your own safety, don’t touch them.
- Key West is an LGBTQ+-friendly place! In the 70s-90s, Key West was considered a safe place for young LGBTQ+ people to go if they needed shelter. Today, Key West’s culture is largely shaped by LGBTQ+ traditions and events, and you’ll see Pride flags flying all over the island year-round! (The subtext here is that if any of that makes you feel uncomfortable, maybe just stay home and do some internal reflection.)
- Florida has a large homeless population, especially on Key West. Going to the Keys, you will see poverty right next to very rich people, and if you have some extra change or food, it won’t go unappreciated by them. Please keep in mind that the folks experiencing homelessness are our neighbors, and not a blight or an eyesore. Some of the folks that you will see may also be struggling with mental illnesses. Although this can be startling, remember that these people are in far more danger than you are, and are unlikely to harm you in any way. Homelessness is traumatic, particularly for the mentally ill, whose conditions can be exacerbated by the stress of homelessness. Please consider helping the local homeless community by donating to the Florida Keys Outreach Coalition. You can make a financial donation online or donate clothing, non-perishable food, and unopened hygiene items at Loaves & Fish Food Pantry at 2221 Patterson Ave in Key West.
- Key West once seceded from the United States and declared itself the Conch Republic. In 1982, the U.S government set up a roadblock intended to capture the many immigrants coming from Cuba, just 90 miles away. It also inconvenienced tourists, who are the financial backbone of the local economy. Well, Key West is not a place for passive people, and that didn’t sit well with them. So Key West’s then-mayor declared himself Prime Minister of the Conch Republic and immediately declared war on the United States of America by symbolically halving a stale loaf of Cuban bread over the head of a person wearing a U.S. Navy costume. He surrendered one minute later, but that wasn’t the end of the Conch Republic’s battles with the US government: in the mid-90s, the Republic attacked a Coast Guard ship with water balloons, conch fritters, and stale bread. They dispersed when the Coast Guard sprayed a hose back at them. Wikipedia has a short run-down on the entire tongue-in-cheek-but-also-not-really history!
- Take the trolley! If you want a quick way around town AND to get some history while you’re at it, use the Hop-On Hop-Off Trolley Tour, which goes to 13 spots around town and is a fun, educational way to spend a day. The trolley also doubles as a ghost tour late at night – more about Key West’s resident ghosts later.
- Pack a raincoat. Be aware of the fact that it can rain at literally any minute, especially in the mid-summer to early fall season. And when it rains, it pours. A mini-rainstorm can come out of nowhere and disappear 15 minutes later. If you hate rain, my best advice is to either learn to love it, or pray to the rain gods that you’ll be blessed enough to not experience any rain. If those options don’t work, just bring a poncho.
- Key West beaches are actually pretty rocky. Despite its picture-perfect appearance in most photos, a lot of spots on the island are pretty rocky at the shore, then gradually the rocks give way to a sandy bottom. These can be a pain to walk over to get to the sandy part of the ocean, so water shoes or Teva sandals are recommended.
The Best Things To Do In Key West
Go Snorkeling in a Coral Reef
One of the most fun ways to enjoy the local environment is snorkeling! Folks, I am OBSESSED with snorkeling. Coral reefs are a whole new world to explore: underneath the blue water there is an abundance of fish and neon-colored coral to see. With all the life here, you can stay in the water for hours and still find yourself noticing new details, with sea critters swimming every which way.
But before you go snorkeling, a few crucial notes: always use the buddy system, don’t touch the coral -for your safety as well as its – and make sure you’re wearing reef-safe sunscreen, NOT regular sunscreen.
If you’re not confident about your snorkeling skills or you’ve never gone before, we included a few guided tour options.
What wildlife can I see while snorkeling?
Key West has a lot of big, beautiful fish! Some of the ones to keep an eye out for while snorkeling are:
- Parrotfish: Key West has an abundance of Parrotfish! Rainbow Parrotfish are especially eye-catching. If you go snorkeling and see these fish near coral, stop swimming for a second and listen – Parrotfish keep coral clean by using their teeth to scrape them, and you can actually hear this in the water.
- Manatees: Manatees are super cool to see in the water! You are more likely to see them in areas with seagrass rather than a coral reef, since they graze on seagrass. If you see a manatee, consider yourself lucky because you just saw a mermaid. It’s thought that sailors started the legend of mermaids by mistaking manatees for humans with tails from afar.
- Dolphins: The Keys are filled with bottlenose dolphins, so the likelihood of you seeing a few jumping and playing in the water is pretty high. Dolphins in Florida oftentimes give birth in spring and summer, so if you visit during these times try to keep an eye out for any small calves swimming right under their mothers. Certain tours, like this one, will take you to specific spots where bottlenose dolphins tend to hang out!
- Stingrays: To see stingrays in Key West, you’ll have to really keep an eye out. Stingrays tend to lay in the sand and rest so you might swim right over one without even noticing it! The easiest way to spot a stingray in sand is by looking for a sandy rock that appears to have eyes, and sometimes a tail if the particular stingray is feeling too lazy to bury itself in all the way. However, if a Giant Manta Ray passes by you, you definitely won’t be able to miss it. When these rays are born, they’re already six feet wide, and an adult can soar through the water with lengths of 24 feet.
