10 Quirky Things To Do In Key West, Florida (& Massive Travel Guide)

Travel guide to Key West Florida! Things to do in Key West, from drag shows to ghosts to snorkeling to Key Lime Pie. Key West Florida is one of the best quirky USA travel destinations!

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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!

Psst: Planning a trip to Florida? Check out our travel guides to other places nearby:

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 late fall. By this time of year, it will be in the 80s-90s during the day and the rainy season will be ending, so you won’t have to worry as much about random showers interrupting your day. The peak summer 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 the 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).
Footbridge to the Smathers beach at sunrise in Key West, Florida.
Footbridge to the Smathers beach at sunrise in Key West, Florida. Welcome to paradise!

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 also filled with six-toed cats. I blame Ernest Hemingway, who lived there and had a 6-toed cat, so it’s likely a lot of the cats on the island are related. 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.
Private beach in Key West, Florida
Be sure to pack plenty of reef-safe sunscreen, to protect Key West’s native underwater habitats and ecosystems!

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. There are even swim leggings made from swimwear material, which is perfect because my butt is always the first thing to burn when I’m snorkeling. This cuts down on the amount of sunscreen you need, which is a win/win since I hate wearing sunscreen and it’s not great for marine life!
  • 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 2-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 AirBnBs 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.

  • 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.
  • AirBnB: The bright, sunny Sugarpoppy Cottage is colorful, charming, budget-friendly, and has one of the most inviting private pools I’ve ever seen – just steps from the bedroom. It’s just a block from Duval Street, so you’ll have your own private oasis in the center of it all. I’ve never been so tempted to pick up and move to Key West for a month as I am looking at this place.

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, and the Humphead Parrotfish are larger and rarer. 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. 
Coastline of Fort Zachary State Park in Key West, Florida
Fort Zachary State Park is one of the best places to spend a day snorkeling and playing on the beach in Key West, Florida.

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!
Outside of the Audubon House in Key West, Florida.
The Audubon House is named for white supremacist and bird enthusiast John Audubon, but was originally home to a wealthy shipwreck scavenger who made his money selling pillaged valuables. Photo Credit

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:

Ernest Hemingway House in Key West, Florida
The Hemingway House! You may or may not be a fan of Hemingway’s “manly” writing and reputed womanizing, but you can’t deny that his house and its resident cats are pretty cute. Photo Credit

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.

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