- Sea Turtles: If you’re really lucky, you might see a sea turtle! Several species live in the Keys. The most common ones are Loggerheads and Green sea turtles. Sea turtles are most often found floating along in the currents, looking more relaxed than any beach-goer.
- Sharks: Most sharks here aren’t particularly dangerous species- nurse, lemon, and sandbar sharks are the most common. I actually saw a sandbar shark one time while snorkeling! There has never been a fatal shark attack in the Keys- just don’t be the first by trying to pet one, as cute as they are.
Where can I go snorkeling in Key West?
Key West is surrounded by reefs, but they’re a little ways offshore – the easiest way to get to them is by boat. That said, there are a few great places around the island to snorkel and see some of these ocean creatures in their native habitats:
- Fort Zachary Taylor State Park: The only reef I know of that you can reasonably swim to is the one in Fort Zachary Taylor. The admission for pedestrians is $2.50 and you can spend the entire day there- there’s not only swimming, but the park is known for having many tropical species of birds you can see. These reefs may be your best chance to catch a glimpse at the elusive sea turtle as well! Since you will be on your own in this reef, make sure you bring your own snorkeling gear or rent one at the park (either way, pack anti-fog spray).
- Dry Tortugas National Park: Thanks to efforts by the local government to keep the island reefs alive, this reef is healthy and happy – so if you want to see one that is really thriving this is the place to go. It’s colorful, with a variety of coral species and plenty of fish to see! Dry Tortugas is also home to historic Fort Jefferson. Note that in order to get to Dry Tortugas you have to take a boat and purchase an entrance fee to the National Park. This day trip includes round trip ferry service, snorkel gear, breakfast and lunch, and an optional guided historic tour.
- Book a Snorkeling Tour: The good thing about snorkel tours is that they will provide snorkeling gear and help from the guides, along with the guide’s knowledge on the area and local animals. This snorkel tour takes you out to the Great Florida Reef – the only living coral barrier reef in the United States and the third-largest in the world – on a 69-foot catamaran for 3 hours of fun in the water. Or, take a gamble on the Island Adventure Eco Tour: each tour is different and the snorkeling location varies depending on the weather and what animals are swimming around where! You can also choose to end your afternoon with kayaking at sunset – what a perfect Key West day!
Check Out Key West’s Historical Homes
Key West’s history has shaped it into the quirky destination it is today, and is reflected in its many historical homes and local legends. Understanding Key West’s history makes wandering its colorful streets all the more enjoyable!
Before the island’s name was anglicized, to Key West, it was called Cayo Hueso, or Bone Island, by the Spanish who charted the island in 1513 when they were off looking for the Fountain of Youth.
Before the arrival of the Spanish, the Florida Keys, including Key West, were inhabited by the Calusa and Tequesta peoples, who were known as skilled fishermen and expert sailors. Sadly, both the Calusa and Tequesta people were decimated by the late 1700s due to European diseases and conflicts.
The island was an important burial ground for the Calusa people and the Spanish named the island after the many human bones they saw, but there is some debate that the name could also be attributed to the limestone rocks and reef formations that also looked like giant sun-bleached bones.
While Key West’s waters may have hosted pirates from time to time, it wasn’t until the early 1800s that there were permanent Spanish residents of the island. Eventually, Spain transferred control of the island to the United States in 1821, but it’s easy to see the influence of Spain, and nearby Cuba on the island to this day, especially in Key West’s historical homes and landmarks.
Here are some of the most famous historical spots you can check out on the island:
Hemingway House & Museum
Hemingway House & Museum is in Old Town Key West, and this yellow, airy, many-windowed home is in the French Colonial style with many art deco accents on the inside. This is a really big attraction on Key West for good reason – Hemingway was a prolific writer during the 1920s and 30s, and he wrote two of his most famous books in this very house: A Farewell To Arms and To Have and Have Not.
Ernest Hemingway lived in Key West for years, making the island his permanent place of residence in the 1930s, and is the man who I have decided to fully blame for all the cats on the island (according to the official website, more than forty cats, who are all named, live here).
On a personal note, did anyone else have an English teacher that was WAY too into Hemingway? Or was it just me??
Custom House/Key West Museum of Art & History
The second house you should see is the iconic red Custom House, just off of Mallory Square in one of the main parts of town. The house was built in the 1800s and was the Customs building in Key West. During the Spanish-American War, the Custom House was home to the U.S. Navy Department’s board of inquiry into the sinking of the USS Maine in Havana, which eventually led to America formally declaring war on Spain.
Today, the Custom House is the site for the Key West Museum of Art & History. Many of its permanent exhibitions relate to the Spanish-America War, the Cuban Missile Crisis and Key West’s role in those historic events. Since there is a naval base on the island, radar and intelligence stations were set up on Key West during the 1960s. During the blockade of Cuba, reconnaissance planes were housed here to easily fly over Cuba and monitor for the presence of nuclear weapons.
For true crime lovers like me, there are also a few darker exhibits chronicling some of the tales that could be straight out of a Gothic novel. One of these exhibits is about a “love story” (psyche, it was actually horrifying and creepy) between a local German doctor and his patient, who died of Tuberculosis.
Instead of accepting her death – and the fact that she just wasn’t into him – homeboy stole her corpse, slapped some makeup on it, and lived with it for SEVEN YEARS until he was caught (AHHHHH). You can learn all about the creepy story of Carl Tanzler at the museum.
Audubon House Museum & Tropical Gardens
Now known as the Audubon House, this home was originally owned by John Geiger in the 1840s, a man who profited off of shipwrecks and enslaved human beings. In the 1800s, the wrecking industry was big in Key West because of the treacherous nearby reefs, and men like Geiger – uh, government-sanctioned thieves, I guess? – would take and resell valuables from the ships. He became one of the richest men on the island.
During this time, anti-abolitionist, white supremacist, and bird enthusiast John Aubudon visited the home and was fascinated by its gardens, and today is thought to have found inspiration from the birds flitting about the colorful foliage. He later rose to fame as, more or less, “that guy who pants birds.”
Many of his bird paintings line the house to this day, and when the museum was opened in 1960 complete with his artwork, it was named after him. You can visit the museum to get an idea of how wealthy people once lived in Key West.
- Editor’s Note: Unfortunately, it seems that the museum has chosen to depict a one-sided narrative regarding the wealthy former owners of the home and the famous painter it’s now named after, rather than tackling the hard-to-swallow truth about how their wealth was made by possible by enslaved men and women. It’s high time for museums like this one to rework their narratives to be more honest, and for us as tourists to withhold our financial support until that shift takes place. For historical accuracy about the ugly reality of wealthy life in the Antebellum south, we recommend visiting the Owens-Thomas House in Savannah, Georgia – read our Savannah post to find out why – or one of these historic house museums instead.
Meet Key West’s Resident Animals
Key West has no shortage of tropical birds, lizards, and bugs on the island – not to mention the roosters and cats, which aren’t tropical at all, but are very much a part of Key West life.
If you want to get to know a few of Key West’s resident animals, there are a lot of great places to go to do exactly that:
This park has one of the nicest sandy beaches on the island! For $2.50, you can spend the entire day swimming, snorkeling and looking for the many tropical species of birds the park is known for.
You’ll likely see herons and cormorants if you keep an eye out and look around less-populated mangrove areas, where these birds like to wade to catch fish. If you’re really lucky, you might even see a sea turtle out by the reefs, which are accessible from the shore.
The birds in Key West are all beautiful, but my favorite is the Roseate Spoonbill. (Fun Fact: I thought it was the Rose Spoonbill until I looked it up to fact-check myself, so maybe I shouldn’t call it my favorite.) If you see a pink bird that looks like a small flamingo, that’s your spoonbill!
In this unique sanctuary, you’ll meet rescued abandaned, mistreated and unwanted macaws, cockatoos and parrots rescued lovingly by Nancy Forrester, an environmental activist and educator. You’ll learn all about these intelligent, social birds and can even hold them and pet them, as long as you’re gentle.
Also, Nancy is an all-faith wedding officiant, and she’ll use her birds as official witnesses. I really want to see a wedding here, I think it’d be awesome.
That said: the worst part about this place is that the birds might POOP ON YOUR VERY NICE AND NEW SHIRT YOU GOT FOR THE TRIP. Be smarter than me. Don’t wear nice clothes to play with animals who will poop on you without warning!
The conservatory feels like paradise, filled with colorful butterflies and birds, tropical flowers and waterfalls. There are about 50 species of butterflies here. Perch on a butterfly-shaped bench and sit and watch them snacking on fruit – if you’re lucky, one might even land on you to say hello.
You’ll also see also flamingoes, turacos, lizards, and other brightly colored birds that I don’t know the names of (just know they’re all tropical and very friendly). On your way out, pick up a glass-sculpted butterfly hand-crafted by the conservatory’s owner in the gift shop as a souvenir!
Just roaming on the island is a great way to see plenty of cats and chickens in Key West. As I mentioned earlier, it’s thought that Ernest Hemingway is the first person who spurred the cat boom to Key West since many of them have six toes rather than the normal five, just like his cat. (This is called polydactylism in cats.)
The cats of Key West especially love to laze around under the shady canopies of the palm trees. Many of the cats can also be seen near the docks, watching small fish swim around in the ocean beneath them. I’ve yet to see a cat jump in to grab one, but I’m sure they want to.
The chickens are here because in the 1800s, cockfighting was popular on the island until it was banned and all of these chickens were abandoned on the island. Despite being descended from hardened fighting chickens, the chickens seem to get along pretty well with the cats. I would have guessed the cats would chase the chickens, but there are never any chicken-cat territory wars or chases.
In springtime, you’ll see a lot of adorable baby chickens running around on the island! I love seeing a chicken walk out with one or two babies behind her, then a few seconds later three more babies pop out of the bushes and walk in a line behind her across the road.
- Editor’s Note: If you happen to get a photo of a 6-toed cat, a chicken, and an iguana all in one shot, you just won Key West bingo! And please share your photo to us in the comments because we’d very much like to see it.
Visit Mallory Square
Mallory Square is filled with local shops and stalls selling souvenirs alongside handcrafted goods and locally made art (plus a few chain stores and tourist traps thrown in the mix). Shopping can be a great way to support local businesses and peek at local curiosities.
Here are the top things to do in Mallory Square:
- Buy a Sponge: Key West has a large sponge population. Sponges, in their natural habitat, quickly regrow when pieces are taken off. The sponging industry was once a major source of income for Key West. – you can learn more about that history at the Sponge Market. But historically, sponges were harvested using a hooking technique that rips off most of a sponge, leaving the sponges with less than a 50% chance of survival. Today, they’re harvested through cutting techniques which only takes a bit off at a time so the sponge can regrow. Due to this, they can be a bit pricey, but they last for a really long time and work as natural exfoliants when you shower. When you go snorkeling in the natural reefs around Key West, keep an eye out for sponges! You can see them in shallow waters. But don’t touch them or take them home with you – purchase a sustainably harvested one at a local shop instead.
- Try some Rum: On Mallory Square, Key West’s First Legal Rum Distillery (self-proclaimed the official rum of the Conch Republic!) has plenty of rum to freely sample and buy. The distillery is located in an old turn-of-the-century building that used to serve as a saloon in 1900 – you can take a free private tour of the distillery to learn more!
- Get Your Fill of Key Lime: At Kermit’s Key West Lime Shoppe, you can get your fill of Key Lime anything. There’s way more than pie here- sample the key lime salsa and lime shnappes, then get a shirt on your way out.
- Check out some Life-Size Bronze Sculptures: In Mallory Square, in front of the aforementioned Custom House, you’ll notice a lot of bronze statues. Seward Johnson was a sculptor who donated his creations to various museums around the country – and the statues are circulated among different museums every few years.
Editor’s Note: Another popular local landmark is the Shell Warehouse, but we don’t recommend patronizing it because of the damage that the demand for seashell souvenirs cause to marine environments – read more here.
Take A Photo At One Of The Key’s Unique Spots
Since Key West has such an old history, there are plenty of special places to visit and take unique photos as a memento of your trip!
Not only can you check out some excellent views, but you can also visit the southernmost point of the US. Here are some of the best photo spots in Key West:
- Key West Lighthouse: This lighthouse is exactly what you picture when you think of a classic lighthouse: tall, white, and stately. Built in the mid-1800s, you can’t miss its bleached white exterior against the green and blue landscape. Step inside and you can learn a little about the lighthouse’s female keeper, Barbara Mabrity, and how lighthouse keeper was one of the first non-clerical government jobs that were open to women. Next, climb the 88 steps to the top of the tower to see sweeping views of the Gulf of Mexico and the Atlantic Ocean in panoramic glory. This lighthouse is very well-maintained, and I think it’s one of the best places to take pictures. Sadly for me, those photos are wasted, because the only ones I have are super blurry selfies of me in middle school with a weird side part and no one is ever allowed to see that again.
- Bonus Tip: At the top of the tower, look for yachts on the water and remember the names of them so you can look them up – sometimes famous people cruise by!
- Southernmost Point Buoy: Located at (you guessed it) the southernmost point of the island, near the US Naval Base, this is essentially just a painted buoy statute marking that it’s the southernmost point of the continental United States. (Only 90 miles to Cuba!) It used to be marked by a small sign, but in 1983, the city built this concrete buoy. What’s really impressive about this buoy is that it’s survived several hurricanes (including the devastating Hurricane Irma) and has only gotten a bit scratched. Since this is such an iconic symbol of Key West, the line to take a picture of it is usually ridiculously long at most times during the day and, in my opinion, not worth it. If you really want to get a picture without waiting in line, go early in the morning or really late at night.
- Mile Marker 0: Mile Marker 0 is a neat little place to take a photo! You’ve reached the end of the road (literally), and have found what comes afterward: Paradise. I don’t think too many people know about this sign here because I’ve never seen it crowded. Mile Marker 0 is a street down from Duval, on Whitehead, and is worth the short walk to get a quick photo opportunity.
- Overseas Highway: If you are driving down from the mainland to Key West, you will be driving down the Overseas Highway. The highway will take you well above the crystal clear waters of the Keys, and you can see reefs from the bridge. Other parts of the highway will take you only feet from the water, and you can pull off and take pictures right at the shore of the mangroves. The unique part about taking a photo on the highway is that you can capture the string of islands from the beach next to the highway.
- Duval at Night: Duval at night time is lit up by all the bars, shops, and partiers. If you want to take photos with a lot going on in them, walk around Duval at night with a ready camera. Who knows what will walk by in front of you? A drag queen, a man wearing a sign proclaiming the end of the world (speaking from experience), or a man with parrots on his shoulders are just some of the things you might see.
Get A Quick Bite (& Save Room For Dessert!)
Key West is probably most synonymous with one thing, and that thing is Key Lime Pie! Key Lime is a specific type of lime that’s more fruity and less acidic than the normal limes you can find at a grocery store. They only grow natively in, you guessed it, the Keys!
Key Lime Pie is a refreshing summer dessert, and while some people say you can get the same flavor with other limes, those pies simply won’t stack up- it’s missing the richness of flavor and always falls flat compared to the fresh Key Limes harvested in the Keys.
Something you may not know is that with Cuba being just 90-miles south of Key West, the island takes many culinary cues from their neighbor as well. To learn all about Key West’s culinary scene while sight-seeing (and, of course, eating), check out this local-led food & walking tour!
Here are some of the must-stop places on the island to grab a bite:
- Grab a Cuban Coffee: Since Cuba is so close, Key West has always been a place that attracted Cubans, and with them, Cuban culture. In the 1800s, Cubans moved to Key West to find more freedom, bringing along with them gifts to Key West like cigars and coffee. This brings us to Cuban Coffee Queen, aka the BEST coffee ever. Cuban Coffee Queen is based in a small, standalone shop- the best way to find it is by looking for a line of people waiting for coffee. Get a coffee, and maybe get a roast to go too. I always get a bag of Gallo Loco, which is chocolatey and nutty. Once you get your coffee, head to the nearby docks and sip it while watching birds dive in and out of the water.
- Breakfast, Key West Style: Once you find yourself hungry for breakfast, go to Croissants de France for some French breakfast with a Key West spin. The owner is from France and he and his wife decided to move and open up a bakery. Obviously, the croissants are amazing – big and baked to a flaky and crunchy perfection – but you must get a Key Lime Tart. Their Key Lime tart is a tangy, lightly-colored green pie with a healthy helping of meringue slathered over the top.
- Breakfast and a Show: Blue Heaven is really easy to miss (look for the sign on a gate behind some bushes), but eating at this outdoor restaurant feels like you’re inside a jungle shaded by massive banyan trees, banana palms, and colorful hibiscus flowers. The restaurant is home to cats, chickens AND baby chickens, so you just might make some animal friends while you eat! If you’ve never had fresh-caught seafood, this is the place to try it, and their Surf-N-Turf dish serves as a fantastic introduction. The fish melts in your mouth and is well seasoned with a unique blend of spices that’s slightly salty and spicy. Blue Heaven also has a Rooster Graveyard, which contains the remains of cockfighting roosters and some of Blue Heaven’s more recent rooster residents. Every morning Blue Heaven hosts local musicians playing calming music to help you start your day on the island, so grabbing breakfast here is sure to get you in the island spirit.
- Dessert that’s Better than Sex: Better Than Sex is THE romantic dessert date spot to go to. Two Key West locals opened it in 2008, and it got so popular they had to move to a bigger location the next block over within two years! While it has recently expanded out of state, this is the original and where the owners reside, so you should stop here at least once to get some sweets. I am a big lover of dessert, and let me be the bearer of good news: Better Than Sex has desserts that make me weak in the knees. Most of the desserts have fun names, like Missionary Crisp and Tongue Bath Truffle – the Kinky-er Key West Cream Pie is a good locally themed choice. Their cake is also amazing – fluffy slices piled high with icing – with delicious caramel and raspberry drizzles that, I am not ashamed to admit, I happily drown my cake in. Yum!
Meet The Ghosts of Key West
Key West is one of the most haunted cities in Florida, and the dead are said to outnumber the living here. Some say its because the limestone rock formations anchor spirits to the island, preventing them from passing into the afterlife. Or it could be because in the 1700s, Key West was mainly used by smugglers and pirates as a hideout…
Over the centuries, Key West has been home to many people, including pirates and Cuban refugees, and bears the scars of a place marked heavily by tensions between itself and the outer world, especially during the Cold War. In Key West, you can see the lasting marks of a checkered history.
I highly recommend reading native Key Wester David Sloan’s book Ghost of Key West. The book takes a deep dive into the many stories that surround Key West and the horrifying legends that some places on the island have.
Here’s where to meet a few of Key West’s notable ghosts:
- Meet Robert the Doll
You know how most of the dolls are made to be at least semi-cute? Not Robert.
Robert was made in the early 1900s, in the likeness of his owner, Robert Otto. There’s such a lack of facial details in Robert that it looks like his face has been worn down to the bare basics – beady eyes, a flat nose, lips, and most distinctively, several holes in his face due to age (he is 111 years old).
During his stay with his original owner, people reported his facial expression changing and the doll moving by himself. After his owner’s death, he was moved to the Fort East Martello Museum, where he lives today.
This doll resides with a toy dog in a case in his own room, but the freakiest thing is that the walls are plastered with letters asking for his forgiveness. The museum’s caretakers say they get about 1-3 letters a day, many of which are from people who made fun of him or took his photo without asking permission first and are now experiencing bad luck.
Speaking of that, don’t snitch to Robert that I said his eyes were beady…
- Ride the Trolley of the Doomed
The Trolley of the Doomed will take you on a late-night journey through the most haunted parts of Key West…and hope you manage to see the light of day again. This tour goes all around town and your Ghost Host will lead you on the macabre adventure of your life.
- Visit the Key West Cemetery
If you have an interest in the supernatural apparitions of Key West, the Key West Cemetery is a great place to get your spooky fix. Besides the supernatural, this cemetery contains a USS Maine memorial and another memorial dedicated to the fighters in the 1868 Cuban Revolution.
Since a large Cuban demographic existed in Key West during the time of the revolution, there was a lot of support on the island for Cuba’s fighters to win. This led to some Cuban-Americans returning to fight in the revolution, with only their bodies returning home.
Other parts of the cemetery are less serious; Key West’s dead citizens have quite the sense of humor- many of the epitaphs are sarcastic sayings and references to books and film. As a lover of The Hitchhiker’s Guide to the Galaxy, seeing a tombstone engraved with the famous quote, “So Long & Thanks For All The Fish” was hilarious. I think I’d fit in perfectly in that cemetery – I think I’d like my epitaph to read “Over My Dead Body”.
All jokes aside, if you go here, please respect the dead… or else the ghost of the cemetery might haunt you. I’ve never seen her (thankfully), but legend has it that if you disrespect the cemetery in any way, an old Bahamian woman will approach you and scold you, or threaten you if she finds you deserving of it. Also, you know, the grave-digging iguanas might get you.
The Ghost Hosts are undead guides, costumed as one of the island’s famous ghosts and more than willing to share all the gruesome details of their own death and the deaths of others on the island to you.
- Visit the Blue Heaven Rooster Cemetery
Since animals are such a big part of Key West, it’s no surprise that some of its resident critters have their own cemetery. In the aforementioned, DELICIOUS Blue Heaven restaurant, there is a small rooster cemetery!
The cemetery is dedicated to the roosters who died in cockfights, and even some of Hemingway’s six-toed cats that roam the island too (in a former life, Blue Heaven was even a pool hall, where Hemingway once refereed a boxing match).
This is probably the only restaurant in America that has a graveyard in it, but if I’m wrong, tell me – I need to see what other restaurant is wacky enough to have a cemetery in it.
Off To The (Drag) Races
Being so secluded from the mainland, Key West was largely unheard of until the 1970s, when it became a LGBTQ+ destination due to large influxes of LGBTQ+ members moving in and renovating the older homes on the island.
In the 1980s, Key West even elected one of the U.S.’s first openly gay mayors, Richard A. Heyman. With such a large presence of gay men, drag – the art of female impersonation – is a big thing on Key West.
That said, it’s important to be a courteous traveler. Visiting a gay space is exciting and fun, but be aware that it is also a space where LGBTQ+ people can express themselves safely and freely. Up until recently, gay clubs were one of the few places that LGBTQ+ people could go without fear of violence or legal consequences.
Attending a drag show is a feast for the senses: imagine the most dramatic costumes you have ever seen, fabric and feathers in all sorts of colors and patterns, over the top makeup you can see from a mile away, and incredibly defined shapes. Drag is both visual and performance art – and comedy at its finest.
You should know that drag shows are a staple of gay spaces, and oftentimes have sexual content. If you are unfamiliar with drag, check out RuPaul’s Drag Race on Hulu or check out some performances on YouTube. It’s also customary to tip your favorite drag queens, so be sure to bring some cash!
If you’re ready to have a good time, here’s where to go for a drag show:
801 Bourbon began in 1987 as a piano bar, but as time went on, the focus became less on the piano and more on the drag performances. Just one thing: at 801, the queens don’t lip-sync! They are great singers and you can listen to them dance and sing before the comedy portion of the show.
Fair warning: if you’re in the front rows, you’ll probably get teased by the queens. But hey, getting made fun of by a drag queen in front of a live audience is a gift.
If you want to get interactive, this bar has karaoke every Sunday evening! Oh, and if you happen to be in Key West on New Year’s Eve, instead of the ball drop, you can see 801’s premier Drag Queen, Sushi, dropping from a high heel shoe instead. That’s Key West for you!
Also located on Duval, Aqua isn’t just a show – it’s also a night club. This place is LOUD. I might have mentioned a few times that Duval is loud and this club is definitely one of the reasons why! Before you see the show, grab a cocktail from the bar and prepare for the show of your life.
Aqua hosts the more traditional version of drag shows, with dancing, lip-syncing, and plenty of costumes, with choreographed dances for every song. Unlike 801 Bourbon, the drag tends to focus on female illusion, the art of looking like a woman. Not to say that they don’t have costumes (one featured on the website is a queen in cow drag), but the focus is more on queens looking like queens and dancing.
Come here, see a show, and then party until the end of the night and sleep it off so you can party again the next day.
Attend a Quirky Key West Festival
For being such a small island (it has an area of about 4.2 square miles), Key West always has some sort of event going on. Check Key West’s official calendar for local plays, concerts, and games.
A friendly reminder before you decide you want to come to one: Key West festivals are multi-day affairs, with a LOT of drinking. But if you’re up for a weirdly good time, here are the two best festivals in Key West that show off everything that quirky Key West has to offer:
- Conch Republic Annual Independence Day (Mid-April)
Every April, the Conch Republic throws their 10 day independence day celebration. While this festival is about fun (drag races, costume challenges, and drunk spelling bees are all part of that), it also celebrates Key West’s environment and history.
There are naval parades and a beach clean-up, so make sure you do that to get a sense of the island beyond partying. If you want to become a Conch Republic native, buy a passport to show your status, sold by the official Conch Republic’s government website.
- Fantasy Fest (Late October)
I am a BIG fantasy nerd. I love D&D, I love dressing up, and I own a sword. (Unfortunately, it’s just a high-quality fake one, but I’m learning how to sword fight with it, so watch out.) So believe me when I say the Fantasy Fest is the PLACE for nerds like me!
People are dressed up in wild costumes- these aren’t cheap Halloween costumes, these are homemade, high-quality costumes made by people who love the art. Dragons, mermaids, princesses, and really, anything the party-goers choose to be. If you attend this festival, I’d strongly recommend bringing something to wear, even if it’s just an old Halloween costume. You don’t want to be the odd one out not wearing something fun.
I think the best part of this festival is that its goal is to help people living with HIV/AIDS and spread awareness. In the 8 weeks leading up to Fantasy Fest, there is a fundraiser for AIDS Help, a non-profit organization. Key West is historically a safe space for minorities, specifically LGBT+ members, and the island was hit hard during the 1980s AIDS epidemic.
The kickoff of the Fantasy Fest is a Coronation Ball, where the two residents who donated the most are declared King & Queen. After that, there’s 10 days of parades and contests. I’ve seen these festivals firsthand, and there is no break from the partying, not even on the “quiet” parts of the island. Oh, and if you have a pet, there’s a Pet-Owner Masquerade Challenge, where you and your pet dress up in masquerade outfits for a prize.
I lived in Florida for years, so I welcome the humidity (my hair and skin LOVE the moisture), but if you’re not used to it, you might find yourself sweating a lot. Luckily for you, the Fantasy Fest considers body paint and/or nipple pasties to be plenty of clothing, so just take off your clothes! Dates for this festival do change every year, so take a look at the Fantasy Fest website before making plans.
Psst: Love a good, quirky festival? Check out Fiesta in San Antonio, Texas! It’s a BLAST, and honestly really surprised us. Highly recommend it! You can learn more in our post about things to do in San Antonio.
Enjoy the Sunsets
The sunsets in Key West are amazing. I’m not sure what it is- maybe it’s the way the sun reflects off the water – but the sunsets aren’t one to miss. The skies turn pink and orange in the evening, and the sky slowly fades from those bright colors to a blue night with tons of stars. There isn’t a lot of light pollution in the Keys, so the stars shine brighter than they would in cities.
It really does look like something out of a painting and cameras just don’t do it justice! Here are a few ways to enjoy Key West’s incredible sunsets:
- Sunset Cruises
Sunset cruises are really popular, and I’ve gone on one every single time I’ve been to Key West. The sunset cruises normally give out free beverages – because Key West is always down to party – and are the absolute best way to see the sunset.
Most of these tours are about two hours long, returning at around 7pm. Note that since these are sailboats, the downstairs space of the boat is pretty much just a bathroom and not a space to hide from the sun, so if you burn as badly as I do make sure you bring sunblock!
If you’re traveling with your partner, book an intimate cruise like Danger’s Charters Wind & Wine Sunset Sail Sitting on a boat and watching the sunset together is such a romantic way to spend time with each other!
For a livelier evening, Cool Key West is a great choice, with local musicians playing and plenty of free drinks.
Every evening in Mallory Square, the Sunset Celebration happens! This is a really cool part about Key West- every night, performers and street artists set up booths to sell their goods and perform. You can take in the ocean breeze while celebrating the beauty of the sunset and watching people swallow swords or juggle fire.
If you (somehow) get bored of that, get your tarot cards read at a psychic booth and buy conch fritters, delicious bits of fried conch, wrapped in a thick layer of breading, garlic, and pepper.
The sunset celebration is a great way to end every day, in Key West and is the perfect way to celebrate the last evening of your visit to paradise.
What To Pack For Key West
I’m not going to tell you exactly how many dresses or pairs of shorts to pack (I trust you can figure that out on your own) BUT I do have some suggestions for must-have essentials. Throw these in your carry-on suitcase (this is our favorite!) and you’ll be all set.
- Lightweight Travel Clothesline: Avoid the dreaded beach chafe and hang your bathing suits up on this durable clothesline that fits in the palm of your hand! Tip: hang it up in front of a sunny window rather than in your damp, dark bathroom for faster drying.
- Reef-Safe Sunscreen: Going into the ocean? You’ll need to wear coral-friendly sunscreen. Unless you hate coral, fish, and also all of human life. Reef-safe sunscreen is designed to biodegrade and not harm ocean life. Regular sunscreen bleaches coral and ensures humanity’s swift death from climate change. So please, for the love of society’s inevitable collapse, don’t wear regular sunscreen in the ocean! Here’s a full-sized bottle and here’s a travel-sized version for carry-on luggage.
- Mineral Sunscreen: This is the least harmful type of sunscreen, according to science. It’s better both for your body and for the environment.
- Rash Guard: Since you’ll be snorkeling and swimming and generally spending a lot of time with your bare back facing the harsh sun, I highly recommend bringing along a rash guard, which is specially designed for swimming in salt water.
- Swim Leggings: Swim leggings let you move underwater without restriction while providing sun protection (so you don’t have to use sunscreen!) and like a bathing suit, they dry quickly and stay comfortable once you’re out of the water. I love my swim leggings (and matching top) made by Waterlust, an ethical and sustainable conservation-focused apparel company. Their marine-life themed leggings are chlorine, sun, saltwater and sunscreen resistant and made from recycled materials, and they have POCKETS! Sizes go up to 3XL. For more details about why I recommend these, head over to our Waterlust swim leggings review post!
- Snorkel Stuff: Bringing your own snorkel gear is so much more comfortable than the kit usually provided with tours, and it gives you the option to snorkel on your own at the locations recommended below! As most of the places recommended here are safe to snorkel without a tour you should throw a snorkel mask and a little bottle of anti-fog spray in your suitcase.
- Water Shoes: For every minute that you’re not wearing flippers, you’ll want to be wearing these. Whether you’re trying to walk over rocks – they’re pretty, but they hurt so bad – or just wading into some water, your un-cut feet will thank me later. I swear by my trusty Tevas, and Jeremy likes classic close-toed water shoes. A reader recently suggested these nifty water shoes that look like cute tennis shoes and can be worn in and out of the water, and we’re excited to try them out! (Here’s the dude version.) You can read more about our favorite travel shoes in our travel shoes reviews for men & for women.
- Travel Towel: I always bring a lightweight, quick-drying, packable full-sized travel towel with me to the beach! I also recommend bringing a sandproof Beach Mat to sit on.
- Quick Drying Shorts (His & Hers): Jeremy picked up a pair of these shorts to double as both his warm-weather daily clothing item and his swimsuit. They’re a 2-for-1, which is super convenient for travel, and they work great! They dry quickly, making them perfect for hopping in and out of the ocean and then resuming your normal travel activities. They never get dirty or wrinkly and always look fashionable. There’s also the women’s version, made out of the same stretchy quick-drying material as my hiking pants.
- Ultra-Light Rain Jackets (His & Hers): Our favorite rain jackets are some of the best jackets for travel. They’re ultralight and pack down into nothing so they’re easy to carry around, and they’re incredibly water repellant. They’re a perfect just-in-case item to throw in your day bag, along with a travel-friendly umbrella.
For more packing tips, check out our curvy-girl friendly beach packing list!
Where To Stay In Key West
Unless you’re planning on making the 3-hour drive from the mainland to Key West twice in one day, you’re going to need somewhere to stay. I recommend staying right in the middle of it all close to Duval Street in the beautiful, historic Old Town area.
One key thing to note, though: although there are plenty of home rentals on the island, local regulations require a 28-night minimum stay. So if you’re not a remote worker looking for a month in paradise, you’ll want to book a hotel, resort, condo, or properly licensed vacation rental. I’ve included a few picks below.
We also recommend booking directly through VRBO because it has fewer fees and more flexible cancellation policies than Airbnb – also, we’re not fans of Airbnb’s unethical track record and lax security.
- Boutique Hotel: The charming Wicker Guesthouse is located just one block from the Ernest Hemingway House, with a tropical garden and an outdoor pool. Rooms include microwaves and a small fridge, you can rent bikes on-site, and you’re only a 10-minute walk from South Beach.
- Vacation Home: The Secret Garden offers a charming private oasis, with two bedrooms, a fully stocked kitchen, and access to a shared pool.
- VRBO: The bright, sunny La Puerta Rosa home is colorful, charming, budget-friendly, and has one of the most inviting private pools I’ve ever seen – it truly looks like an island oasis. It’s in the Old Town district, so you’ll have your own private paradise and be about a mile from Duval Street. I’ve never been so tempted to pick up and move to Key West for a month as I am looking at this place.
About our Contributing Writer: Hey! I’m Haylee and I’m majoring in Economics at the University of Arizona. My end-goal is to analyze economic and social public policies, but for now, I’m focusing on surviving school and enjoying life as it comes. For me, that includes finding the weird and wacky parts of life and enjoying them as much as possible. If you like that too, then we can probably be friends.
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Which part of Key West are you most excited about? Is it the snorkeling, or the creepy living doll? Let us know where you’re heading first in the comments below!
Psst: Looking for more trips nearby? Take a look at some of our other posts:
- 10 Enchanting Things to Do in Savannah, Georgia
- The 10 Best Weekend Getaways in Florida (& Over 60 Activities!)
- How to Do Disney: A Disney Parks Guide by a Former Cast Member
- 11 Crazy Romantic Things to Do in Daytona Beach, Florida
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